JP5646345B2 - 1,5−ジアミノペンタンの発酵産生方法 - Google Patents
1,5−ジアミノペンタンの発酵産生方法 Download PDFInfo
- Publication number
- JP5646345B2 JP5646345B2 JP2010543506A JP2010543506A JP5646345B2 JP 5646345 B2 JP5646345 B2 JP 5646345B2 JP 2010543506 A JP2010543506 A JP 2010543506A JP 2010543506 A JP2010543506 A JP 2010543506A JP 5646345 B2 JP5646345 B2 JP 5646345B2
- Authority
- JP
- Japan
- Prior art keywords
- dap
- process according
- lysine
- fermentation broth
- fermentation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 81
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000012262 fermentative production Methods 0.000 title claims abstract description 5
- 238000000855 fermentation Methods 0.000 claims abstract description 63
- 230000004151 fermentation Effects 0.000 claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims description 55
- 239000004472 Lysine Substances 0.000 claims description 42
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 34
- 244000005700 microbiome Species 0.000 claims description 25
- 238000000605 extraction Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- 108010048581 Lysine decarboxylase Proteins 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000005191 phase separation Methods 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 239000001963 growth medium Substances 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- 238000002955 isolation Methods 0.000 claims description 9
- 238000003776 cleavage reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000007017 scission Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000000306 component Substances 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 230000001413 cellular effect Effects 0.000 claims description 3
- 239000012533 medium component Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000021962 pH elevation Effects 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 235000010633 broth Nutrition 0.000 abstract description 35
- 235000019838 diammonium phosphate Nutrition 0.000 abstract 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 42
- 108090000623 proteins and genes Proteins 0.000 description 28
- 235000018977 lysine Nutrition 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
- 230000001105 regulatory effect Effects 0.000 description 15
- 230000014509 gene expression Effects 0.000 description 14
- 239000002609 medium Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 241000186226 Corynebacterium glutamicum Species 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000019766 L-Lysine Nutrition 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 239000013600 plasmid vector Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000013598 vector Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000010923 batch production Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000011144 upstream manufacturing Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 241000186031 Corynebacteriaceae Species 0.000 description 5
- 241000186216 Corynebacterium Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000007523 nucleic acids Chemical group 0.000 description 5
- 239000013612 plasmid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 108091026890 Coding region Proteins 0.000 description 4
- 108091028043 Nucleic acid sequence Proteins 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229940041514 candida albicans extract Drugs 0.000 description 4
- 238000010367 cloning Methods 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- -1 for example Polymers 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012092 media component Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 230000010076 replication Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 239000012138 yeast extract Substances 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000002074 deregulated effect Effects 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000002068 genetic effect Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002906 microbiologic effect Effects 0.000 description 3
- 235000013379 molasses Nutrition 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- QWQYKTQEIQKCQM-UHFFFAOYSA-N 5,5-diaminoheptan-2-one Chemical compound C(C)(=O)CCC(CC)(N)N QWQYKTQEIQKCQM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 241000186146 Brevibacterium Species 0.000 description 2
- 108090000489 Carboxy-Lyases Proteins 0.000 description 2
- 102000004031 Carboxy-Lyases Human genes 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000001851 biosynthetic effect Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012539 chromatography resin Substances 0.000 description 2
- 210000000349 chromosome Anatomy 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000003831 deregulation Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000002018 overexpression Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GMKMEZVLHJARHF-UHFFFAOYSA-N 2,6-diaminopimelic acid Chemical compound OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101100298079 African swine fever virus (strain Badajoz 1971 Vero-adapted) pNG2 gene Proteins 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 101150086876 Amy gene Proteins 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 108020004638 Circular DNA Proteins 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241001517047 Corynebacterium acetoacidophilum Species 0.000 description 1
- 241001485655 Corynebacterium glutamicum ATCC 13032 Species 0.000 description 1
- 241000807905 Corynebacterium glutamicum ATCC 14067 Species 0.000 description 1
- 241000133018 Corynebacterium melassecola Species 0.000 description 1
- 241000337023 Corynebacterium thermoaminogenes Species 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 1
- 230000004544 DNA amplification Effects 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 101100465553 Dictyostelium discoideum psmB6 gene Proteins 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100398755 Escherichia coli (strain K12) ldcC gene Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108700007698 Genetic Terminator Regions Proteins 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100169519 Pyrococcus abyssi (strain GE5 / Orsay) dapAL gene Proteins 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 108010039491 Ricin Proteins 0.000 description 1
- 229910003798 SPO2 Inorganic materials 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 101100478210 Schizosaccharomyces pombe (strain 972 / ATCC 24843) spo2 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000010364 biochemical engineering Methods 0.000 description 1
- 230000008238 biochemical pathway Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical group C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 101150008667 cadA gene Proteins 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 230000002759 chromosomal effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 241000186254 coryneform bacterium Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 101150011371 dapA gene Proteins 0.000 description 1
- 101150057904 ddh gene Proteins 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 238000012239 gene modification Methods 0.000 description 1
- 230000005017 genetic modification Effects 0.000 description 1
- 235000013617 genetically modified food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 101150041134 ldcC gene Proteins 0.000 description 1
- 101150109073 ldhD gene Proteins 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 101150033534 lysA gene Proteins 0.000 description 1
- 101150035025 lysC gene Proteins 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000013586 microbial product Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 238000001320 near-infrared absorption spectroscopy Methods 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical compound CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011426 transformation method Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1. 好ましい実施形態
本発明は、DAP含有発酵ブロスからの1,5-ジアミノペンタン(DAP)の単離プロセスに関する。このプロセスでは、a)発酵ブロスをアルカリ化し、b)発酵ブロスを熱処理し、c)DAPを有機抽出剤で抽出し、そしてd)取り出された有機相からDAPを単離する。
2.1 微生物
本発明は、原理的には、任意のDAP含有発酵ブロスの後処理に適用可能である。また、原理的には、発酵で利用される微生物に関してなんの制限もない。後者は、天然に存在する微生物、突然変異および選択により改良された微生物、とくに組換えにより産生された微生物、たとえば菌類、とくに細菌でありうる。これらの微生物は、DAPおよび/もしくはDAP誘導体たとえばアセチル-DAPを直接産生しうるか、または少なくともリシンとくにL-リシンを発酵産生しうるかのいずれかである。より特定的には、利用される組換え細菌は、ジアミノピメリン酸経路(「DAP経路」)、スクシニラーゼ経路、またはデヒドロゲナーゼ経路を介してリシンを生合成することが可能である。
コリネバクテリウム・グルタミカム(Corynebacterium glutamicum) ATCC 13032、
コリネバクテリウム・アセトグルタミカム(Corynebacterium acetoglutamicum) ATCC 15806、
コリネバクテリウム・アセトアシドフィラム(Corynebacterium acetoacidophilum) ATCC 13870、
コリネバクテリウム・サーモアミノゲネス(Corynebacterium thermoaminogenes) FERM BP-1539、
コリネバクテリウム・メラセコラ(Corynebacterium melassecola) ATCC 17965、
もしくは
ブレビバクテリウム(Brevibacterium)属の株、たとえば、
ブレビバクテリウム・フラバム(Brevibacterium flavum) ATCC 14067、
ブレビバクテリウム・ラクトファーメンタム(Brevibacterium lactofermentum) ATCC 13869、および
ブレビバクテリウム・ディバリカタム(Brevibacterium divaricatum) ATCC 14020、
またはそれらに由来する株、たとえば、
コリネバクテリウム・グルタミカム(Corynebacterium glutamicum) KFCC10065、
コリネバクテリウム・グルタミカム(Corynebacterium glutamicum) ATCC21608
である。
本発明に従って後処理される発酵ブロスは、たとえば、組換えコリネ型細菌の培養に由来する。この組換えコリネ型細菌は、リシン生合成を促進しかつ少なくとも1つのリシン生合成遺伝子に影響を及ぼすデレギュレート介入を介して、リシンとくにL-リシンもしくはリシン含有混合物の産生を増大させ、かつ/またはリシンデカルボキシラーゼ活性を有する酵素の追加的過剰発現ならびにDAPおよび/もしくはアセチル-DAPの蓄積を行う。したがって、後者は、DAPを直接産生することが可能である。
次に、公知の方法により、たとえば、回転式蒸発器、薄膜式蒸発器、流下膜式蒸発器を用いて、逆浸透により、またはナノ濾過により、発酵ブロスを濃厚化または濃縮することが可能である。必要であれば、濃縮手順に基づいて沈澱させたものでありうる塩を、たとえば濾過または遠心分離により取り出すことが可能である。次に、この濃縮された発酵ブロスを本発明に係る方式で後処理してDAPを得ることが可能である。本発明に係る後処理のために、そのような濃縮手順が利用可能であるが、絶対に必要であるというわけではない。
それ自体公知のDAP産生株のストック培養物(本明細書で明示的に参照される国際公開第2007/113127号パンフレットの14頁の実施例2を参照されたい)(-80℃で貯蔵)から細胞のアリコートを取得し、ペトリ皿中の固体培地(特定の培地組成(表2参照))上に画線し(培養物1)、次に、30℃で72時間インキュベートした。このようにして得られた細胞を濃度0.9%のNaCl溶液中に入れ、ペトリ皿中の固体培地上に再び画線し(培養物2)、次に、30℃でさらに24時間インキュベートした。次に、接種ループを用いてペトリ皿(培養物2)から細胞を採取して、2つのバッフルを有する2Lシェーカーフラスコ中の200ml(プレート培地およびバッチ培地に類似した組成)に接種し、そしてオービタルシェーカーを用いて250rpmおよび30℃で24時間インキュベートした。
a) 熱処理および抽出手順(単一バッチ)
NaOHでpH13.5に調整された750kg(670L)の無細胞発酵ブロスを1m3ステンレス鋼タンクに充填した。反応器内容物を還流温度(約103℃)に加熱して5時間還流した。プロセスで生成されたアンモニア含有排ガスをガス洗浄器(洗浄液としての水を使用)に通して捕集した。60℃に冷却した後、140kgのn-ブタノールを供給導入し、続いて60℃で15分間攪拌し、そして混合物を2時間静置した。相分離後、下側水性相を1m3容器内に排出した。有機相を他の容器内に捕集した。いずれの場合も35Lの脱イオン水を添加した後、いずれの場合も140kgのn-ブタノールを用いて水性相を60℃でさらに2回抽出した。
塔(理論段数4段)に取り付けられた1m3ステンレス鋼タンクに抽出(サブ工程a)からの合わせた有機相の900kgの初期仕込みを行った。水/n-BuOHを留去しながら、さらなる1400kgの抽出溶液を一定体積で供給導入した。次に、圧力を200mbarに低下させ、360kgの底部生成物が残留した状態になるまで混合物を蒸留した。
種々の時間点で底部バルブを介して二相サンプルを取り出して脱混合後ただちに相を分離することにより、本発明に従って調製された有機DAP抽出物の分配平衡の確立について60℃で強力に攪拌しながら2.5L反応器内で調べた。所要のサンプル静置時間に起因するある程度の不正確さにも関わらず、分配は、非常に迅速に起こると結論付けることが可能である。すなわち、15秒後に、サンプルは、5分後に見いだされたDAPの98.5%を有していた。したがって、15分間の追加の撹拌を行えば十分であるとみなすことが可能である。
三段ビームアジテーターと4つのバッフルとを有する2.5L二重壁ジャケット反応器内で相分離速度を調べた。
プロデューサー生物は、形成されたDAPの一部分を2つのアミノ基のいずれかにおいて追加的にアセチル化することが観測された。
いずれの場合も、本発明に従って調製されたpH13.0の発酵ブロス300mlを、インペラー撹拌機付き0.75L二重壁ジャケット反応器内で、60℃で3回、熱処理後に、いずれの場合も100mlのn-BuOH(水飽和)と共に350rpmで攪拌した後、抽出した。結果を表5にまとめる。
いずれの場合も、本発明に従って調製された2kgの発酵ブロスにDAPを添加してDAP含有率を10%に増加させ、NaOHを添加することによりpHを11.0、12.0、または13.5に調整した。いずれの場合も、60℃で150gの水飽和n-BuOHで5回抽出することにより、分配係数を決定した。分析により決定された水性相および有機相のDAP含有率ならびに分配係数を表6に列挙する。
0.75L二重壁ジャケット反応器内で、いずれの場合も、高AcDAP含有率を有する本発明に従って調製された500gの発酵ブロスを濃度50%のNaOHの添加により所望のpHに調整し、そして還流温度に加熱した。0.5、1、2、および4時間後、サンプルを採取して定量的HPLCにより測定した。結果を表7にまとめる。
本発明に従って調製された約4.1重量%のDAP含有率を有する130gの抽出相に、70gの水飽和ブタノール中の7.2gのアジピン酸の溶液を25〜30℃で滴下した。反応混合物を3℃に冷却し、固形分を濾別し、そして窒素ストリーム中で一晩乾燥させた。これにより12.7gの白色固体を得た。この固体は、13C-NMRによりアジピン酸とDAPとの1:1混合物であると特徴付けられた。
Claims (25)
- a)発酵ブロスをpH>11に調整することによりアルカリ化し、b)前記アルカリ化発酵ブロスを熱処理し、c)DAPを有機抽出剤で抽出し、そしてd)取り出された有機相からDAPを単離する、DAP含有発酵ブロスからの1,5-ジアミノペンタン(DAP)の単離プロセスであって、前記ステップb)の熱処理を、アセチル-DAPの加水分解切断を引き起こす条件下で、前記抽出ステップc)における相分離を補助するのに十分な時間行う、上記プロセス。
- pHがpH≧12に調整される、請求項1に記載のプロセス。
- 前記pHを、アルカリ金属水酸化物またはアルカリ土類金属水酸化物を添加することにより調整する、請求項1または2に記載のプロセス。
- 前記アルカリ化された発酵ブロスを、還流温度に加熱することにより熱処理する、請求項1〜3のいずれか1項に記載のプロセス。
- 前記還流温度が、大気圧で90〜110℃の範囲の温度に相当する、請求項4に記載のプロセス。
- アルカリ化発酵ブロスが、少なくとも0.5時間熱処理される、請求項1〜5のいずれか1項に記載のプロセス。
- DAPを双極性プロトン性有機溶媒で抽出する、請求項1〜6のいずれか1項に記載のプロセス。
- 前記抽出剤がアルカノールまたはシクロアルカノールである、請求項7に記載のプロセス。
- 前記抽出および/または後続の相分離を高温で行う、請求項7および8のいずれか1項に記載のプロセス。
- 細胞成分をアルカリ化前に前記発酵ブロスから除去する、請求項1〜9のいずれか1項に記載のプロセス。
- 前記抽出工程のDAP含有相を蒸留により精製するか、またはDAPをそれから沈澱させる、請求項1〜10のいずれか1項に記載のプロセス。
- 前記発酵ブロスが、複合培地成分を含む培養培地中での微生物の発酵に由来する、請求項1〜11のいずれか1項に記載のプロセス。
- リシン産生条件下でリシン産生微生物を培養し、形成されたDAPを、請求項1〜12のいずれか1項に記載のプロセスを適用することにより単離する、DAPの発酵産生プロセス。
- DAP産生条件下でリシン産生微生物を培養する、請求項13に記載のプロセス。
- 前記発酵を、複合培地成分を含む培養培地中で行う、請求項13または14に記載のプロセス。
- 前記リシン産生微生物がリシンデカルボキシラーゼ活性を含む、請求項13〜15のいずれか1項に記載のプロセス。
- 前記リシン産生微生物が異種リシンデカルボキシラーゼを含む、請求項16に記載のプロセス。
- 前記リシン産生微生物が異種リシンデカルボキシラーゼ遺伝子を含む、請求項16および17のいずれか1項に記載のプロセス。
- リシンを脱カルボキシル化してDAPを得るために、前記リシン含有発酵ブロスをリシンデカルボキシラーゼと接触させる、請求項13〜15のいずれか1項に記載のプロセス。
- リシンデカルボキシラーゼが固定されている、請求項19に記載のプロセス。
- 最初に、請求項1〜20のいずれか1項に記載のプロセスによりDAPモノマーの発酵産生および単離を行い、次に、少なくとも1つのさらなるコモノマーと一緒に重合を行う、DAP含有ポリマーの調製プロセス。
- 前記コモノマーが、ポリイソシアネートおよびポリカルボン酸、ならびにそれらの塩、エステル、およびアンヒドリドの中から選択される、請求項21に記載のプロセス。
- 前記単離されたDAPに少なくとも1つのコモノマーを添加するか、またはDAPとDAP沈殿からの少なくとも1つのコモノマーとの混合物を利用する、請求項21または22に記載のプロセス。
- 前記DAP/コモノマー混合物が請求項11に記載の塩析沈殿により生成される、請求項23に記載のプロセス。
- 前記コモノマーがポリカルボン酸である、請求項24に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08150575 | 2008-01-23 | ||
EP08150575.2 | 2008-01-23 | ||
PCT/EP2009/050778 WO2009092793A2 (de) | 2008-01-23 | 2009-01-23 | Verfahren zur fermentativen herstellung von 1,5-diaminopentan |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011509679A JP2011509679A (ja) | 2011-03-31 |
JP5646345B2 true JP5646345B2 (ja) | 2014-12-24 |
Family
ID=40793078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010543506A Active JP5646345B2 (ja) | 2008-01-23 | 2009-01-23 | 1,5−ジアミノペンタンの発酵産生方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8906653B2 (ja) |
EP (1) | EP2235194B1 (ja) |
JP (1) | JP5646345B2 (ja) |
KR (1) | KR101579994B1 (ja) |
CN (1) | CN101981202B (ja) |
AT (1) | ATE517190T1 (ja) |
PL (1) | PL2235194T3 (ja) |
WO (1) | WO2009092793A2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022244809A1 (ja) | 2021-05-19 | 2022-11-24 | 旭化成株式会社 | ジアミン生産能を有する組換え微生物およびジアミンの製造方法 |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009095441A1 (de) * | 2008-01-31 | 2009-08-06 | Basf Se | Faserverstärkte polyamid[5,10] formmassen |
US8647642B2 (en) | 2008-09-18 | 2014-02-11 | Aviex Technologies, Llc | Live bacterial vaccines resistant to carbon dioxide (CO2), acidic PH and/or osmolarity for viral infection prophylaxis or treatment |
CN102712569A (zh) * | 2009-12-17 | 2012-10-03 | 巴斯夫欧洲公司 | 纯化含氨基化合物的方法 |
WO2011108473A1 (ja) * | 2010-03-01 | 2011-09-09 | 三井化学株式会社 | 1,5-ペンタメチレンジアミンの製造方法、1,5-ペンタメチレンジアミン、1,5-ペンタメチレンジイソシアネート、1,5-ペンタメチレンジイソシアネートの製造方法、ポリイソシアネート組成物、および、ポリウレタン樹脂 |
WO2012121291A1 (ja) | 2011-03-09 | 2012-09-13 | 三井化学株式会社 | ペンタメチレンジイソシアネート、ペンタメチレンジイソシアネートの製造方法、ポリイソシアネート組成物、ポリウレタン樹脂およびポリウレア樹脂 |
KR101286158B1 (ko) * | 2011-08-24 | 2013-07-15 | 씨제이제일제당 (주) | 발효액에서 1,4-디아미노부탄의 분리 및 정제하는 방법 |
KR20140052189A (ko) * | 2012-10-22 | 2014-05-07 | 씨제이제일제당 (주) | 1,4-디아미노부탄의 정제방법, 상기 방법으로 정제된 1,4-디아미노부탄 및 이로부터 제조되는 폴리아미드 |
CN105612257B (zh) * | 2013-01-28 | 2020-03-17 | 上海凯赛生物技术股份有限公司 | 使用高沸点溶剂的尸胺纯化 |
US9914694B2 (en) | 2013-01-28 | 2018-03-13 | Cathay R&D Center Co., Ltd. | Purification of cadaverine using high boiling point solvent |
US9896409B2 (en) | 2013-01-28 | 2018-02-20 | Cathay R&D Center Co., Ltd. | Purification of cadaverine using high boiling point solvent |
WO2015076238A1 (ja) * | 2013-11-19 | 2015-05-28 | 東レ株式会社 | 1,5-ペンタメチレンジアミンおよびその製造方法 |
KR20150115533A (ko) * | 2014-04-04 | 2015-10-14 | 씨제이제일제당 (주) | 1,5-디아미노펜탄의 정제방법 |
CN106795543A (zh) * | 2014-07-31 | 2017-05-31 | 卡尔斯鲁厄技术研究所 | 用于生产塑料的预聚物的酶催化生产方法 |
BR112017013748A2 (pt) * | 2014-12-23 | 2018-03-13 | Genomatica Inc | método de produção & processamento de diaminas |
WO2016119230A1 (en) | 2015-01-30 | 2016-08-04 | Cathay R & D Center Co., Ltd. | Expression of klebsiella oxytoca polypeptides involved in lysine decarboxylation, and methods and applications thereof |
US20160297747A1 (en) | 2015-04-08 | 2016-10-13 | Invista North America S.A.R.L. | Materials and methods for the selective recovery of monovalent products from aqueous solutions using continuous ion exchange |
EP3286273B1 (de) | 2015-04-20 | 2019-07-24 | Basf Se | Zweikomponentige beschichtungsmassen |
KR101773135B1 (ko) * | 2015-05-08 | 2017-08-30 | 씨제이제일제당 주식회사 | 1,4-디아미노부탄의 정제방법 |
CN107043330B (zh) * | 2016-02-06 | 2020-10-20 | 上海凯赛生物技术股份有限公司 | 一种从含1,5-戊二胺盐的溶液体系中提取1,5-戊二胺的方法 |
CN105861586B (zh) * | 2016-05-16 | 2017-05-24 | 宁夏伊品生物科技股份有限公司 | 包括二氧化碳脱除工艺的发酵生产戊二胺的方法 |
CN106367326B (zh) * | 2016-07-28 | 2018-10-30 | 南京工业大学 | 一种固定化细胞连续生产萃取戊二胺的装置 |
CN107779445B (zh) * | 2016-08-25 | 2021-02-19 | 上海凯赛生物技术股份有限公司 | 固定化赖氨酸脱羧酶、其制备、1,5-戊二胺制备方法及产品 |
CN107779446B (zh) * | 2016-08-25 | 2021-09-07 | 上海凯赛生物技术股份有限公司 | 固定化赖氨酸脱羧酶、其制备、1,5-戊二胺制备方法及产品 |
US11129906B1 (en) | 2016-12-07 | 2021-09-28 | David Gordon Bermudes | Chimeric protein toxins for expression by therapeutic bacteria |
US11180535B1 (en) | 2016-12-07 | 2021-11-23 | David Gordon Bermudes | Saccharide binding, tumor penetration, and cytotoxic antitumor chimeric peptides from therapeutic bacteria |
US10464880B2 (en) | 2017-01-27 | 2019-11-05 | Cathay Biotech Inc. | Purification of cadaverine using high boiling point solvent |
KR102094348B1 (ko) | 2017-10-18 | 2020-03-27 | 씨제이제일제당 주식회사 | 1,5-디아미노펜탄의 정제방법 |
CN107880543A (zh) * | 2017-12-11 | 2018-04-06 | 苏州天亦辰针织有限公司 | 一种生物基尼龙面料及其制备工艺 |
CN108997130A (zh) * | 2018-08-29 | 2018-12-14 | 南京工业大学 | 一种1,5-戊二胺萃取和成盐耦合的方法 |
EP3852923A1 (en) * | 2018-09-18 | 2021-07-28 | INVISTA Textiles (U.K.) Limited | Systems and methods for recovering amines and their derivates from aqueous mixtures |
CN109704978A (zh) * | 2018-12-25 | 2019-05-03 | 天津大学 | 一种戊二胺的纯化方法 |
IT202100007331A1 (it) * | 2021-03-25 | 2022-09-25 | Univ Bologna Alma Mater Studiorum | Procedimento di estrazione di poliammine da matrici naturali complesse |
CN115611748B (zh) * | 2021-07-14 | 2024-07-05 | 上海凯赛生物技术股份有限公司 | 一种1,5-戊二胺的分离方法 |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5835197A (ja) * | 1981-08-26 | 1983-03-01 | Kyowa Hakko Kogyo Co Ltd | プラスミドpcg2 |
US4601893A (en) * | 1984-02-08 | 1986-07-22 | Pfizer Inc. | Laminate device for controlled and prolonged release of substances to an ambient environment and method of use |
GB2165546B (en) * | 1984-08-21 | 1989-05-17 | Asahi Chemical Ind | A plasmid containing a gene for tetracycline resistance and dna fragments derived therefrom |
JPH01131275A (ja) * | 1987-11-16 | 1989-05-24 | Mitsui Petrochem Ind Ltd | ポリアミド組成物 |
DE4027453A1 (de) * | 1990-08-30 | 1992-03-05 | Degussa | Neue plasmide aus corynebacterium glutamicum und davon abgeleitete plasmidvektoren |
DE4440118C1 (de) | 1994-11-11 | 1995-11-09 | Forschungszentrum Juelich Gmbh | Die Genexpression in coryneformen Bakterien regulierende DNA |
US6238896B1 (en) * | 1997-02-20 | 2001-05-29 | Mitsubishi Rayon Co., Ltd. | Process for producing malonic acid derivatives |
JPH10229891A (ja) | 1997-02-20 | 1998-09-02 | Mitsubishi Rayon Co Ltd | マロン酸誘導体の製造法 |
JP2002223771A (ja) | 2001-02-01 | 2002-08-13 | Toray Ind Inc | カダベリンの製造方法 |
JP4196620B2 (ja) | 2002-04-08 | 2008-12-17 | 東レ株式会社 | ポリアミド原料用カダベリンの製造方法 |
JP4356320B2 (ja) * | 2003-01-08 | 2009-11-04 | 東レ株式会社 | カダベリン・ジカルボン酸塩およびポリアミドの製造方法 |
JP2004222569A (ja) | 2003-01-22 | 2004-08-12 | Toray Ind Inc | コリネ型細菌、ならびにカダベリンもしくはその塩およびそれらの製造方法 |
ATE318926T1 (de) * | 2003-05-26 | 2006-03-15 | Ajinomoto Kk | Verfahren zur herstellung von cadaverindicarboxylat und dessen verwendung zur herstellung von nylon |
DE102004061846A1 (de) * | 2004-12-22 | 2006-07-13 | Basf Ag | Mehrfachpromotoren |
WO2006123778A1 (ja) * | 2005-05-19 | 2006-11-23 | Ajinomoto Co., Inc. | カダベリン炭酸塩の製造法、及びそれを利用したポリアミドの製造法 |
CN102732578B (zh) * | 2006-03-30 | 2016-02-17 | 巴斯夫欧洲公司 | 生产尸胺的方法 |
BRPI0712219A2 (pt) | 2006-05-24 | 2012-03-13 | Evonik Degussa Gmbh | processo para a preparação de l-metionina |
JP2009545553A (ja) * | 2006-08-01 | 2009-12-24 | ビーエーエスエフ ソシエタス・ヨーロピア | ペンタメチレン−1,5−ジイソシアネートの製造方法 |
US20090325244A1 (en) * | 2006-10-24 | 2009-12-31 | Basf Se | Method of increasing gene expression using modified codon usage |
US20100041107A1 (en) * | 2006-10-24 | 2010-02-18 | Basf Se | Method of reducing gene expression using modified codon usage |
US8252555B2 (en) | 2006-12-29 | 2012-08-28 | Evonik Degussa Ag | Nucleic acid encoding a cobalamin-dependent methionine synthase polypeptide |
DE102007005072A1 (de) * | 2007-02-01 | 2008-08-07 | Evonik Degussa Gmbh | Verfahren zur fermentativen Herstellung von Cadaverin |
EP2121735A1 (en) | 2007-02-19 | 2009-11-25 | Evonik Degussa GmbH | Method of producing methionine in corynebacteria by over-expressing enzymes of the pentose phosphate pathway |
WO2008101857A2 (en) | 2007-02-19 | 2008-08-28 | Evonik Degussa Gmbh | Coryneform bacteria with formate-thf-synthetase and/or glycine cleavage activity |
CN101849017A (zh) | 2007-06-15 | 2010-09-29 | 赢创德固赛有限责任公司 | 具有下调的维生素b12***的微生物 |
WO2009095440A1 (de) | 2008-01-31 | 2009-08-06 | Basf Se | Transparente polyamid[5,10] formmassen |
WO2009095441A1 (de) * | 2008-01-31 | 2009-08-06 | Basf Se | Faserverstärkte polyamid[5,10] formmassen |
BRPI0908458A2 (pt) | 2008-02-04 | 2015-08-18 | Basf Se | Método para a produção fermentativa de dipicolinato, sequência de ácido nucleico, cassete de expressão, vetor recombinante, hospedeiro procariótico ou eucariótico, e, método para preparar um polímero. |
-
2009
- 2009-01-23 EP EP09704118A patent/EP2235194B1/de active Active
- 2009-01-23 AT AT09704118T patent/ATE517190T1/de active
- 2009-01-23 WO PCT/EP2009/050778 patent/WO2009092793A2/de active Application Filing
- 2009-01-23 KR KR1020107018517A patent/KR101579994B1/ko active IP Right Grant
- 2009-01-23 CN CN2009801105629A patent/CN101981202B/zh active Active
- 2009-01-23 PL PL09704118T patent/PL2235194T3/pl unknown
- 2009-01-23 US US12/864,176 patent/US8906653B2/en active Active
- 2009-01-23 JP JP2010543506A patent/JP5646345B2/ja active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022244809A1 (ja) | 2021-05-19 | 2022-11-24 | 旭化成株式会社 | ジアミン生産能を有する組換え微生物およびジアミンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20100292429A1 (en) | 2010-11-18 |
KR20100117084A (ko) | 2010-11-02 |
KR101579994B1 (ko) | 2015-12-24 |
CN101981202B (zh) | 2013-09-11 |
US8906653B2 (en) | 2014-12-09 |
WO2009092793A2 (de) | 2009-07-30 |
JP2011509679A (ja) | 2011-03-31 |
CN101981202A (zh) | 2011-02-23 |
PL2235194T3 (pl) | 2011-12-30 |
ATE517190T1 (de) | 2011-08-15 |
EP2235194A2 (de) | 2010-10-06 |
WO2009092793A3 (de) | 2009-10-15 |
EP2235194B1 (de) | 2011-07-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5646345B2 (ja) | 1,5−ジアミノペンタンの発酵産生方法 | |
KR100889434B1 (ko) | 메티오닌 생산 방법 | |
US20070218526A1 (en) | Method for zymotic production of fine chemicals containing sulphur (metA) | |
US20050266535A1 (en) | Nucleotide sequences which code for the metE gene | |
US7635580B2 (en) | Method for the production of sulpher-containing fine chemicals by fermentation | |
US7485444B2 (en) | Methods for producing sulphurous fine chemicals by fermentation using metH-coding cornyeform bacteria | |
EP2085482B1 (en) | Nucleotide sequences which code for the metY gene | |
US7282357B2 (en) | Method for the production by fermentation of sulphur-containing fine chemicals (metF) | |
CN100523208C (zh) | 发酵产生含硫精细化学品的方法(metY) | |
US20050064551A1 (en) | Nucleotide sequences which code for the metY gene |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120119 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131029 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140123 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140130 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140428 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141007 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141105 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5646345 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |