CN111187792A - 乙基己基甘油的制备方法 - Google Patents
乙基己基甘油的制备方法 Download PDFInfo
- Publication number
- CN111187792A CN111187792A CN201811353198.6A CN201811353198A CN111187792A CN 111187792 A CN111187792 A CN 111187792A CN 201811353198 A CN201811353198 A CN 201811353198A CN 111187792 A CN111187792 A CN 111187792A
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- China
- Prior art keywords
- preparing
- ala
- whole
- ethylhexyl
- gly
- Prior art date
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- ANZUDYZHSVGBRF-UHFFFAOYSA-N 3-ethylnonane-1,2,3-triol Chemical compound CCCCCCC(O)(CC)C(O)CO ANZUDYZHSVGBRF-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical group CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000000758 substrate Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000007853 buffer solution Substances 0.000 claims abstract description 3
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 241000894006 Bacteria Species 0.000 claims description 36
- 108090000623 proteins and genes Proteins 0.000 claims description 28
- NCZPCONIKBICGS-UHFFFAOYSA-N 3-(2-ethylhexoxy)propane-1,2-diol Chemical compound CCCCC(CC)COCC(O)CO NCZPCONIKBICGS-UHFFFAOYSA-N 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 239000001963 growth medium Substances 0.000 claims description 15
- 239000002609 medium Substances 0.000 claims description 15
- 102000005486 Epoxide hydrolase Human genes 0.000 claims description 14
- 108020002908 Epoxide hydrolase Proteins 0.000 claims description 14
- 229940100524 ethylhexylglycerin Drugs 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 238000000855 fermentation Methods 0.000 claims description 10
- 230000004151 fermentation Effects 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 239000001888 Peptone Substances 0.000 claims description 6
- 108010080698 Peptones Proteins 0.000 claims description 6
- 229940041514 candida albicans extract Drugs 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 235000019319 peptone Nutrition 0.000 claims description 6
- 230000001954 sterilising effect Effects 0.000 claims description 6
- 239000012138 yeast extract Substances 0.000 claims description 6
- 241001198387 Escherichia coli BL21(DE3) Species 0.000 claims description 5
- 239000013604 expression vector Substances 0.000 claims description 5
- 238000011218 seed culture Methods 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 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 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 3
- 229920001817 Agar Polymers 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 241000186216 Corynebacterium Species 0.000 claims description 3
- 241000588722 Escherichia Species 0.000 claims description 3
- 241000223218 Fusarium Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 241000235070 Saccharomyces Species 0.000 claims description 3
- 239000008272 agar Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- SPOMEWBVWWDQBC-UHFFFAOYSA-K tripotassium;dihydrogen phosphate;hydrogen phosphate Chemical compound [K+].[K+].[K+].OP(O)([O-])=O.OP([O-])([O-])=O SPOMEWBVWWDQBC-UHFFFAOYSA-K 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims description 2
- 238000005520 cutting process Methods 0.000 claims description 2
- 239000000411 inducer Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- 239000012535 impurity Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000009467 reduction Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 9
- 239000000872 buffer Substances 0.000 description 8
- 230000006698 induction Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 238000010353 genetic engineering Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 241000233540 Novosphingobium aromaticivorans Species 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000002335 preservative effect Effects 0.000 description 5
- GZYNMZQXFRWDFH-YTWAJWBKSA-N Thr-Arg-Pro Chemical compound C[C@H]([C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@@H]1C(=O)O)N)O GZYNMZQXFRWDFH-YTWAJWBKSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 108010036413 histidylglycine Proteins 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- HQSKKSLNLSTONK-JTQLQIEISA-N Gly-Tyr-Gly Chemical compound OC(=O)CNC(=O)[C@@H](NC(=O)CN)CC1=CC=C(O)C=C1 HQSKKSLNLSTONK-JTQLQIEISA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 108010045126 glycyl-tyrosyl-glycine Proteins 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000013598 vector Substances 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- DKJPOZOEBONHFS-ZLUOBGJFSA-N Ala-Ala-Asp Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@H](C(O)=O)CC(O)=O DKJPOZOEBONHFS-ZLUOBGJFSA-N 0.000 description 2
- YYSWCHMLFJLLBJ-ZLUOBGJFSA-N Ala-Ala-Ser Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(O)=O YYSWCHMLFJLLBJ-ZLUOBGJFSA-N 0.000 description 2
- IFTVANMRTIHKML-WDSKDSINSA-N Ala-Gln-Gly Chemical compound C[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(O)=O IFTVANMRTIHKML-WDSKDSINSA-N 0.000 description 2
- OSRZOHXQCUFIQG-FPMFFAJLSA-N Ala-Phe-Pro Chemical compound C([C@H](NC(=O)[C@@H]([NH3+])C)C(=O)N1[C@H](CCC1)C([O-])=O)C1=CC=CC=C1 OSRZOHXQCUFIQG-FPMFFAJLSA-N 0.000 description 2
- ADSGHMXEAZJJNF-DCAQKATOSA-N Ala-Pro-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)N ADSGHMXEAZJJNF-DCAQKATOSA-N 0.000 description 2
- GMGWOTQMUKYZIE-UBHSHLNASA-N Ala-Pro-Phe Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 GMGWOTQMUKYZIE-UBHSHLNASA-N 0.000 description 2
- KJGNDQCYBNBXDA-GUBZILKMSA-N Arg-Arg-Cys Chemical compound C(C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CS)C(=O)O)N)CN=C(N)N KJGNDQCYBNBXDA-GUBZILKMSA-N 0.000 description 2
- BHSYMWWMVRPCPA-CYDGBPFRSA-N Arg-Arg-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CCCN=C(N)N BHSYMWWMVRPCPA-CYDGBPFRSA-N 0.000 description 2
- NGYHSXDNNOFHNE-AVGNSLFASA-N Arg-Pro-Leu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(O)=O NGYHSXDNNOFHNE-AVGNSLFASA-N 0.000 description 2
- PYDIIVKGTBRIEL-SZMVWBNQSA-N Arg-Trp-Pro Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N1CCC[C@H]1C(O)=O PYDIIVKGTBRIEL-SZMVWBNQSA-N 0.000 description 2
- SPIPSJXLZVTXJL-ZLUOBGJFSA-N Asn-Cys-Ser Chemical compound NC(=O)C[C@H](N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CO)C(O)=O SPIPSJXLZVTXJL-ZLUOBGJFSA-N 0.000 description 2
- VHWNKSJHQFZJTH-FXQIFTODSA-N Asp-Asp-Met Chemical compound CSCC[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(=O)O)N VHWNKSJHQFZJTH-FXQIFTODSA-N 0.000 description 2
- SPKCGKRUYKMDHP-GUDRVLHUSA-N Asp-Ile-Pro Chemical compound CC[C@H](C)[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)NC(=O)[C@H](CC(=O)O)N SPKCGKRUYKMDHP-GUDRVLHUSA-N 0.000 description 2
- OEDJQRXNDRUGEU-SRVKXCTJSA-N Asp-Leu-His Chemical compound N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CNC=N1)C(=O)O OEDJQRXNDRUGEU-SRVKXCTJSA-N 0.000 description 2
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WO2024000620A1 (zh) * | 2022-06-27 | 2024-01-04 | 南京华狮新材料有限公司 | 一种固定化酶及其用于制备乙基己基甘油的用途及方法 |
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WO2024000620A1 (zh) * | 2022-06-27 | 2024-01-04 | 南京华狮新材料有限公司 | 一种固定化酶及其用于制备乙基己基甘油的用途及方法 |
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