CN101560532B - L-茶氨酸酶法转化制备方法 - Google Patents
L-茶氨酸酶法转化制备方法 Download PDFInfo
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- CN101560532B CN101560532B CN2009100271924A CN200910027192A CN101560532B CN 101560532 B CN101560532 B CN 101560532B CN 2009100271924 A CN2009100271924 A CN 2009100271924A CN 200910027192 A CN200910027192 A CN 200910027192A CN 101560532 B CN101560532 B CN 101560532B
- Authority
- CN
- China
- Prior art keywords
- theanine
- glutamic acid
- ethamine
- acid
- reaction
- 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.)
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- DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine Chemical compound CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 title claims abstract description 134
- DATAGRPVKZEWHA-UHFFFAOYSA-N L-gamma-glutamyl-n-ethylamine Natural products CCNC(=O)CCC(N)C(O)=O DATAGRPVKZEWHA-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 230000009466 transformation Effects 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 17
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 14
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 101710107035 Gamma-glutamyltranspeptidase Proteins 0.000 claims abstract description 10
- 101710173228 Glutathione hydrolase proenzyme Proteins 0.000 claims abstract description 10
- 102000006640 gamma-Glutamyltransferase Human genes 0.000 claims abstract description 10
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 5
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 34
- 239000000758 substrate Substances 0.000 claims description 17
- -1 metals ion Chemical class 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 23
- 241000894006 Bacteria Species 0.000 abstract description 12
- 238000002425 crystallisation Methods 0.000 abstract description 10
- 230000008025 crystallization Effects 0.000 abstract description 10
- 102000004190 Enzymes Human genes 0.000 abstract description 9
- 108090000790 Enzymes Proteins 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 125000003338 L-glutaminyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C(=O)N([H])[H] 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000012530 fluid Substances 0.000 description 24
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 16
- 230000006837 decompression Effects 0.000 description 16
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 9
- 239000013612 plasmid Substances 0.000 description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 239000003729 cation exchange resin Substances 0.000 description 8
- 239000010413 mother solution Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
- 239000006228 supernatant Substances 0.000 description 8
- 238000003828 vacuum filtration Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 230000000968 intestinal effect Effects 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 238000010353 genetic engineering Methods 0.000 description 4
- 229920002114 octoxynol-9 Polymers 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229940026510 theanine Drugs 0.000 description 3
- 230000009261 transgenic effect Effects 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DGIMBMZJSZEZJD-ZLELNMGESA-N (2s)-2-amino-5-(ethylamino)-5-oxopentanoic acid Chemical compound CCNC(=O)CC[C@H](N)C(O)=O.CCNC(=O)CC[C@H](N)C(O)=O DGIMBMZJSZEZJD-ZLELNMGESA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000007926 Craterellus fallax Nutrition 0.000 description 1
- 240000007175 Datura inoxia Species 0.000 description 1
- 102000009127 Glutaminase Human genes 0.000 description 1
- 108010073324 Glutaminase Proteins 0.000 description 1
- 101001091385 Homo sapiens Kallikrein-6 Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102100034866 Kallikrein-6 Human genes 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 108020002326 glutamine synthetase Proteins 0.000 description 1
- 102000005396 glutamine synthetase Human genes 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
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CN101560532A CN101560532A (zh) | 2009-10-21 |
CN101560532B true CN101560532B (zh) | 2012-11-14 |
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Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102181501B (zh) * | 2011-03-18 | 2013-01-02 | 南京工业大学 | 一种酶法合成l-茶氨酸的方法 |
CN102295574B (zh) * | 2011-08-08 | 2014-03-26 | 四川同晟氨基酸有限公司 | 合成茶氨酸的方法 |
CN106916858B (zh) * | 2017-03-28 | 2020-10-09 | 宿州学院 | 一种γ-L-谷氨酰正丁胺的酶法转化制备方法 |
CN107828754B (zh) * | 2017-12-13 | 2020-08-04 | 江南大学 | 一种酶活提高的γ-谷氨酰转肽酶突变体及其构建方法 |
CN110564789B (zh) * | 2019-09-12 | 2021-05-04 | 河南巨龙生物工程股份有限公司 | 一种利用大肠杆菌发酵生产l-茶氨酸的方法 |
CN111073830B (zh) * | 2019-11-29 | 2021-07-23 | 河南巨龙生物工程股份有限公司 | 一株高产γ-谷氨酰转肽酶的干酪乳杆菌及其在L-茶氨酸生产中的应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004016798A1 (ja) * | 2002-08-06 | 2004-02-26 | Taiyokagaku Co.,Ltd. | テアニンの製造法 |
CN101270376A (zh) * | 2008-05-14 | 2008-09-24 | 南京工业大学 | 一种酶法合成l-茶氨酸的方法 |
CN101343618A (zh) * | 2008-08-19 | 2009-01-14 | 江南大学 | 天然茶氨酸的制备方法 |
-
2009
- 2009-05-25 CN CN2009100271924A patent/CN101560532B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004016798A1 (ja) * | 2002-08-06 | 2004-02-26 | Taiyokagaku Co.,Ltd. | テアニンの製造法 |
CN101270376A (zh) * | 2008-05-14 | 2008-09-24 | 南京工业大学 | 一种酶法合成l-茶氨酸的方法 |
CN101343618A (zh) * | 2008-08-19 | 2009-01-14 | 江南大学 | 天然茶氨酸的制备方法 |
Non-Patent Citations (2)
Title |
---|
中试规模制备L-茶氨酸及其衍生物;钱绍松等;《精细化工》;20051130;第22卷(第11期);全文 * |
钱绍松等.中试规模制备L-茶氨酸及其衍生物.《精细化工》.2005,第22卷(第11期),全文. |
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Correction item: Description Correct: Increasing embodiments 1 and 2 False: Lack of embodiments 1 and 2 Number: 42 Volume: 25 |
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Effective date of registration: 20121221 Address after: 324400 Zhejiang province Longyou County Chengnan Industrial Zone Industrial Road No. 12 Patentee after: ZHEJIANG TIANRUI CHEMICAL Co.,Ltd. Address before: 210097 Hankou Road, Jiangsu city of Nanjing province No. 22 Patentee before: Nanjing University |
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Denomination of invention: Preparation method for enzymatic conversion of L-theanine Effective date of registration: 20231108 Granted publication date: 20121114 Pledgee: China Construction Bank Corporation Longyou Branch Pledgor: ZHEJIANG TIANRUI CHEMICAL Co.,Ltd. Registration number: Y2023980064602 |
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