CN109486790A - 一种以磷脂酶d转化制备磷酯酰丝氨酸的方法 - Google Patents
一种以磷脂酶d转化制备磷酯酰丝氨酸的方法 Download PDFInfo
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- CN109486790A CN109486790A CN201811503284.0A CN201811503284A CN109486790A CN 109486790 A CN109486790 A CN 109486790A CN 201811503284 A CN201811503284 A CN 201811503284A CN 109486790 A CN109486790 A CN 109486790A
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- serine
- phospholipase
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- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 title claims abstract description 53
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 26
- 102000011420 Phospholipase D Human genes 0.000 title claims abstract description 18
- 108090000553 Phospholipase D Proteins 0.000 title claims abstract description 18
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims abstract description 51
- 239000000758 substrate Substances 0.000 claims abstract description 25
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000035484 reaction time Effects 0.000 claims abstract description 10
- -1 salt ion Chemical class 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 9
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 235000002639 sodium chloride Nutrition 0.000 claims description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 9
- 239000001110 calcium chloride Substances 0.000 claims description 9
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000011592 zinc chloride Substances 0.000 claims description 5
- 235000005074 zinc chloride Nutrition 0.000 claims description 5
- 230000036541 health Effects 0.000 claims description 3
- 235000016709 nutrition Nutrition 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 235000011148 calcium chloride Nutrition 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 235000011147 magnesium chloride Nutrition 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000013618 yogurt Nutrition 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 20
- 108090000790 Enzymes Proteins 0.000 abstract description 20
- 238000005457 optimization Methods 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 108010000126 Gabolysat PC60 Proteins 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007974 sodium acetate buffer Substances 0.000 description 7
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 230000001131 transforming effect Effects 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
-
- 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
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6481—Phosphoglycerides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/04—Phosphoric diester hydrolases (3.1.4)
- C12Y301/04004—Phospholipase D (3.1.4.4)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Description
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CN201811503284.0A CN109486790B (zh) | 2018-12-10 | 2018-12-10 | 一种以磷脂酶d转化制备磷酯酰丝氨酸的方法 |
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CN201811503284.0A CN109486790B (zh) | 2018-12-10 | 2018-12-10 | 一种以磷脂酶d转化制备磷酯酰丝氨酸的方法 |
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CN109486790A true CN109486790A (zh) | 2019-03-19 |
CN109486790B CN109486790B (zh) | 2021-08-03 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111778295A (zh) * | 2019-04-04 | 2020-10-16 | 南通厚元生物科技有限公司 | 一种用固定化生物催化剂合成磷脂酰丝氨酸的方法 |
CN114854801A (zh) * | 2022-05-18 | 2022-08-05 | 翁源广业清怡食品科技有限公司 | 一种无有机溶剂制备磷脂酰丝氨酸的方法 |
Citations (14)
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US6492146B1 (en) * | 1999-04-28 | 2002-12-10 | Chemi S.P.A. | Process for the preparation of phosphatidylserines |
US20040086905A1 (en) * | 2001-02-06 | 2004-05-06 | Debopriya Das | Lipid-associated molecules |
WO2005068644A1 (de) * | 2004-01-15 | 2005-07-28 | Degussa Ag | Verfahren zur herstellung von phosphatidylserin und dessen reinigung durch extraktion |
WO2012071768A1 (zh) * | 2010-12-03 | 2012-06-07 | Zhang Yongzhi | 一种制备富含多不饱和双键脂肪酰基的磷脂酰丝氨酸的高品质南极磷虾油的方法 |
CN102676600A (zh) * | 2012-04-28 | 2012-09-19 | 国家粮食局科学研究院 | 一种制备磷脂酰丝氨酸的方法 |
CN103555783A (zh) * | 2013-10-24 | 2014-02-05 | 陕西源邦生物技术有限公司 | 一种制备磷脂酰丝氨酸的方法 |
US20140099354A1 (en) * | 2011-06-06 | 2014-04-10 | Ulrich Dietz | Biopassivating membrane stabilization by means of nitrocarboxylic acid-containing phospholipids in preparations and coatings |
CN104004797A (zh) * | 2014-06-20 | 2014-08-27 | 天津科技大学 | sn-2位为二十二碳六烯酸的磷脂酰丝氨酸的制备方法 |
CN105087700A (zh) * | 2015-08-31 | 2015-11-25 | 上海裕兰生物科技有限公司 | 高含量磷脂酰丝氨酸的制备方法 |
CN105296560A (zh) * | 2015-12-07 | 2016-02-03 | 杏辉天力(杭州)药业有限公司 | 一种磷脂酰丝氨酸的制备方法 |
CN107164397A (zh) * | 2017-04-28 | 2017-09-15 | 江南大学 | 一种磷脂酶d的基因挖掘及其应用方法 |
CN107722051A (zh) * | 2017-08-24 | 2018-02-23 | 南通励成生物工程有限公司 | 制备磷脂酰丝氨酸盐的方法 |
CN110156829A (zh) * | 2018-02-11 | 2019-08-23 | 浙江医药股份有限公司新昌制药厂 | 高含量磷脂酰丝氨酸的纯化方法 |
CN110938090A (zh) * | 2019-12-24 | 2020-03-31 | 南通励成生物工程有限公司 | 一种磷脂酰丝氨酸的纯化方法 |
-
2018
- 2018-12-10 CN CN201811503284.0A patent/CN109486790B/zh active Active
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US6492146B1 (en) * | 1999-04-28 | 2002-12-10 | Chemi S.P.A. | Process for the preparation of phosphatidylserines |
US20040086905A1 (en) * | 2001-02-06 | 2004-05-06 | Debopriya Das | Lipid-associated molecules |
WO2005068644A1 (de) * | 2004-01-15 | 2005-07-28 | Degussa Ag | Verfahren zur herstellung von phosphatidylserin und dessen reinigung durch extraktion |
WO2012071768A1 (zh) * | 2010-12-03 | 2012-06-07 | Zhang Yongzhi | 一种制备富含多不饱和双键脂肪酰基的磷脂酰丝氨酸的高品质南极磷虾油的方法 |
US20140099354A1 (en) * | 2011-06-06 | 2014-04-10 | Ulrich Dietz | Biopassivating membrane stabilization by means of nitrocarboxylic acid-containing phospholipids in preparations and coatings |
CN102676600A (zh) * | 2012-04-28 | 2012-09-19 | 国家粮食局科学研究院 | 一种制备磷脂酰丝氨酸的方法 |
CN103555783A (zh) * | 2013-10-24 | 2014-02-05 | 陕西源邦生物技术有限公司 | 一种制备磷脂酰丝氨酸的方法 |
CN104004797A (zh) * | 2014-06-20 | 2014-08-27 | 天津科技大学 | sn-2位为二十二碳六烯酸的磷脂酰丝氨酸的制备方法 |
CN105087700A (zh) * | 2015-08-31 | 2015-11-25 | 上海裕兰生物科技有限公司 | 高含量磷脂酰丝氨酸的制备方法 |
CN105296560A (zh) * | 2015-12-07 | 2016-02-03 | 杏辉天力(杭州)药业有限公司 | 一种磷脂酰丝氨酸的制备方法 |
CN107164397A (zh) * | 2017-04-28 | 2017-09-15 | 江南大学 | 一种磷脂酶d的基因挖掘及其应用方法 |
CN107722051A (zh) * | 2017-08-24 | 2018-02-23 | 南通励成生物工程有限公司 | 制备磷脂酰丝氨酸盐的方法 |
CN110156829A (zh) * | 2018-02-11 | 2019-08-23 | 浙江医药股份有限公司新昌制药厂 | 高含量磷脂酰丝氨酸的纯化方法 |
CN110938090A (zh) * | 2019-12-24 | 2020-03-31 | 南通励成生物工程有限公司 | 一种磷脂酰丝氨酸的纯化方法 |
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Title |
---|
TINGTING HUANG等: "Combinatorial Fine-Tuning of Phospholipase D Expression by Bacillus subtilis WB600 for the Production of Phosphatidylserine", 《J. MICROBIOL. BIOTECHNOL.》 * |
YIHAN LIU等: "A novel process for phosphatidylserine production using a Pichia pastoris whole-cell biocatalyst with overexpression of phospholipase D from Streptomyces halstedii in a purely aqueous system", 《FOOD CHEMISTRY》 * |
杜阳吉: "磷脂酶D单一水相法催化合成磷脂酰丝氨酸工艺研究", 《中国食品添加剂》 * |
韩海霞: "磷脂酶D的制备及其在磷脂酰丝氨酸合成中的应用", 《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑》 * |
黄婷婷: "磷脂酶D的重组优化表达及生物转化制备磷脂酰丝氨酸", 《中国优秀硕士学位论文全文数据库基础科学辑》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111778295A (zh) * | 2019-04-04 | 2020-10-16 | 南通厚元生物科技有限公司 | 一种用固定化生物催化剂合成磷脂酰丝氨酸的方法 |
CN114854801A (zh) * | 2022-05-18 | 2022-08-05 | 翁源广业清怡食品科技有限公司 | 一种无有机溶剂制备磷脂酰丝氨酸的方法 |
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