KR970043060A - 포스파티딜세린의 제조방법 - Google Patents
포스파티딜세린의 제조방법 Download PDFInfo
- Publication number
- KR970043060A KR970043060A KR1019960062864A KR19960062864A KR970043060A KR 970043060 A KR970043060 A KR 970043060A KR 1019960062864 A KR1019960062864 A KR 1019960062864A KR 19960062864 A KR19960062864 A KR 19960062864A KR 970043060 A KR970043060 A KR 970043060A
- Authority
- KR
- South Korea
- Prior art keywords
- serine
- phospholipid
- acid
- phase
- salts
- Prior art date
Links
- 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 4
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 title claims 18
- 150000003904 phospholipids Chemical class 0.000 claims abstract 8
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract 3
- 206010027476 Metastases Diseases 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 230000009401 metastasis Effects 0.000 claims abstract 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 9
- 229960001153 serine Drugs 0.000 claims 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 239000012071 phase Substances 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000012074 organic phase Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 239000005642 Oleic acid Substances 0.000 claims 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 2
- 102000003867 Phospholipid Transfer Proteins Human genes 0.000 claims 2
- 108090000216 Phospholipid Transfer Proteins Proteins 0.000 claims 2
- 235000021355 Stearic acid Nutrition 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- -1 alkali metal salt Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- 235000021313 oleic acid Nutrition 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000008117 stearic acid Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000004381 Choline salt Substances 0.000 claims 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021319 Palmitoleic acid Nutrition 0.000 claims 1
- 102000011420 Phospholipase D Human genes 0.000 claims 1
- 108090000553 Phospholipase D Proteins 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- 235000021342 arachidonic acid Nutrition 0.000 claims 1
- 235000019417 choline salt Nutrition 0.000 claims 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000008344 egg yolk phospholipid Substances 0.000 claims 1
- 238000000909 electrodialysis Methods 0.000 claims 1
- 238000000855 fermentation Methods 0.000 claims 1
- 230000004151 fermentation Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 229940067606 lecithin Drugs 0.000 claims 1
- 235000010445 lecithin Nutrition 0.000 claims 1
- 239000000787 lecithin Substances 0.000 claims 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229940083466 soybean lecithin Drugs 0.000 claims 1
- 239000008347 soybean phospholipid Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229940042880 natural phospholipid Drugs 0.000 abstract 1
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
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
본 발명은 수상/유기상의 2상계에서 인지질전이활성을 갖는 포스포리파아제 D의 존재하에서, 라세미체 혹은 거울상 이성질적으로 순수한 세린, 바람직하기로는 (L)세린을, 콩이나 달걀의 레시틴과 같은 천연 인지질과 반응시키거나, 합성 인지질과 반응시킴으로써 포스파티딜 세린을 제조하는 방법에 관한 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 하기 화학식 1로 표시되는 화합물의 제조방법에 있어서, 상기 방법이 수상/유기상의 2상계에서 높은 인지질전이활성을 갖는 세포이 포스포리파아제 D (PLD)를 생산하는 미생물균주의 발효배양액을 언심분리시켜 얻은 미정제된 PLD의 존재하에서 하기 화학식 2로 표시되는 인지질을 라세미체 혹은 거울상이성질적으로 순수한 세린, 바람직하기로는 L-세린과 반응시키는 단계를 포함하는 방법.여기서 R1과 R2는 같거나 다를 수 있으며, C10 -C30아실로서 경우에 따라 불포화결합을 하나 또는 복수개 가지고 있으며 ; X는 OH 또는 OM (여기서 M은 알칼리금속, 알칼리토금속, 내부에 염을 포함하는 암모늄이나 알킬암모늄이다)이고; R3는 CH2CH2NH2또는 CH2CH2N+(CH3)|3이다.
- 제1항에 있어서, 상기 유기용매가 톨루엔인 것을 특징으로 하는 제조방법.
- 제1항에 있어서, 화학식2로 표시되는 상기 인지질이 인지질함량 20% 내지 95%인 콩의 레시틴 또는 달걀의 레시틴으로부터 추출된 천연의 포스타티딜콜린 및/또는 포스타티딜에탄올아민의 혼합물인 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 반응 pH가 4 내지 4.5인 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 반응온도가 25℃±5℃인 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 미정제된 포스포리파아제 D가 스트렙토마이세스 균주 ATCC 55717로부터 제조된 것임을 특징으로 하는 제조방법.
- 제1항에 있어서, 상기 R1과 R2가팔미틴산, 스테아린산, 올레인산, 리놀산 또는 리놀레인산의 아실사슬로서 그 비율이 콩의 레시틴과 비슷한 포스파티달-(L)-세린을 제조하는 것을 특징으로 하는 제조방법.
- 제1항에 있어서, 상기 R1과 R2가 팔미틴산, 스테아린산, 팔미톨레인산, 올레인산, 리놀레인산, 아라키돈산의 아실사슬로서 그 비율이 달걀의 레시틴과 비슷한 포스파티딜-(L)-세린을 제조하는 것을 특징으로 하는 제조방법.
- 알칼리금속염, 알칼리토금속염, 암모늄염 또는 알킬암모늄염의 형태인 포스파티딜세린을 정제하는 방법으로서, 2상의 유기용매계에서 PS를 포함한 인지질 혼합물을 선택적으로 추출하는 것을 특징으로 하는 제조방법.
- 제9항에 있어서, 상기 포스파티딜세린을 헵탄/메탄을 혼합물로부터 대응하는 칼슘염을 선택적으로 추출함으로써 다른 인지질, 특히 PC, PE, PA 및 대응하는 라이소인지질로부터 정제하는 것을 특징으로 하는 제조방법.
- 제10항에 의해 얻어진 PS를 더욱 정제하는 방법에 있어서, 헵탄/아세톤으로부터 칼슘염형태로 결정화한 다음, 기타 다른 염으로 전환시키는 것을 특징으로 하는 제조방법.
- 제1항의 인지질전이반응 용액으로부터 L-세린을 결정형고체로 회수하는 방법에 있어서, 상기 방법이 유기상의 분리가 끝난 후에 상기 수상을 진공하에서 부분적으로 농축하여 결정형 L-세린으로 침전시키는 것을 특징으로 하는 회수방법.
- 제1항의 인지질전이반응 용액으로부터 L-세린을 무기염 및 콜린염이 제거된 수용액 형태로 회수하는 방법에 있어서, 상기 방법이 상기 유기상을 여과 및 분리한후 상기 수상을 이온교환수지로 처리하거나, pH 5.7±0.5에서 전기투석하는 것을 특징으로 하는 회수방법.
- 미국균주기탁기관 (American Type Culture Collection (ATCC))에 기탁번호 55717 (1995년 10월 13일자)로 기탁된 스트랩토마이세스.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US570,000 | 1995-12-08 | ||
| US08/570,000 US5700668A (en) | 1995-12-08 | 1995-12-08 | Process for the industrial preparation of phosphatidylserine |
| US08//570,000 | 1995-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR970043060A true KR970043060A (ko) | 1997-07-26 |
| KR100446399B1 KR100446399B1 (ko) | 2004-11-12 |
Family
ID=24277783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960062864A KR100446399B1 (ko) | 1995-12-08 | 1996-12-07 | 포스파티딜세린의제조방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5700668A (ko) |
| EP (2) | EP0776976B2 (ko) |
| JP (1) | JPH09173092A (ko) |
| KR (1) | KR100446399B1 (ko) |
| AT (2) | ATE203057T1 (ko) |
| CA (1) | CA2192257A1 (ko) |
| DE (3) | DE776976T1 (ko) |
| ES (2) | ES2105999T5 (ko) |
| IT (1) | IT1316435B1 (ko) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3791951B2 (ja) * | 1995-11-08 | 2006-06-28 | 株式会社ヤクルト本社 | 多価不飽和脂肪酸含有ホスファチジルセリンを含む油脂組成物の製造方法 |
| JP4331896B2 (ja) * | 1998-03-31 | 2009-09-16 | タカラバイオ株式会社 | リゾスフィンゴ脂質の製造方法 |
| WO2000018945A1 (en) * | 1998-10-01 | 2000-04-06 | Albany Molecular Research, Inc. | Transphosphatidylation catalized by phospholipase d in anhydrous organic solvents in the presence of ion-exchange resin |
| DE19917249C2 (de) * | 1999-02-26 | 2001-09-27 | Meyer Lucas Gmbh & Co | Verfahren zur Herstellung von Phosphatidylserin-Produkten |
| IT1311929B1 (it) * | 1999-04-28 | 2002-03-20 | Chemi Spa | Procedimento per la preparazione di fosfatidilserine. |
| IL139224A (en) * | 2000-10-23 | 2009-09-01 | David Rutenberg | Anti depressant, stress suppressor and mood improver |
| IT1319679B1 (it) * | 2000-12-05 | 2003-10-23 | Chemi Spa | Processo di purificazione di fosfatidilserina. |
| JP3697189B2 (ja) * | 2001-01-11 | 2005-09-21 | 日清オイリオグループ株式会社 | リン脂質の塩基交換方法 |
| ITPD20010031A1 (it) * | 2001-02-09 | 2002-08-09 | Fidia Farmaceutici | Procedimento per la preparazione di fosfatidi puri e loro impiego in campo cosmetico, farmaceutico ed alimentare. |
| US6635456B2 (en) | 2001-02-09 | 2003-10-21 | Fidia Farmaceutici S.P.A. | Procedure for the preparation of pure phosphatides with phospholipase D |
| KR100442538B1 (ko) * | 2001-05-07 | 2004-07-30 | 주식회사 두산 | 유기용매에서 포스파티딜세린 및 리조포스파티딜세린의제조방법 |
| KR20030086128A (ko) * | 2002-05-03 | 2003-11-07 | 주식회사 두산 | 효소 및 세린의 재사용을 포함하는 포스파티딜세린 및리소포스파티딜세린의 제조방법 |
| KR20040069438A (ko) * | 2003-01-29 | 2004-08-06 | 주식회사 두산 | 유기용매 혼합물을 이용한 변형 레시틴의 제조방법 |
| US6878532B1 (en) | 2003-04-28 | 2005-04-12 | Sioux Biochemical, Inc. | Method of producing phosphatidylserine |
| IL158139A0 (en) * | 2003-09-25 | 2004-09-27 | Enzymotec Ltd | Stabilized formulations of phosphatidyl serine |
| JP4891522B2 (ja) * | 2003-10-03 | 2012-03-07 | 株式会社ファンケル | 血清ｇｏｔ、ｇｐｔ改善剤 |
| US7935365B2 (en) * | 2003-10-22 | 2011-05-03 | Enzymotec, Ltd. | Glycerophospholipids for the improvement of cognitive functions |
| US20050130937A1 (en) * | 2003-10-22 | 2005-06-16 | Enzymotec Ltd. | Lipids containing omega-3 and omega-6 fatty acids |
| US8052992B2 (en) * | 2003-10-22 | 2011-11-08 | Enzymotec Ltd. | Glycerophospholipids containing omega-3 and omega-6 fatty acids and their use in the treatment and improvement of cognitive functions |
| DE102004002053A1 (de) * | 2004-01-15 | 2005-08-04 | Bioghurt Biogarde Gmbh & Co. Kg | Verfahren zur Herstellung von Phosphatidylserin und dessen Reinigung durch Extraktion |
| JP2005318827A (ja) * | 2004-05-07 | 2005-11-17 | Nisshin Oillio Group Ltd | セリンの回収方法 |
| CN1308334C (zh) * | 2004-06-01 | 2007-04-04 | 山东师范大学 | 一种从动物脑提取磷脂酰丝氨酸的方法 |
| DE102004038443A1 (de) * | 2004-08-07 | 2006-03-16 | Bioghurt Biogarde Gmbh & Co. Kg | Verfahren zur enzymatischen Herstellung und/oder Modifikation von Phospholipiden |
| CN1305882C (zh) * | 2005-04-30 | 2007-03-21 | 海城后英生物工程有限公司 | 大豆卵磷脂的加工工艺 |
| ITPD20050164A1 (it) | 2005-05-30 | 2006-11-30 | Fidia Farmaceutici | Processo per la preparazione e l'isolamento di fosfatidi |
| RU2482186C2 (ru) * | 2008-05-15 | 2013-05-20 | Лодерс Кроклан Б.В. | Способ получения фосфатидилсерина |
| US8846338B2 (en) * | 2008-08-07 | 2014-09-30 | Lipogen Ltd. | Processes for the preparation of phosphatides |
| JP2012087203A (ja) * | 2010-10-19 | 2012-05-10 | Honda Denki Kk | セラミドの製造方法及びそれに用いる金属除去装置 |
| ITPD20120021A1 (it) | 2012-01-26 | 2013-07-27 | Fidia Farmaceutici | "nuove composizioni farmaceutiche contenenti fosfatidilserina e curcumina". |
| CN103351403A (zh) * | 2013-07-24 | 2013-10-16 | 华东师范大学 | 一种磷脂酰丝氨酸的合成方法 |
| WO2016012861A1 (en) | 2014-07-25 | 2016-01-28 | Enzymotec Ltd. | Nutritional compositions containing phosphatidylserine powder |
| US20190015435A1 (en) * | 2016-01-21 | 2019-01-17 | Enzymotec Ltd. | Methods using phosphatidylserine powder |
| CN116173045A (zh) * | 2022-09-21 | 2023-05-30 | 中国医学科学院基础医学研究所 | 甘油磷脂类化合物在预防和治疗高血脂、动脉粥样硬化、非酒精性脂肪肝和肥胖中的用途 |
| CN116391876A (zh) * | 2023-05-22 | 2023-07-07 | 陕西中科通大生命科学技术有限公司 | 一种改性磷脂酰丝氨酸口服制剂的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2651646A (en) † | 1950-03-04 | 1953-09-08 | Colgate Palmolive Peet Co | Liquid-liquid extraction process |
| US3436413A (en) † | 1965-12-21 | 1969-04-01 | Canada Packers Ltd | Process for the isolation of phosphatidyl serine |
| JPS5743781A (en) | 1980-08-29 | 1982-03-11 | Janome Sewing Machine Co Ltd | Elongator device for electronic sewing machine |
| GR74979B (ko) † | 1980-10-02 | 1984-07-12 | Unilever Nv | |
| US5084215A (en) * | 1984-02-13 | 1992-01-28 | The Liposome Company, Inc. | Process for purification of phospholipids |
| JPS6336791A (ja) | 1986-08-01 | 1988-02-17 | Nippon Oil & Fats Co Ltd | 酵素によるリン脂質の製造方法 |
| JPH0716426B2 (ja) † | 1986-08-01 | 1995-03-01 | 日本油脂株式会社 | 酵素によるリン脂質の製造方法 |
| DE3627079C1 (de) † | 1986-08-09 | 1987-10-08 | Heidenhain Gmbh Dr Johannes | Laengenmesseinrichtung |
| JPH0761276B2 (ja) † | 1986-11-14 | 1995-07-05 | 名糖産業株式会社 | 酵素法リン脂質−ｄ−セリン誘導体の製造法 |
| JPH0279990A (ja) * | 1988-09-16 | 1990-03-20 | Nippon Oil & Fats Co Ltd | ホスファチジルセリンの製造方法 |
| JPH05336983A (ja) † | 1992-06-04 | 1993-12-21 | Kanegafuchi Chem Ind Co Ltd | リン脂質の生産方法 |
-
1995
- 1995-12-08 US US08/570,000 patent/US5700668A/en not_active Expired - Lifetime
-
1996
- 1996-08-02 IT IT1996MI001686A patent/IT1316435B1/it active
- 1996-12-03 EP EP96119350.5A patent/EP0776976B2/en not_active Expired - Lifetime
- 1996-12-03 ES ES96119350.5T patent/ES2105999T5/es not_active Expired - Lifetime
- 1996-12-03 EP EP98111111A patent/EP0922707B2/en not_active Expired - Lifetime
- 1996-12-03 AT AT96119350T patent/ATE203057T1/de not_active IP Right Cessation
- 1996-12-03 DE DE0776976T patent/DE776976T1/de active Pending
- 1996-12-03 DE DE69613801.8T patent/DE69613801T3/de not_active Expired - Lifetime
- 1996-12-03 AT AT98111111T patent/ATE208399T1/de not_active IP Right Cessation
- 1996-12-03 ES ES98111111T patent/ES2165115T5/es not_active Expired - Lifetime
- 1996-12-03 DE DE69616834T patent/DE69616834T3/de not_active Expired - Lifetime
- 1996-12-06 CA CA002192257A patent/CA2192257A1/en not_active Abandoned
- 1996-12-06 JP JP8326787A patent/JPH09173092A/ja active Pending
- 1996-12-07 KR KR1019960062864A patent/KR100446399B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0776976A2 (en) | 1997-06-04 |
| EP0922707B1 (en) | 2001-11-07 |
| DE69616834T3 (de) | 2010-07-01 |
| US5700668A (en) | 1997-12-23 |
| EP0776976B1 (en) | 2001-07-11 |
| DE69616834D1 (de) | 2001-12-13 |
| IT1316435B1 (it) | 2003-04-22 |
| ITMI961686A1 (it) | 1998-02-02 |
| ES2105999T1 (es) | 1997-11-01 |
| KR100446399B1 (ko) | 2004-11-12 |
| ATE203057T1 (de) | 2001-07-15 |
| DE69613801T2 (de) | 2001-11-22 |
| ES2105999T5 (es) | 2014-12-01 |
| DE776976T1 (de) | 1998-02-19 |
| EP0922707B2 (en) | 2009-11-18 |
| JPH09173092A (ja) | 1997-07-08 |
| EP0922707A1 (en) | 1999-06-16 |
| EP0776976B2 (en) | 2014-07-30 |
| DE69613801T3 (de) | 2014-12-18 |
| DE69613801D1 (de) | 2001-08-16 |
| ITMI961686A0 (ko) | 1996-08-02 |
| ES2105999T3 (es) | 2001-09-16 |
| ES2165115T5 (es) | 2010-03-25 |
| ES2165115T3 (es) | 2002-03-01 |
| ATE208399T1 (de) | 2001-11-15 |
| DE69616834T2 (de) | 2002-06-06 |
| CA2192257A1 (en) | 1997-06-09 |
| EP0776976A3 (en) | 1997-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR970043060A (ko) | 포스파티딜세린의 제조방법 | |
| Eibl et al. | [53] Preparation of phospholipids and their analogs by phospholipase D | |
| US6492146B1 (en) | Process for the preparation of phosphatidylserines | |
| EP0819760B1 (en) | Process for producing phosphatidylserines having polybasic unsaturated fatty acid as side chain | |
| US7067292B2 (en) | Method for the production of phospholipids | |
| CH629179A5 (it) | Procedimento per l'idrolisi di idantoine in derivati di d, l amminoacidi. | |
| KR20020058956A (ko) | 엘-라이신의 제조방법 | |
| RU2748950C1 (ru) | Способ извлечения фосфорной кислоты из ферментационного бульона или жидких отходов ферментации и её повторного применения | |
| RU2226550C2 (ru) | Способ ферментативного получения непротеиногенных l-аминокислот | |
| US7049107B1 (en) | Method of producing phosphatidylserine | |
| CA2167186C (en) | Method for precipitating natural avermectins | |
| KR100225669B1 (ko) | 효소를 이용한 고순도 인지질의 생산방법 | |
| JP4081794B2 (ja) | 新規なラビリンチュラ科微生物及びそれを用いた４，７，１０，１３，１６‐ドコサペンタエン酸の製造方法 | |
| CN108315367B (zh) | 一种两步酶解法生产磷酸肌酸的方法 | |
| CA1319123C (en) | Method for the production of (-) 2-substituted-ornithines | |
| US5217886A (en) | Method for the production of (-)-4-difluoromethyl-ornithine | |
| SU839258A1 (ru) | Способ получени липидов | |
| US8377662B2 (en) | Process for the production of N-acyl-phosphatidyl-ethanolamine | |
| US20050250189A1 (en) | Process for recovering serine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20130808 Year of fee payment: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20140806 Year of fee payment: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20150805 Year of fee payment: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20160808 Year of fee payment: 13 |
|
| EXPY | Expiration of term |