KR900004711A - 광학 활성-3-페닐글리시드산 에스테르의 제조방법 - Google Patents

광학 활성-3-페닐글리시드산 에스테르의 제조방법 Download PDF

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KR900004711A
KR900004711A KR1019890012612A KR890012612A KR900004711A KR 900004711 A KR900004711 A KR 900004711A KR 1019890012612 A KR1019890012612 A KR 1019890012612A KR 890012612 A KR890012612 A KR 890012612A KR 900004711 A KR900004711 A KR 900004711A
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genus
acid ester
enzyme
optically active
optical symmetry
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KR1019890012612A
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KR960004455B1 (ko
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다께지 시바따니
가쯔히꼬 나까미찌
히로아끼 마쯔마에
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찌바따 이찌로
다나베 세이야꾸 가부시끼 가이샤
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    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction

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  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

내용 없음

Description

광학 활성-3-페닐글리시드 산 에스테르의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 메틸(2R,3S)-3-(4-메톡시페닐)글리시데이트의 IR 흡수 스펙트럼이고;
제2도는 동일 화합물의 NMR 스펙트럼이며;
제3도는 동일 화합물의 질량 스펙트럼이다.

Claims (11)

  1. (a) 에스테르 결합을 입체선택적으로 가수분해시킬 수 있는 효소를 라세미성 3-페닐글리시드 산 에스테르 화합물(Ⅰ)에 작용시킴으로써 이중 하나의 광학 활성 이성테를 입체선택적으로 가수분해시킨 다음, (b) 반응 혼합물로부터 이의 광학대칭체를 수거하고 분리함을 특징으로 하여, 일반식(Ⅰ)의 3-페닐 글리시드 산 에스테르 화합물의 광학활성 이성체를 제조하는 방법.
    상기식에서, 환 A는 치환되거나 비치환된 페닐 그룹이고, R은 에스테르 잔기이다.
  2. 제1항에 있어서, 효소가 에스테라제 또는 리파제인 방법.
  3. 제1항에 있어서, 분리되고 수거된 광학 대칭체의 배위가 (2R,3S)인 방법.
  4. 제1항에 있어서, 분리되고 수거된 광학 대칭체가 저급 알킬 (2R,3S)-3-(4-메톡시페닐)글리시데이트인 방법.
  5. 제1항에 있어서, 분리되고 수거된 광학 대칭체가 메틸 (2R,3S)-3-(4-메톡시페닐)글리시데이트인 방법.
  6. 제1항에 있어서, 입체선택적 가수분해 반응을, 효소를 라세미성 3-페닐 글리시드 산 에스테르 화합물과 용매중에서 접촉시킴으로써 수행하는 방법.
  7. 제2항에 있어서, 상기 효소를 생성시키는 미생물의 배양 육즙, 상기 배양 육즙으로부터 수거된 미생물 세포 또는 상기 미셍물 세포의 가공품을 효소공급원으로서 사용하는 방법.
  8. 제7항에 있어서, 미생물이 압시디아(Absidia)속, 아스퍼질루스(Aspergillus)속, 푸라리움(Fusar-iun)속, 지베렐라(Gibberella)속, 무코르(Mucor)속, 뉴로스포라(Neurospora)속, 라이조푸스(Rhizopus)속, 트라이코더마(Trichoderma)속, 아크로모박터(Achromo-bacter)속, 알칼리겐스(Alcaligenes)속, 바실루스(Bacillus)속, 브레비박테리움(Brevibacterium)속, 코리네박테리움(Corynebacterium)속, 프로비덴시아(Providencia)속, 슈도모나스(Pseudomonas)속, 세라티아(Serratia)속, 칸디다(Candida)속, 사카로마이콥시스(Saccharomycopsis)속 또는 노카디아(Nocardia)속에 속하는 미생물인 방법.
  9. 제6항에 있어서, 기질의 농도가 0.05 내지 20%인 방법.
  10. 제6항에 있어서, 반응을 물 또는 수성용매 및 유기용매의 이상(two-phase)용매 시스템중에서 수행하는 방법.
  11. 제10항에 있어서, 유기용매가 사염화탄소, 클로로포름, 디클로로메탄, 트리클로로에틸렌, 클로로벤젠, 벤젠, 톨루엔, 크실렌, t-부틸 메틸 에테르, 디이소프로필 에테르, 메틸 이소부틸 케톤, 메틸 에틸 케톤, 에틸 아세테이트, 부틸 아세테이트, n-프로필 알코올, 이소프로필 알코올, n-부틸 알코올 및 t-부틸 알코올중에서 선택되는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890012612A 1988-09-02 1989-09-01 광학 활성 3-페닐글리시드산 에스테르의 제조방법 KR960004455B1 (ko)

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JP63-221016 1988-09-02
JP(?)63-221016 1988-09-02
JP22101688 1988-09-02

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KR900004711A true KR900004711A (ko) 1990-04-12
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EP (1) EP0362556B1 (ko)
KR (1) KR960004455B1 (ko)
CN (1) CN1041785A (ko)
AT (1) ATE113661T1 (ko)
AU (1) AU619890B2 (ko)
DE (1) DE68919184T2 (ko)
DK (1) DK173105B1 (ko)
ES (1) ES2065957T3 (ko)
FI (1) FI95931C (ko)
HU (1) HU203581B (ko)
IE (1) IE65881B1 (ko)
IL (1) IL91453A0 (ko)

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US6521445B1 (en) * 1988-10-26 2003-02-18 Sepracor, Inc. Process for preparing optically active glycidate esters
US5274300A (en) 1988-10-26 1993-12-28 Sepracor, Inc. Enzymatic hydrolysis of glycidate esters in the presence of bisulfite anion
DE3927370A1 (de) * 1989-08-19 1991-02-21 Bayer Ag Verfahren zur herstellung von clausenamid und neoclausenamid und deren derivate
JPH088879B2 (ja) * 1989-09-13 1996-01-31 田辺製薬株式会社 光学活性３―フェニルグリシッド酸エステル類化合物の製法
IE75884B1 (en) * 1990-03-13 1997-09-24 Tanabe Seiyaku Co Esterase from serratia and process for preparing the same
JPH0779706B2 (ja) * 1990-03-22 1995-08-30 田辺製薬株式会社 ２―クロロ―３―ヒドロキシ―３―フエニルプロピオン酸エステル類の製法
IT1249777B (it) * 1990-05-17 1995-03-18 Zambon Spa Processo per la preparazione di intermedi per la sintesi del diltiazem
FR2672600B1 (fr) * 1991-02-08 1994-10-14 Synthelabo Procede de preparation du (-)-(2r,3s)-2,3-epoxy-3-(4-methoxyphenyl) propionate de methyle.
FI93833C (fi) * 1992-05-14 1995-06-12 Orion Yhtymae Oy Menetelmä propionihappojohdosten valmistamiseksi
EP0644940A1 (en) * 1992-05-15 1995-03-29 Syntex Pharmaceuticals International Limited PROCESS FOR ENZYMATIC PREPARATION OF -i(S)-6-METHOXY-A-METHYL-2-MAPHTHALENEACETIC ACID
US6020174A (en) * 1992-07-27 2000-02-01 The Board Of Governors For Higher Education Chemoenzymatic synthesis of the taxol C-13 side chain N-benzolyl- (2R,3S)-Phenylisoserine
NL9202208A (nl) * 1992-12-18 1994-07-18 Dsm Nv Werkwijze voor de enzymatische bereiding van optisch aktieve glycidezure esters.
WO1996012035A1 (en) * 1994-10-12 1996-04-25 E.I. Du Pont De Nemours And Company Enzymatic process for the preparation of chiral-alpha-tertiary carboxylic acid esters
US5529929A (en) * 1995-06-07 1996-06-25 Seprachem, Inc. Optical resolution of alkyl 1,4-benzodioxan-2-carboxylates using esterase from serratia marcescens
US5658796A (en) * 1995-06-07 1997-08-19 Seprachem, Inc. Optical resolution of alkyl chroman-2-carboxylates
IL121525A0 (en) * 1996-08-26 1998-02-08 Tanabe Seiyaku Co Process for preparing optically active benzothiazepine compound and intermediate therefor
IL123352A0 (en) 1997-02-27 1998-09-24 Tanabe Seiyaku Co Process for preparing an optically active trans-3-substituted glycidic acid ester
CN1266430A (zh) * 1997-06-11 2000-09-13 田边制药株式会社 制备光学活性的苯基环氧乙烷化合物的方法
US7169944B2 (en) 2002-09-25 2007-01-30 Tosoh Corporation Optically active epoxy compounds and processes for their production
KR100846676B1 (ko) * 2006-04-27 2008-07-16 엔자이텍 주식회사 효소적 방법에 의한 광학활성 2-할로-2-(엔-치환된페닐)아세트산 에스테르와 2-할로-2-(엔-치환된페닐)아세트산의 제조 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585768A (en) * 1984-04-10 1986-04-29 Tanabe Seiyaku Co., Ltd. 1,5-benzothiazepine derivatives and processes for preparing the same
DE3532026A1 (de) * 1985-09-09 1987-03-19 Hoechst Ag Verfahren zur herstellung optisch aktiver (alpha)-phenoxypropionsaeure und deren derivate
IT1189069B (it) * 1986-03-14 1988-01-28 Donegani Guido Ist Processo per la preparazione biotecnologica della l(-)-carnitina cloruro
DE3785132T2 (de) * 1986-04-16 1993-10-21 Sumitomo Chemical Co Herstellung optisch aktiver cyclopropancarbonsäuren.

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DE68919184D1 (de) 1994-12-08
EP0362556A1 (en) 1990-04-11
CN1041785A (zh) 1990-05-02
IL91453A0 (en) 1990-04-29
HU203581B (en) 1991-08-28
ES2065957T3 (es) 1995-03-01
DK434889A (da) 1990-03-03
FI894022A0 (fi) 1989-08-28
AU4097789A (en) 1990-03-08
IE892817L (en) 1990-03-02
DE68919184T2 (de) 1995-04-13
DK173105B1 (da) 2000-01-17
KR960004455B1 (ko) 1996-04-06
DK434889D0 (da) 1989-09-01
EP0362556B1 (en) 1994-11-02
IE65881B1 (en) 1995-11-29
FI894022A (fi) 1990-03-03
AU619890B2 (en) 1992-02-06
FI95931B (fi) 1995-12-29
HUT52162A (en) 1990-06-28
ATE113661T1 (de) 1994-11-15
FI95931C (fi) 1996-04-10

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