WO1998049339A1 - Procede de production de composes optiquement actifs - Google Patents

Procede de production de composes optiquement actifs Download PDF

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Publication number
WO1998049339A1
WO1998049339A1 PCT/JP1998/001963 JP9801963W WO9849339A1 WO 1998049339 A1 WO1998049339 A1 WO 1998049339A1 JP 9801963 W JP9801963 W JP 9801963W WO 9849339 A1 WO9849339 A1 WO 9849339A1
Authority
WO
WIPO (PCT)
Prior art keywords
ester
alcohol
optically active
lipase
group
Prior art date
Application number
PCT/JP1998/001963
Other languages
English (en)
Japanese (ja)
Inventor
Kaoru Nakamura
Keishi Takenaka
Atsuyoshi Ohno
Yoshiro Furukawa
Original Assignee
Daiso Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Daiso Co., Ltd. filed Critical Daiso Co., Ltd.
Priority to JP54683098A priority Critical patent/JP3550688B2/ja
Publication of WO1998049339A1 publication Critical patent/WO1998049339A1/fr

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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
    • 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

Definitions

  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which may have a substituent, or R 2 represents a substituent.
  • the present invention also provides an ester of [R, S) alkyne alcohol [ ⁇ ] in water or a mixed solvent of water and an organic solvent in the presence of the lipase and polyphenols. Reacts with water to form one optically active alkyne alcohol [II] by the hydrolysis reaction, while leaving the ester [ ⁇ ] of the other optically active alkyne alcohol (R, S) Provided is an optical resolution method for ester [ ⁇ ].
  • the second method is represented by the following reaction formula.
  • Examples of carriers for immobilizing lipase include polymers such as polystyrene, polypropylen, starch, and gluten, activated carbon, porous glass, cerite, zeolite, and the like. Inorganic materials such as iron ore, bentonite, alumina, silica gel, hydroxyapatite, calcium phosphate and metal oxides are exemplified. Carry and fix by the physical adsorption method. The immobilized lipase retains sufficient activity and stereoselectivity of the reaction after completion of the reaction and after recovery from the reaction solution, so that it can be reused repeatedly.
  • Lipase AK Three Lipase AK, lipase P, lipase CES, and rhino from Schdomonas sepacia.
  • Examples include Lase PS, lipase (both from Amano Pharmaceutical Co., Ltd.), and lipase MY (Meito Sangyo Co., Ltd.) derived from Candida silyline lace.
  • reaction rate had reached 55.3%.
  • an S-isomer ester remained in the reaction solution, and its optical purity was 80.0% e e.
  • an R-form alcohol was formed in the reaction solution, and its optical purity was 64.0% e e.
  • optically active alkyne alcohols and esters thereof obtained by the method of the present invention are important as synthetic raw materials or synthetic intermediates of optically active compounds such as drugs, aba drugs, and physiologically active substances.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé qui permet de synthétiser de grandes quantités d'alcynylalcools ayant une pureté optique élevée par des étapes simples avec un catalyseur relativement bon marché. On fait réagir un ester d'alcynylalcool (R, S) (I) avec un alcool en présence d'une lipase capable d'alcooliser stéréosélectivement l'ester sous forme R ou S dans un solvant organique à base d'éther. Il se forme ainsi un alcynylalcool optiquement actif (II), tandis que l'autre ester d'alcynylalcool optiquement actif (III) reste. Dans les formules, R1 représente H ou alkyle C¿1?-C6, et R?3¿ représente alkyle C¿6?-C12.
PCT/JP1998/001963 1997-04-30 1998-04-30 Procede de production de composes optiquement actifs WO1998049339A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP54683098A JP3550688B2 (ja) 1997-04-30 1998-04-30 光学活性化合物の製造法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP11240997 1997-04-30
JP9/112409 1997-04-30
JP7748498 1998-03-25
JP10/77484 1998-03-25

Publications (1)

Publication Number Publication Date
WO1998049339A1 true WO1998049339A1 (fr) 1998-11-05

Family

ID=26418556

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/001963 WO1998049339A1 (fr) 1997-04-30 1998-04-30 Procede de production de composes optiquement actifs

Country Status (2)

Country Link
JP (1) JP3550688B2 (fr)
WO (1) WO1998049339A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002057411A2 (fr) * 2000-12-01 2002-07-25 Diversa Corporation Enzymes hydrolase et utilisation de ceux-ci dans la resolution cinetique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03201996A (ja) * 1989-12-29 1991-09-03 Lion Corp 生化学的手法による光学活性第２級アルキンアルコールの製造法
JPH07233109A (ja) * 1994-02-24 1995-09-05 Sumitomo Chem Co Ltd 光学活性なアルコール誘導体およびその製造法
JPH09107989A (ja) * 1995-10-19 1997-04-28 Daiso Co Ltd 光学活性化合物の製造法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03201996A (ja) * 1989-12-29 1991-09-03 Lion Corp 生化学的手法による光学活性第２級アルキンアルコールの製造法
JPH07233109A (ja) * 1994-02-24 1995-09-05 Sumitomo Chem Co Ltd 光学活性なアルコール誘導体およびその製造法
JPH09107989A (ja) * 1995-10-19 1997-04-28 Daiso Co Ltd 光学活性化合物の製造法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002057411A2 (fr) * 2000-12-01 2002-07-25 Diversa Corporation Enzymes hydrolase et utilisation de ceux-ci dans la resolution cinetique
WO2002057411A3 (fr) * 2000-12-01 2004-02-12 Diversa Corp Enzymes hydrolase et utilisation de ceux-ci dans la resolution cinetique

Also Published As

Publication number Publication date
JP3550688B2 (ja) 2004-08-04

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