Application of microbial enantiofacially selective hydrolysis in natural product synthesis

Osamu Katoh, Takeshi Sugai, Hiromichi Ohta

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.

Original languageEnglish
Pages (from-to)1935-1944
Number of pages10
JournalTetrahedron: Asymmetry
Volume5
Issue number10
DOIs
Publication statusPublished - 1994

Fingerprint

Cucumis sativus
Pichia
Enantiomers
Transesterification
Lipases
Bioreactors
Biological Products
Ketones
Lipase
Diptera
Lipopolysaccharides
hydrolysis
Hydrolysis
Acetates
Alcohols
Oxidation
synthesis
products
bioreactors
secretions

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Application of microbial enantiofacially selective hydrolysis in natural product synthesis. / Katoh, Osamu; Sugai, Takeshi; Ohta, Hiromichi.

In: Tetrahedron: Asymmetry, Vol. 5, No. 10, 1994, p. 1935-1944.

Research output: Contribution to journalArticle

@article{e31c7917308349c0a24a6487f291d869,
title = "Application of microbial enantiofacially selective hydrolysis in natural product synthesis",
abstract = "Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70{\%} yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87{\%}e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95{\%} e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.",
author = "Osamu Katoh and Takeshi Sugai and Hiromichi Ohta",
year = "1994",
doi = "10.1016/S0957-4166(00)86269-2",
language = "English",
volume = "5",
pages = "1935--1944",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - Application of microbial enantiofacially selective hydrolysis in natural product synthesis

AU - Katoh, Osamu

AU - Sugai, Takeshi

AU - Ohta, Hiromichi

PY - 1994

Y1 - 1994

N2 - Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.

AB - Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.

UR - http://www.scopus.com/inward/record.url?scp=0027985562&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027985562&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(00)86269-2

DO - 10.1016/S0957-4166(00)86269-2

M3 - Article

AN - SCOPUS:0027985562

VL - 5

SP - 1935

EP - 1944

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 10

ER -