Microbial deracemization of α-substituted carboxylic acids

Control of the reaction path

Dai Ichiro Kato, Kenji Miyamoto, Hiromichi Ohta

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A novel approach to preparing optically active α-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-phenylpropanoic acid, which indicates that the deracemization is a competitive reaction against the α-oxidation pathway of fatty acid metabolism.

Original languageEnglish
Pages (from-to)2965-2973
Number of pages9
JournalTetrahedron Asymmetry
Volume15
Issue number18
DOIs
Publication statusPublished - 2004 Sep 20

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Carboxylic Acids
Carboxylic acids
carboxylic acids
Nocardia
Oxidation
Acids
Fatty Acids
Fatty acids
Metabolism
oxidation
acids
metabolism
Substrates
fatty acids
3-phenylpropionic acid
cells

ASJC Scopus subject areas

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

Cite this

Microbial deracemization of α-substituted carboxylic acids : Control of the reaction path. / Kato, Dai Ichiro; Miyamoto, Kenji; Ohta, Hiromichi.

In: Tetrahedron Asymmetry, Vol. 15, No. 18, 20.09.2004, p. 2965-2973.

Research output: Contribution to journalArticle

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