Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent

effects of alcohol chain length

Shi Hao Pan, Takuo Kawamoto, Toshiaki Fukui, Kenji Sonomoto, Atsuo Tanaka

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Optical resolution of racemic carboxylic acids containing a halogen atom was attempted with stereoselective esterificatiob by Celite-adsorbed hydrolases in organic solvents. As lipase OF 360 from Candida cylindracea was found to stereoselectively esterify 2-(4-chlorophenoxy)propanoic acid, the (R)-enantiomer (d-isomer) of which is an important herbicide, the effects of alcohol chain length on stereoselectivity as well as reaction rate were investigated. The results revealed that the alcohol chain length markedly affected the stereoselective esterification of 2-(4-chlorophenoxy)propanoic acid: longer-chain alcohols, such as tetradecanol, served as excellent substrates for optical resolution of the acid, although the reaction rate was moderate.

Original languageEnglish
Pages (from-to)47-51
Number of pages5
JournalApplied Microbiology and Biotechnology
Volume34
Issue number1
DOIs
Publication statusPublished - Oct 1 1990
Externally publishedYes

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Halogens
Esterification
Carboxylic Acids
Lipase
Alcohols
Diatomaceous Earth
Herbicides
Hydrolases
Candida
Acids
2-(4-chlorophenoxy)propionic acid

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent : effects of alcohol chain length. / Pan, Shi Hao; Kawamoto, Takuo; Fukui, Toshiaki; Sonomoto, Kenji; Tanaka, Atsuo.

In: Applied Microbiology and Biotechnology, Vol. 34, No. 1, 01.10.1990, p. 47-51.

Research output: Contribution to journalArticle

Pan, Shi Hao ; Kawamoto, Takuo ; Fukui, Toshiaki ; Sonomoto, Kenji ; Tanaka, Atsuo. / Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent : effects of alcohol chain length. In: Applied Microbiology and Biotechnology. 1990 ; Vol. 34, No. 1. pp. 47-51.
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