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

doi:10.1007/BF00170922

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 journal › Article › peer-review

44 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 language	English
Pages (from-to)	47-51
Number of pages	5
Journal	Applied Microbiology and Biotechnology
Volume	34
Issue number	1
DOIs	https://doi.org/10.1007/BF00170922
Publication status	Published - Oct 1 1990
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biotechnology
Applied Microbiology and Biotechnology

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10.1007/BF00170922

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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.",

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T1 - Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent

T2 - effects of alcohol chain length

AU - Pan, Shi Hao

AU - Kawamoto, Takuo

AU - Fukui, Toshiaki

AU - Sonomoto, Kenji

AU - Tanaka, Atsuo

PY - 1990/10/1

Y1 - 1990/10/1

N2 - 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.

AB - 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.

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Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent: effects of alcohol chain length

Abstract

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