Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents

Shau Wei Tsai; Bih Yuan Liu; Chun Sheng Chang

doi:10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F

Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents

Shau Wei Tsai^*, Bih Yuan Liu, Chun Sheng Chang

^*Corresponding author for this work

National Cheng Kung University

Research output: Contribution to journal › Journal Article › peer-review

29 Scopus citations

Abstract

The kinetics of enantioselective esterification of racemic Naproxen with trimethylsilyl methanol by Candida cylindracea lipase (triacylglycerol ester hydrolases, EC 3.1.1.3) were examined in various organic mixtures. The effects of solvent hydrophobicity on the activity, selectivity and stability of the enzyme and Naproxen solubility were investigated. Parabolic correlation for the dependence of the kinetic constants and Naproxen solubility on solvent hydrophobicity was found. A mixture of 60% isooctane and 40% toluene (v/v) was selected as the best reaction medium in which improvement of (S)-Naproxen ester productivity was obtained.

Original language	English
Pages (from-to)	156-162
Number of pages	7
Journal	Journal of Chemical Technology and Biotechnology
Volume	65
Issue number	2
DOIs	https://doi.org/10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F
State	Published - 02 1996
Externally published	Yes

Keywords

Esterification
Lipase
Naproxen
Organic mixture

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F

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title = "Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents",

abstract = "The kinetics of enantioselective esterification of racemic Naproxen with trimethylsilyl methanol by Candida cylindracea lipase (triacylglycerol ester hydrolases, EC 3.1.1.3) were examined in various organic mixtures. The effects of solvent hydrophobicity on the activity, selectivity and stability of the enzyme and Naproxen solubility were investigated. Parabolic correlation for the dependence of the kinetic constants and Naproxen solubility on solvent hydrophobicity was found. A mixture of 60% isooctane and 40% toluene (v/v) was selected as the best reaction medium in which improvement of (S)-Naproxen ester productivity was obtained.",

keywords = "Esterification, Lipase, Naproxen, Organic mixture",

author = "Tsai, {Shau Wei} and Liu, {Bih Yuan} and Chang, {Chun Sheng}",

year = "1996",

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T1 - Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents

AU - Tsai, Shau Wei

AU - Liu, Bih Yuan

AU - Chang, Chun Sheng

PY - 1996/2

Y1 - 1996/2

N2 - The kinetics of enantioselective esterification of racemic Naproxen with trimethylsilyl methanol by Candida cylindracea lipase (triacylglycerol ester hydrolases, EC 3.1.1.3) were examined in various organic mixtures. The effects of solvent hydrophobicity on the activity, selectivity and stability of the enzyme and Naproxen solubility were investigated. Parabolic correlation for the dependence of the kinetic constants and Naproxen solubility on solvent hydrophobicity was found. A mixture of 60% isooctane and 40% toluene (v/v) was selected as the best reaction medium in which improvement of (S)-Naproxen ester productivity was obtained.

AB - The kinetics of enantioselective esterification of racemic Naproxen with trimethylsilyl methanol by Candida cylindracea lipase (triacylglycerol ester hydrolases, EC 3.1.1.3) were examined in various organic mixtures. The effects of solvent hydrophobicity on the activity, selectivity and stability of the enzyme and Naproxen solubility were investigated. Parabolic correlation for the dependence of the kinetic constants and Naproxen solubility on solvent hydrophobicity was found. A mixture of 60% isooctane and 40% toluene (v/v) was selected as the best reaction medium in which improvement of (S)-Naproxen ester productivity was obtained.

KW - Esterification

KW - Lipase

KW - Naproxen

KW - Organic mixture

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U2 - 10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F

DO - 10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F

M3 - 文章

AN - SCOPUS:0029671389

SN - 0268-2575

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JO - Journal of Chemical Technology and Biotechnology

JF - Journal of Chemical Technology and Biotechnology

IS - 2

ER -

Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents

Abstract

Keywords

UN SDGs

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