A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents

Chun Sheng Chang; Shau Wei Tsai

doi:10.1016/S0141-0229(96)00222-0

A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents

Chun Sheng Chang, Shau Wei Tsai^*

^*Corresponding author for this work

National Cheng Kung University

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

47 Scopus citations

Abstract

A facile enzymatic synthesis process has been developed to directly prepare the 4-morpholinoethyl ester prodrug of (s)-Naproxen from racemic Naproxen using lipases as the biocatalysts in the organic solvent. With the careful selection of lipase (Lipase MY) and reaction medium (cyclohexane), a high enantiomeric ratio of 136 for the enzyme was obtained. A Ping-Pong Bi Bi mechanism with competitive inhibition by the alcohol was illustrated from the variation of initial rates with substrate concentrations.

Original language	English
Pages (from-to)	635-639
Number of pages	5
Journal	Enzyme and Microbial Technology
Volume	20
Issue number	8
DOIs	https://doi.org/10.1016/S0141-0229(96)00222-0
State	Published - 06 1997
Externally published	Yes

Keywords

(s)-naproxen ester
Esterification
Lipase
Prodrug

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10.1016/S0141-0229(96)00222-0

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title = "A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents",

abstract = "A facile enzymatic synthesis process has been developed to directly prepare the 4-morpholinoethyl ester prodrug of (s)-Naproxen from racemic Naproxen using lipases as the biocatalysts in the organic solvent. With the careful selection of lipase (Lipase MY) and reaction medium (cyclohexane), a high enantiomeric ratio of 136 for the enzyme was obtained. A Ping-Pong Bi Bi mechanism with competitive inhibition by the alcohol was illustrated from the variation of initial rates with substrate concentrations.",

keywords = "(s)-naproxen ester, Esterification, Lipase, Prodrug",

author = "Chang, \{Chun Sheng\} and Tsai, \{Shau Wei\}",

year = "1997",

month = jun,

doi = "10.1016/S0141-0229(96)00222-0",

language = "英语",

volume = "20",

pages = "635--639",

journal = "Enzyme and Microbial Technology",

issn = "0141-0229",

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number = "8",

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TY - JOUR

T1 - A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents

AU - Chang, Chun Sheng

AU - Tsai, Shau Wei

PY - 1997/6

Y1 - 1997/6

N2 - A facile enzymatic synthesis process has been developed to directly prepare the 4-morpholinoethyl ester prodrug of (s)-Naproxen from racemic Naproxen using lipases as the biocatalysts in the organic solvent. With the careful selection of lipase (Lipase MY) and reaction medium (cyclohexane), a high enantiomeric ratio of 136 for the enzyme was obtained. A Ping-Pong Bi Bi mechanism with competitive inhibition by the alcohol was illustrated from the variation of initial rates with substrate concentrations.

AB - A facile enzymatic synthesis process has been developed to directly prepare the 4-morpholinoethyl ester prodrug of (s)-Naproxen from racemic Naproxen using lipases as the biocatalysts in the organic solvent. With the careful selection of lipase (Lipase MY) and reaction medium (cyclohexane), a high enantiomeric ratio of 136 for the enzyme was obtained. A Ping-Pong Bi Bi mechanism with competitive inhibition by the alcohol was illustrated from the variation of initial rates with substrate concentrations.

KW - (s)-naproxen ester

KW - Esterification

KW - Lipase

KW - Prodrug

UR - https://www.scopus.com/pages/publications/0031172576

U2 - 10.1016/S0141-0229(96)00222-0

DO - 10.1016/S0141-0229(96)00222-0

M3 - 文章

AN - SCOPUS:0031172576

SN - 0141-0229

VL - 20

SP - 635

EP - 639

JO - Enzyme and Microbial Technology

JF - Enzyme and Microbial Technology

IS - 8

ER -

A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents

Abstract

Keywords

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