Chemical modification of lipases with various hydrophobic groups improves their enantioselectivity in hydrolytic reactions

Shin ichi Ueji, Ai Ueda, Hiroyuki Tanaka, Keiichi Watanabe, Takashi Okamoto, Yasuhito Ebara

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Semi-purified lipases from Candida rugosa, Pseudomonas cepacia and Alcaligenes sp. were chemically modified with a wide range of hydrophobic groups such as benzyloxycarbonyl, p-nitrobenzyloxycarbonyl, pmethoxybenzyloxycarbonyl, t-butoxycarbonyl, lauroyl and acetyl moieties. The Candida rugosa lipase MY modified with the benzyloxycarbonyl group (modification ratio = 84%) brought about a 15-fold increase in enantioselectivity (E value) towards the hydrolysis of racemic butyl 2-(4-ethylphenoxy)propionate in an aqueous buffer solution, although the enzymatic activity was decreased. The origin of the enantioselectivity enhancement by chemical modification of the lipase is attributed to a significant deceleration in the initial reaction rate for the incorrectly binding enantiomer.

Original languageEnglish
Pages (from-to)83-87
Number of pages5
JournalBiotechnology Letters
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 1 2003
Externally publishedYes

Keywords

  • Chemical modification
  • Enantioselectivity
  • Far-ultraviolet circular dichroism
  • Hydrolysis
  • Lipase

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

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