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

Author: Ueji S-i.  

Publisher: Springer Publishing Company

ISSN: 0141-5492

Source: Biotechnology Letters, Vol.25, Iss.1, 2003-01, pp. : 83-87

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Abstract

Semi-purified lipases from Candida rugosa</i>, Pseudomonas cepacia</i> and Alcaligenes</i> sp. were chemically modified with a wide range of hydrophobic groups such as benzyloxycarbonyl, p</i>-nitrobenzyloxycarbonyl, p</i>-methoxybenzyloxycarbonyl, t</i>-butoxycarbonyl, lauroyl and acetyl moieties. The Candida rugosa</i> lipase MY modified with the benzyloxycarbonyl group (modification ratio = 84%) brought about a 15-fold increase in enantioselectivity (E</i> 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.