一种解决皱褶假丝酵母脂肪酶在三苯甲酰化葡萄糖苷酰化反应中区域选择性的方法。

An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides.

作者信息

Palocci C, Falconi M, Alcaro S, Tafi A, Puglisi R, Ortuso F, Botta M, Alberghina L, Cernia E

机构信息

Dipartimento di Chimica, Università degli Studi di Roma "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy.

出版信息

J Biotechnol. 2007 Mar 10;128(4):908-18. doi: 10.1016/j.jbiotec.2006.08.019. Epub 2007 Jan 13.

DOI:10.1016/j.jbiotec.2006.08.019

PMID:17321623

Abstract

Candida rugosa lipase crude preparations (CRL) catalyse the regioselective acylation of methyl 6-O-trytil beta-d-glucopyranoside in organic solvents, using vinyl acetate as acyl donor. The ratio of the two products formed, namely methyl 2-O acetyl 6-O-trytil beta-d-glucopyranoside and methyl 3-O acetyl 6-O-trytil beta-d-glucopyranoside was found to be markedly affected by the nature of the reaction medium. In hydrophobic solvents values up to 80% of the monoacetylated product in position C-3 were obtained compared to less than 30% in solvents with low hydrophobicity. Computational studies were carried out to simulate the interactions between methyl 6-O-trytil beta-d-glucopyranoside and both CRL and the solvents, in order to rationalize the experimental results.

摘要

皱褶假丝酵母脂肪酶粗制品（CRL）在有机溶剂中，以醋酸乙烯酯作为酰基供体，催化6-O-三苯甲基-β-D-吡喃葡萄糖苷甲酯的区域选择性酰化反应。所形成的两种产物，即2-O-乙酰基-6-O-三苯甲基-β-D-吡喃葡萄糖苷甲酯和3-O-乙酰基-6-O-三苯甲基-β-D-吡喃葡萄糖苷甲酯的比例，被发现受到反应介质性质的显著影响。在疏水性溶剂中，C-3位单乙酰化产物的比例高达80%，而在低疏水性溶剂中则不到30%。进行了计算研究，以模拟6-O-三苯甲基-β-D-吡喃葡萄糖苷甲酯与CRL及溶剂之间的相互作用，从而合理解释实验结果。