文献类型：期刊文献

中文题名：外消旋薄荷醇对映选择性酶促酯化中酸酐与羧酸的比较研究

英文题名：Comparison of Acid Anhydrides with Carboxylic Acids in Enantioselective Enzymatic Esterification of Racemic Methol

作者：许建和[1,2];朱洁[1,2];川本卓男[1,2];田中渥夫[1,2];胡英[1,2]

机构：[1]华东理工大学生物反应器国家重点实验室;[2]京都大学工学部合成/生物化学科应用生化研究室

年份：1997

卷号：13

期号：4

起止页码：387

中文期刊名：生物工程学报

外文期刊名：Chinese Journal of Biotechnology

收录：CSTPCD;;Scopus;北大核心:【北大核心1996】；CSCD:【CSCD2011_2012】；PubMed;

基金：国家自然科学基金

语种：中文

中文关键词：薄荷醇;酶促酯化;羧酸;酸酐;酶工程

外文关键词：Menthol,enzymatic esterification,carboxylic acid,acid anhydride

摘要：利用脂肪酶在有机溶剂中催化对映选择性酯化反应对外消旋薄荷醇进行了有效的光学拆分。对分别使用酸酐和相应的游离羧酸作酰基给体时的反应性能进行了比较。发现酸酐的反应性远高于对应的游离羧酸，但在酶的催化作用下酸酐易水解成为游离羧酸；在微水系统中使用过高浓度的酸酐会导致酶缺水而失活，同时会促进手性醇的非选择性酯化，从而降低产物的光学纯度。然而，在连续流加丙酸酐的半批式反应系统中，所有这些缺点均可有效地克服。与使用游离丙酸的批式反应系统相比，ｄｌ薄荷醇的反应时间缩短了一半，酶的稳定性大幅度提高，而产物ｌ薄荷醇酯的光学纯度不相上下（＞９８％ｅ）。
Optical resolution of racemic menthol has been efficiently achieved by lipase catalyzed enantioselective esterification in an organic solvent.The performance of the reaction using an acid anhydride as an acyl donor was compared with that using its corresponding free acid.The reactivities of acid anhydrides were found to be higher than their corresponding free acids,but acid anhydrides were also found easy to be hydrolyzed into free acids under the catalysis of the same enzyme.The existence of too high concentration of an acid anhydride in a micro aqueous reaction system will cause dehydration and thus deactivation of the enzyme,and will enhance non selective esterification of a chiral alcohol,which will reduce the optical purity of the product.All these drawbacks,however,could be effectively overcome in a semi batch reaction system into which propionic anhydride was continuously fed.This system showed some advantages over a batch reaction system using free propionic acid:the reaction time of dl menthol was shortened by half,the stability of the enzyme was much enhanced,and the optical purity of the product ( l menthyl ester) was kept at a similarly high leve(>98%ee).