The studies on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid with various trialkyl orthoesters as alkoxy group donors are presented. The obtained results indicate that enantioselectivity of presented reaction is closely related to the alkoxy group donor structure. Based on critical analysis of the literature data and our own results we found that the previously recognized mechanism of such transformation is highly unlikely. In this paper we proposed a new revised mechanism explaining the role of alkoxy group donors. For trialkyl orthobenzoates excellent enzymatic kinetic resolution of target substrate was achieved. The presented method is an unique example of an enzymatic promiscuous activity toward esterification of carboxylic acids.

提出了用各种三烷基原酸酯作为烷氧基供体的3-苯基-4-戊烯酸的酶促动力学拆分的研究。获得的结果表明，所呈现的反应的对映选择性与烷氧基供体结构密切相关。基于对文献数据的批判性分析和我们自己的结果，我们发现以前公认的这种转化机制极不可能。在本文中，我们提出了一种新的修订机制，解释了烷氧基供体的作用。对于原苯甲酸三烷基酯，可以实现目标底物的优异酶促动力学拆分。提出的方法是对羧酸酯化的酶促混合活性的独特实例。