Rational Design of an l-Histidine-Derived Minimal Artificial Acylase for the Kinetic Resolution of Racemic Alcohols

This communication describes the rational design of an l-histidine-derived minimal artificial acylase. Our new artificial acylase, tert-butyldiphenylsilyl ether of N-(2,4,6-triisopropylbenzenesulfonyl)-π(Me)-l-histidinol, is a simple and small molecule (molecular weight = 660) that contains only one chiral carbon center that originates from natural l-histidine. The kinetic acylation of racemic secondary alcohols induced by this compound showed an S (k_fast/k_slow) value of up to 93. A reusable polystyrene-bound artificial acylase was also developed to examine its practical usability.