Transition‐State Model for Subtilisin‐Catalyzed Transesterifications of Secondary Alcohols.

Abstract In the subtilisin-catalyzed transesterifications of a variety of secondary alcohols, the ( S )-enantiomers were acylated faster. Kinetic measurements indicated that the enantioselectivity originates from chiral discrimination in the transition state. A transition-state model capable of explaining the S -preference of subtilisin toward secondary alcohols has been proposed.