PROBING THE SPECIFICITY OF THE S-1', LEAVING GROUP, SITE OF SUBTILISIN BACILLUS-LENTUS USING AN ENZYME-CATALYZED TRANSESTERIFICATION REACTION

Subtilisin Bacillus lentus catalyzes transesterifications between N-ac etyl-L-phenylalanine vinyl ester and a wide range of alcohols. Reactio n yields are high when primary alcohols are used, and quantitative wit h methanol. With chiral alcohols, the reaction is enantioselective, an d the stereoselectivity is reversed on going from open chain secondary alcohols to beta-branched primary alcohols. A model is proposed to ac count for this change in absolute configuration preference. (C) 1998 E lsevier Science Ltd. All rights reserved.