Acyclic phenylalkanediols as substrates for the study of enzyme recognition. Regioselective acylation by porcine pancreatic lipase: A structural hypothesis for the enzymatic selectivity

The regioselective acylation of phenylalkanediols catalysed by porcine panc reatic lipase (PPL) was the reaction used-for modelling different areas in the active site of the enzyme. With this aim, different racemic or prochira l (1,n)-diols, with n ranging from 2 to 6 were resolved via transesterifica tion with vinyl acetate, and the results were explained according to microc rystalline enzyme structure. Thus,we describe a logical model for explainin g the enzyme regio and stereoselectivity, based on three residues of the ac tive site (Ser153, Phe216 and His264) which turned out to be crucial for th e substrate binding and transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.