Acyclic phenylalkanediols as substrates for the study of enzyme recognition: Synthesis of substrates and enzymatic resolution via hydrolysis and transesterification

Different racemic or prochiral phenyl alkane (1,n)-diols were synthesized, and their resolution was carried out by two different strategies: enzymatic transesterification with vinyl acetate, or enzymatic hydrolysis of their c orresponding diacetates, in both cases catalysed by porcine pancreatic lipa se (PPL). The absolute configuration of the optically enriched reaction pro ducts was determined by formation of Mosher's esters or by the use of the B enzene Sector and Benzene Chirality Rules as obtained from the Circular Dic hroism spectra. (C) 1999 Elsevier Science Ltd. All rights reserved.