Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exp osed to the hydrolase enzyme acetylcholinesterase from Electrophorus electr icus. All eight compounds were hydrolyzed by the enzyme. The overall enanti oselectivities were quite high, and the resulting e.e.s were generally >90% . The absolute configurations of the product monoesters were determined thr ough stereochemical correlation. These data revealed that the preferred sit e for enzymatic hydrolysis in seven of the substrates was the pro-S ester f unction, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Scie nce Ltd. All rights reserved.