Enzymatic hydrolysis of 3,7-diacetoxycloheptene derivatives

Abstract

Hydrolysis of 3,7-diacetoxycycloheptene using electric eel acetylcholinesterase gives optically pure (3R,7S)-3-hydroxy-7-acetoxycycloheptene, and hydrolysis using lipase enzyme from Candida cyclindracea gives the same hydroxy acetate, but in only 44% enantiomeric excess, in contrast to the normal behaviour of lipase which gives (S) alcohols for related hydrolyses; 3,7-diacetoxy-4,6-dimethylcycloheptene (10) is not hydrolysed by acetylcholinesterase, but is readily hydrolysed by lipase to give (3S,4R,6S,7R)-3-hydroxy-7-acetoxy-4,6-dimethylcycloheptene.