Lipase-Catalyzed Deacylation by Alcoholysis: A Selective, Useful Transesterification Reaction

Alcoholysis is a transesterification reaction, according to which an ester RCOOR' reacts with an alcohol R"OH with formation of another ester RCOOR" and liberation of the alcohol R'OH. The deacylation may be catalyzed by a lipase in organic solvents and constitutes a useful step in the synthesis of complex molecules where different groups are present. The enzymatic deprotection procedure acquires a particular significance, considering the hydrophobic nature of the substrates and their solubility in organic solvents. In these non-conventional media lipases are still considerably active and a great variety of examples of regio- and chemoselectivity of the enzymatic deacylation have been reported. Application of resolution or asymmetrization procedures to the preparation of stereochemically pure products will also be examined and discussed.