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Biocatalyzed Regio‐ and Chemoselective Ester Cleavage: Synthesis of Bioactive Molecules
Author(s) -
Barbayianni Efrosini,
Kokotos George
Publication year - 2012
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200035
Subject(s) - biocatalysis , chemistry , combinatorial chemistry , molecule , chemoselectivity , chemical synthesis , selectivity , organic chemistry , alcohol , cleavage (geology) , catalysis , reaction mechanism , biochemistry , materials science , fracture (geology) , composite material , in vitro
Biocatalysis is one of the greenest technologies for the synthesis of bioactive molecules, for which the presence of various functional groups requires selective protection or deprotection processes. The effective combination of protecting group techniques often results in additional chemical synthetic steps. At this point, enzymes can prove very valuable, as they help to circumvent several reaction steps, owing to the selectivity they show for a particular group. Specifically, carboxylic acid and alcohol functionalities, as well as esters, are of high importance for the biological properties of certain molecules. Esters are enzyme‐labile moieties, a characteristic that many drugs activity is based on. Ester cleavage is also required for synthesis, where beyond any doubt, the majority of reactions and conditions must be highly selective. This review aims to highlight a number of examples in the literature relative to regio‐ and chemoselective biocatalytic deprotection processes of the carboxyl and hydroxyl moieties, used in the synthesis of pharmaceuticals, bioactive molecules, and drug precursors.