Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds in organic solvent

Regioselective Michael addition of purine derivatives to alpha,beta-unsaturated carbonyl compounds could be catalyzed by D-aminoacylase amano (DA) in DMSO. The influence of reaction conditions on the Michael addition, including solvent, temperature, and enzyme concentration was systematically investigated. Then we extended this methodology to Six Structurally diverse purine derivatives and a variety of alpha,beta-unsaturated carbonyl compounds. 21 Michael adducts were selectively synthesized in moderate to high yields. It is the first report on enzyme-catalyzed Michael addition for the preparation of purine derivatives. (C) 2009 Elsevier Ltd. All rights reserved.