Chemoselective enzymatic preparation of N-hydroxyalkylacrylamides, monomers for hydrophilic polymer matrices

A lipase-catalyzed procedure is described for the preparation of N-hydroxyalkylacrylamides useful among a number of electrophoretical applications such as capillary and gel electrophoresis. The N-hydroxyalkylacrylamides were prepared through an aminolysis reaction of alkanolamines on ethyl acrylate. The reaction was catalyzed by Candida antarctica lipase. The addition of radical inhibitors improved chemoselectivity and amides were obtained in high yield and purity at room temperature. (c) 2006 Elsevier B.V. All rights reserved.