Enantioselective acylation of chiral amines catalysed by aminoacylase I

Aminoacylase (E.C. 3.5.1.14) from Aspergillus melleus mediated the acylation of the primary amino group in a range of primary arylalkylamines and amino alcohols in anhydrous organic medium. The commonly used vinyl and isopropenyl esters proved to be unsuitable acyl donors because rapid uncatalysed aminolysis occurred in the presence of these additives. The unwanted aminolysis reaction could be suppressed by performing the enzymatic reaction in tert-butyl methyl ether medium with methyl 2-methoxyacetate as the acyl donor. We found that chiral amines were acylated with poor to moderate enantioselectivity. in contrast with the quantitative enantiodiscrimination that is commonly observed with the corresponding alcohols. (C) 2002 Published by Elsevier Science Ltd.