Chemoenzymatic approaches to the dynamic kinetic asymmetric synthesis of aromatic amino acids

Enzymatic approaches for the production of amino acids by nitrilases Lire described. Dynamic kinetic asymmetric synthesis conditions were established for the aromatic aminonitriles, phenylglycinonitrile and 4-fluorophenylglycinonitrile, at high pH to produce the corresponding amino acid products in high enantiomeric excess. N-Acylation of aromatic aminonitriles led to spontaneous racemization at pH 8, allowing preferential enzymatic hydrolysis of the (R)-enantiomer to afford the product N-acyl-amino acids in Lip to 99% enantiomeric excess (ee). (C) 2004 Elsevier Ltd. All rights reserved.