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

…, N Farid, J Li, Z Zhu, J McQuaid, LW Nicholson…

Index: Chaplin, Jennifer A.; Levin, Michael D.; Morgan, Brian; Farid, Nancy; Li, Jen; Zhu, Zuolin; McQuaid, Jeff; Nicholson, Lawrence W.; Rand, Cynthia A.; Burk, Mark J. Tetrahedron Asymmetry, 2004 , vol. 15, # 18 p. 2793 - 2796

Full Text: HTML

Citation Number: 25

Abstract

Enzymatic approaches for the production of amino acids by nitrilases are 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 pH8, allowing preferential enzymatic ...