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Practical and Convenient Enzymatic Synthesis of Enantiopure α-Amino Acids and Amides

2002; American Chemical Society; Volume: 67; Issue: 18 Linguagem: Inglês

10.1021/jo0256282

1520-6904

Mei‐Xiang Wang, Shuang‐Jun Lin,

Chemical Synthesis and Analysis

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted dl-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford d-(−)-α-amino acid amides 2 and l-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high l-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of d-(−)-α-phenylglycine amide, biotransformation of dl-phenylglycine nitrile was applied in practical scale to produce both d- and l-phenylglycines in high optical purity.