108647-55-8Relevant articles and documents
Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides
Wang, Mei-Xiang,Lin, Shuang-Jun
, p. 6542 - 6545 (2007/10/03)
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.
Nonproteinogenic Amino Acids, IV. - EPC Synthesis of L-(+)-Forphenicine
Weinges, Klaus,Reinel, Ute,Maurer, Wolfgang,Gaessler, Norbert
, p. 833 - 838 (2007/10/02)
Enantiomerically pure L-(+)-forphenicine (12) is synthesized starting from purchasable 3-methoxybenzaldehyde (1) by the use of (4S,5S)-(+)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane (2) as a chiral auxiliary and prussic acid. 12 is identical with the natural product which has been isolated from the culture broth of an Actinomyces species and which is known to be a potent inhibitor of alkaline phosphatase.