59759-67-0Relevant 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.
Synthesis of Acylamino Acid Amides and Acylamino Acids via 2,4-Disubstituted 2-Imidazolin-5-ones
Devasia, Ganapathiplackal M.,Shafi, P. Mohamed
, p. 70 - 72 (2007/10/02)
Unsaturated 2,4-disubstituted 2-imidazolin-5-ones (I) have been reduced with a mixture of hydriodic acid and red phosphorus in the presence of acetic anhydride to give the saturated 2,4-disubstituted 2-imidazolin-5-ones (II) which have been hydrolysed to acylamino acid amides (III) and acylamino acids (IV) with sodium hydroxide solution under different conditions.In all six acylamino acid amides (23 - 51percent yields) and four acylamino acids (26 - 65percent yields) have been prepared.One saturated 2-imidazolin-5-one, namely 2-phenyl-4-benzyl-2-imidazolin-5-one has been isolated from the reaction in 40percent yield and identified.