34996-83-3Relevant academic research and scientific papers
Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides
Wang, Mei-Xiang,Lin, Shuang-Jun
, p. 6542 - 6545 (2002)
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.
Glycine-selective α-carbon-nitrogen bond cleavage of dipeptides by nickel peroxide
Easton, Christopher J.,Eichinger, Sharon K.,Pitt, Michael J.
, p. 5609 - 5616 (2007/10/03)
Nickel peroxide selectively cleaves the α-carbon-nitrogen bond of glycine residues in dipeptide derivatives to give the corresponding amides. The glycine selectivity is attributable to preferential complexation of the reactant residue to nickel peroxide and subsequent reaction via a stable α-centered glycyl radical. The oxidation process serves as a chemical model for peptidylglycine α-amidating monooxygenase (PAM) and, in addition, may have potential for the synthesis of α,β-didehydro amino acid residues within peptides.
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.
