51268-84-9Relevant academic research and scientific papers
A simple approach to amino acids with a diazo function in the side chain starting from aspartic acid
Burger,Rudolph,Neuhauser,Gold
, p. 1150 - 1156 (2007/10/02)
[2,2-Bis(trifluoromethyl)-5-oxo-1,3-oxazolidin-4-yl]acetic acid chloride (2) and diazoalkanes react to give the amino acid derivatives 2,2-bis(trifluoromethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-ones 3. Compounds 3 are useful intermediates for the s
Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I
Chenault, H. Keith,Dahmer, Juergen,Whitesides, George M.
, p. 6354 - 6364 (2007/10/02)
Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.
