144790-33-0Relevant academic research and scientific papers
UNUSUAL AMINO ACIDS. III. ASYMMETRIC SYNTHESIS OF 3-ARYLALANINES
Taudien, Stefan,Schinkowski, Klaus,Krause, Hans-Walter
, p. 73 - 84 (2007/10/02)
21 (Z)-α-N-benzoylamino-β-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active α-benzoyl-β-arylalanine derivatives with optical yields in the range of 82-95percent ee using the cationi
Enzymatic Asymmetric Synthesis of α-Amino Acids. Enantioselective Cleavage of 4-Substituted Oxazolin-5-ones and Thiazolin-5-ones
Crich, Joyce Z.,Brieva, Rosario,Marquart, Peer,Gu, Rui-Lin,Flemming, Steffen,Sih, Charles J.
, p. 3252 - 3258 (2007/10/02)
A general enzymatic asymmetric synthesis of L-α-amino acids has been developed.This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically active N-benzoyl-L-α-amino acid methyl esters (ee = 66-98 percent), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically pure N-benzoyl-L-α-amino acids.This synergistic coupling of two enzymes allows the ready preparation of L-α-amino acids of high enantiopurity in yields greater than 50 percent, an inherent advantage over conventional resolution procedures.Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-α-amino acids of high optical purity.
