Dynamic kinetic resolution of N-benzoyl-DL-amino acids via peptide bond forming reactions.
Dynamic kinetic resolution (DKR) was demonstrated in the carbodiimide-mediated couplings of N-benzoyl-DL-amino acids with L-amino acid esters: the yields of the D-L-peptides significantly exceeded 50% in some cases. N-Benzoyl-DL-t-leucine afforded the D-L-peptide almost exclusively (up to 96% yield) in the reaction with methyl L-prolinate, which is the most efficient DKR obtained in the field of amino acids and derivatives.
Miyazawa
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T
Department of Chemistry, Faculty of Science and Engineering, Konan University, Kobe 658-8501, Japan. miyazawa@ konan-u.ac.jp
Hamada
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T
D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism*; D001565:Benzoates / Q000737:chemistry / Q000378:metabolism*; D055598:Chemical Phenomena; D002851:Chromatography, High Pressure Liquid; D004151:Dipeptides / Q000737:chemistry / Q000378:metabolism*; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D001565:Benzoates; D004151:Dipeptides; D004952:Esters; D010080:Oxazoles