Dynamic Kinetic Resolution of N-Benzoyl-DL-Amino Acids via Peptide Bond Forming Reactions

Toshifumi      Miyazawa; Takashi      Hamada

Abstract

Dynamic kinetic resolution (DKR) was demonstrated in the carbodiimide-mediated couplings of N-benzoyl-DLamino acids with L-amino acid esters: the yields of the D-L-peptides significantly exceeded 50% in some cases. NBenzoyl- DL-t-leucine afforded the D-L-peptide almost exclusively (up to 96% yield) in the reaction with methyl Lprolinate, which is the most efficient DKR obtained in the field of amino acids and derivatives.

Keywords: Dynamic kinetic resolution (DKR), carbodiimide-mediated couplings, N-benzoyl-DL-amino acids, 5(4H)-oxazolones

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Protein & Peptide Letters

Title: Dynamic Kinetic Resolution of N-Benzoyl-DL-Amino Acids via Peptide Bond Forming Reactions

Volume: 17 Issue: 4

Author(s): Toshifumi Miyazawa and Takashi Hamada

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Keywords: Dynamic kinetic resolution (DKR), carbodiimide-mediated couplings, N-benzoyl-DL-amino acids, 5(4H)-oxazolones

Abstract: Dynamic kinetic resolution (DKR) was demonstrated in the carbodiimide-mediated couplings of N-benzoyl-DLamino acids with L-amino acid esters: the yields of the D-L-peptides significantly exceeded 50% in some cases. NBenzoyl- DL-t-leucine afforded the D-L-peptide almost exclusively (up to 96% yield) in the reaction with methyl Lprolinate, which is the most efficient DKR obtained in the field of amino acids and derivatives.

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Miyazawa Toshifumi and Hamada Takashi, Dynamic Kinetic Resolution of N-Benzoyl-DL-Amino Acids via Peptide Bond Forming Reactions, Protein & Peptide Letters 2010; 17 (4) . https://dx.doi.org/10.2174/092986610790963582