Asymmetric Synthesis of Unnatural Amino Acid-containing Peptides <i>via</i> Direct Asymmetric Reaction of Peptidyl Compounds

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  • Inokuma Tsubasa
    Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University

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Other Title
  • ペプチドへの直接的不斉反応を基盤とした非天然アミノ酸含有ペプチドの新規効率的不斉合成法開発
  • Review for award ペプチドへの直接的不斉反応を基盤とした非天然アミノ酸含有ペプチドの新規効率的不斉合成法開発
  • Review for award ペプチド エ ノ チョクセツテキ フセイ ハンノウ オ キバン ト シタ ヒテンネン アミノサン ガンユウ ペプチド ノ シンキ コウリツテキ フセイ ゴウセイホウ カイハツ

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Abstract

<p>Unnatural amino acids and the peptides bearing such units have gathered much attention due to their interesting biological activities and synthetic utility as chiral building blocks for the synthesis of complex molecules. This paper descibes an asymmetric synthesis of unnatural amino acid derivatives and their subsequent application to the preparation of unnatural amino acid-containing peptides. The α-imino carboxylic acid derivatives, which are common substrates for the synthesis of unnatural amino acids, could be readily prepared by MnO2-mediated oxidation of N-PMP-protected glycine derivatives. This reaction allowed us to synthesize novel derivatives such as α-imino perfluoroalkylesters, imides or thioesters. These compounds are useful for the synthesis of unnatural amino acid derivatives. MnO2-mediated oxidation was further applied to the synthesis of peptidyl imine. Moreover, a new methodology for the synthesis of unnatural amino acid-containing peptides was developed using the thus obtained imino peptides. This novel approach should be useful for the divergent synthesis of peptides possessing varieties of unnatural amino acid moieties.</p>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 138 (11), 1371-1379, 2018-11-01

    The Pharmaceutical Society of Japan

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