Chemical studies on tuberactinomycin. XI. Semisyntheses of tuberactinomycin analogs with various amino acids in branched part.

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概要

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• Thirty two semisynthetic tuberactinomycins were prepared by introduction of various amino acids to amino group of tuberactinamine N, a cyclic peptide moiety of tuberactinomycin N and O, which was isolated from natural tuberactinomycin N by acid treatment with liberation of γ-hydroxy-β-lysine of the branched part. Among introduced amino acids, β-amino acids were synthesized from corresponding α-amino acids by modified Arndt-Eistert reaction. After couplings of N-protected amino acids with tuberactinamine N, deprotections were carried out to give semisynthetic tuberactinomycins. From their minimum inhibitory concentrations against many bacteria, it was suggested that a branched part effects significantly to the strength of antimicrobial activities though most important active site must locate in the cyclic peptide moiety, and basicity and/or hydrophobicity of the branched part seemed to strengthen the antibacterial activity especially.

• 公益社団法人 日本化学会の論文

著者

• Shiba Tetsuo

  Department Of Chemistry Faculty Of Science Osaka University

• Wakamiya Tateaki

  Department Of Chemistry Faculty Of Science Osaka University

• Teshima Tadashi

  Department Of Chemistry Faculty Of Science Osaka University

• Sakakibara Hideo

  The Research Laboratories, Toyo Jozo Co., Ltd.

• Teshima Tadashi

  Department of Chemistry, Faculty of Science, Osaka University Toyonaka

• Fukukawa Kiyoshi

  The Research Laboratories, Toyo Jozo Co., Ltd.

• Shiba Tetsuo

  Department of Chemistry, Faculty of Science, Osaka University Toyonaka

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