Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone

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  • Fuse Shinichiro
    Institute of Innovative Research, Tokyo Institute of Technology
  • Tanaka Hiroshi
    School of Materials and Chemical Technology, Tokyo Institute of Technology
  • Takahashi Takashi
    Department of Pharmaceutical Sciences, Yokohama University of Pharmacy
  • Doi Takayuki
    Graduate School of Pharmaceutical Sciences, Tohoku University

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  • マンノペプチマイシンアグリコンの合成と立体配置訂正
  • マンノペプチマイシンアグリコン ノ ゴウセイ ト リッタイ ハイチ テイセイ

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Abstract

<p>Mannopeptimycin is an attractive drug candidate due to its strong antimicrobial activity against drug-resistant strains. However, detailed elucidation of structure-activity relationship and its mode of action has been hampered because the chemical synthesis of the densely functionalized aglycone moiety consisting of cyclic hexapeptide was not established. The key point in the synthesis of the aglycone was the construction of densely functionalized unnatural amino acids, Aiha-A and Aiha-B. This account describes isolation, structural determination of mannopeptimycins, previously reported synthesis of Aiha-A and Aiha-B as well as our short-step, high-yielding synthesis of Aihas leading to the first synthesis of mannopeptimycin aglycone with stereochemistry revision of originally proposed structure.</p>

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