Total synthesis and stereochemistry revision of mannopeptimycin aglycone

Shinichiro Fuse, Hiroshi Tanaka, Takashi Takahashi, Takayuki Doi

Research output: Contribution to journalArticle

Abstract

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 mannopepti-mycins, 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.

Original languageEnglish
Pages (from-to)1274-1285
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume75
Issue number12
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • Aglycone
  • Antibiotic
  • Asymmetric aldol
  • Cyclic peptide
  • Glycopeptide
  • Guanidine
  • Macrolactamization
  • Mannopeptimycin
  • Structural revision
  • Unnatural amino acid

ASJC Scopus subject areas

  • Organic Chemistry

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