Natural dolapyrrolidone: Isolation and absolute stereochemistry of a substructure of bioactive peptides

Ayana Murakami, Jun ichi Hayashi, Kazunobu Igawa, Miki Tsutsumi, Katsuhiko Tomooka, Hiroshi Nagai, Tatsuo Nehira

研究成果: Contribution to journalArticle査読

抄録

During the course of our chemical analysis of the hydrophilic fractions from marine cyanobacterium Moorena producens, we have isolated natural dolapyrrolidone (Dpy, 1), a natural pyrrolidone derived from phenylalanine, for the first time as a single compound. Compound 1, with an (S)-l absolute stereochemistry, was previously identified as a substructure that is common among several bioactive natural peptides. Surprisingly, the absolute stereochemistry of the isolated natural 1, determined through total synthesis, was (R)-d. This result was unambiguously determined by HPLC analysis using a chiral stationary column by comparing the retention times of the natural 1 and authentic samples of synthetic enantiomers. To verify the unexpected result, the absolute stereochemistry of the natural 1 was confirmed by X-ray crystallographic analysis of Pt-complex derivative using the synthetic enantiomer.

本文言語英語
ページ(範囲)1152-1159
ページ数8
ジャーナルChirality
32
9
DOI
出版ステータス出版済み - 9 1 2020

All Science Journal Classification (ASJC) codes

  • 分析化学
  • 触媒
  • 薬理学
  • 創薬
  • 分光学
  • 有機化学

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