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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1152-1159
Number of pages8
JournalChirality
Volume32
Issue number9
DOIs
Publication statusPublished - Sep 1 2020

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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