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

Ayana MurakamiJun-Ichi HayashiKazunobu IgawaMiki TsutsumiKatsuhiko TomookaHiroshi NagaiTatsuo Nehira
Published in: Chirality (2020)
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.
Keyphrases
  • liquid chromatography
  • mass spectrometry
  • magnetic resonance imaging
  • ms ms
  • computed tomography
  • simultaneous determination
  • solid phase extraction
  • contrast enhanced