Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

Masaki Kita, Masami Watanabe, Noboru Takada, Kiyotake Suenaga, Kaoru Yamada, Daisuke Uemura

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

Original languageEnglish
Pages (from-to)6405-6412
Number of pages8
JournalTetrahedron
Volume58
Issue number32
DOIs
Publication statusPublished - 2002 Aug 5
Externally publishedYes

Keywords

  • Isolation
  • Model reaction
  • Natural thiosulfonic acid
  • Structure determination

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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