Confirmation of the absolute configuration at C45 of amphidinol 3

Yoshiyuki Manabe, Makoto Ebine, Nobuaki Matsumori, Michio Murata, Tohru Oishi

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring system was found to be antipodal to that of karlotoxin 2, a structurally related compound recently isolated from the dinoflagellate Karlodinium veneficum. By extensive degradation of the natural product and conversion of the resulting alcohol to an MTPA ester, the absolute configuration at C45 of AM3 was confirmed to be R, supporting the originally proposed structure.

Original languageEnglish
Pages (from-to)2003-2006
Number of pages4
JournalJournal of Natural Products
Volume75
Issue number11
DOIs
Publication statusPublished - Dec 3 2012

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Dinoflagellida
Biological Products
Degradation
Esters
Carbon
Alcohols
Nuclear magnetic resonance
Membranes
amphidinol 3
karlotoxin-2

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Confirmation of the absolute configuration at C45 of amphidinol 3. / Manabe, Yoshiyuki; Ebine, Makoto; Matsumori, Nobuaki; Murata, Michio; Oishi, Tohru.

In: Journal of Natural Products, Vol. 75, No. 11, 03.12.2012, p. 2003-2006.

Research output: Contribution to journalArticle

Manabe, Yoshiyuki ; Ebine, Makoto ; Matsumori, Nobuaki ; Murata, Michio ; Oishi, Tohru. / Confirmation of the absolute configuration at C45 of amphidinol 3. In: Journal of Natural Products. 2012 ; Vol. 75, No. 11. pp. 2003-2006.
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