Conformational analysis of natural products using long-range carbon-proton coupling constants: Three-dimensional structure of okadaic acid in solution

Nobuaki Matsumori, Michio Murata, Kazuo Tachibana

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54 Citations (Scopus)

Abstract

Long-range carbon-proton coupling constants (2,3JC,H) are known to depend on the dihedral angles as is the well-known case with interproton couplings. The precise measurement of these J values were carried out using hetero half-filtered TOCSY and phase-sensitive HMBC on a marine natural product, okadaic acid. From the obtained values together with 3JH,H we disclosed the conformations of okadaic acid in organic and aqueous solutions (CD3OD-CDCl3 or NaOD/D2O), which resembled each other and that obtained for its crystalline o-bromobenzyl ester. The successful result in the present conformational study, even though as an exmaple, demonstrated this methodology to be powerful in elucidation of conformations and configurations of acyclic or macrocyclic portions in natural products of this size.

Original languageEnglish
Pages (from-to)12229-12238
Number of pages10
JournalTetrahedron
Volume51
Issue number45
DOIs
Publication statusPublished - Nov 6 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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