Revised absolute stereochemistry of natural kulokekahilide-2

Yuuki Takada, Masahiro Umehara, Yoichi Nakao, Junji Kimura

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the 1H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.

Original languageEnglish
Pages (from-to)1163-1165
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number7
DOIs
Publication statusPublished - 2008 Feb 11

Keywords

  • Cytotoxicity
  • Kulokekahilide-2
  • Macrolactamization
  • cis-trans Conformations

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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