The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

Yuuki Takada, Masahiro Umehara, Ryosuke Katsumata, Yoichi Nakao, Junji Kimura

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-l-Ala, 24-d-MePhe, 37-l-Ile, 43-d-Ala, 15-d-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure-activity relationships of kulokekahilide-2 and its analogs indicate the importance of an l-amino acid at position 21.

Original languageEnglish
Pages (from-to)659-669
Number of pages11
JournalTetrahedron
Volume68
Issue number2
DOIs
Publication statusPublished - 2012 Jan 14

Keywords

  • Cyclic depsipeptide
  • Cytotoxicity
  • Kulokekahilide-2
  • Structure-activity relationships
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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