Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

Nobutoshi Murakami, Satoru Tamura, Weiqi Wang, Tatsuya Takagi, Motomasa Kobayashi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.

Original languageEnglish
Pages (from-to)4323-4336
Number of pages14
JournalTetrahedron
Volume57
Issue number20
DOIs
Publication statusPublished - 2001 May 14

Keywords

  • Arenastatin A
  • Depsipeptide
  • Marine metabolite
  • Restrained molecular dynamics

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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