Synthesis of the biologically active natural product cyclodepsipeptides apratoxin A and its analogues

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14 Citations (Scopus)

Abstract

This paper describes the synthetic studies conducted on a marine natural product, cyclodepsipeptide apratoxin A. Total synthesis of the oxazoline analogue of apratoxin A was achieved. The conversion of oxazoline to thioamide, as well as thioamide formation from a serine-derived compound, were both unsuccessful. However, thiazoline formation from a cysteine-derived compound led to the total synthesis of apratoxin A. An in vivo study on synthetic apratoxin A revealed that it has potent antitumor activity, but with significant toxicity. Solid-phase synthesis of apratoxin A was accomplished using a preformed thiazoline derivative as a coupling unit. This method was used to synthesize several azido-containing analogues as precursors of molecular probes, and these analogues exhibited potent biological activity.

Original languageEnglish
Pages (from-to)735-743
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume62
Issue number8
DOIs
Publication statusPublished - 2014 Aug 1

Keywords

  • Cyclodepsipeptide
  • Cytotoxicity
  • Natural product
  • Solid-phase synthesis
  • Thiazoline
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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