Antineoplastic agents. 400. Synthesis of the Indian ocean marine sponge cyclic heptapeptide phakellistatin 2

George Pettit, Monte R. Rhodes, Rui Tan

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

Solution-phase synthesis of the marine sponge constituent phakellistatin 2 (1), cyclo(Tyr-Pro-Phe-Pro-Ile-Ile-Pro), was completed using a combination of stepwise coupling and (4 + 3) segment condensation. Use of diethyl phosphorocyanidate for the peptide bond formations gave the linear heptapeptide in 54% yield. Cyclization was achieved in high yields utilizing TBTU (2), BOP-C1 (3), PyBroP (4), and HOAt (5), resulting in 50-65% yields of phakellistatin 2 (1) depending on the method employed. The synthetic cyclic peptide was chemically but not biologically identical with the natural product.

Original languageEnglish (US)
Pages (from-to)409-414
Number of pages6
JournalJournal of Natural Products
Volume62
Issue number3
DOIs
StatePublished - Mar 1999

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Antineoplastic agents. 400. Synthesis of the Indian ocean marine sponge cyclic heptapeptide phakellistatin 2'. Together they form a unique fingerprint.

  • Cite this