Synthesis of the Dolastatin 3 Isomer cyclo-[L-Pro-L-Leu-L-Val-(-R,S)-(gln)Thz-(gly)Thz]

George Pettit, Cedric W. Holzapfel

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

With application of mixed carbonic anhydride and dicyclohexylcarbodiimide-N-hydroxysuccinimide peptide bond forming methods culminating in a 2,4,5-trichlorophenol active ester promoted cyclization reaction, synthesis (cf., Scheme I) of cyclo-[L-Pro-L-Leu-L-Val-(R,S)-(gln)Thz-(gly)Thz] was completed. Comparison of this cyclic peptide with the Indian Ocean sea hare cell growth inhibitory constituent dolastatin 3 clearly showed that the natural peptide possesses a closely related structure. The high resolution (400 MHz) 1H NMR and 13C NMR spectra of the synthetic peptides were evaluated in detail and suggested that dolastatin 3 may contain (R)-(gln)Thz and/or a modified Pro-Leu-Val sequence.

Original languageEnglish (US)
Pages (from-to)4580-4585
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number24
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of the Dolastatin 3 Isomer cyclo-[L-Pro-L-Leu-L-Val-(-R,S)-(gln)Thz-(gly)Thz]'. Together they form a unique fingerprint.

  • Cite this