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

George Pettit, Cedric W. Holzapfel

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

By employing a series of peptide bond forming reactions followed by a 2,4,5-trichlorophenol active ester promoted cyclization the synthesis of cyclo-[L-Val-L-Leu-L-Pro-(R and S)-(gln)Thz-(gly)Thz] (2) was accomplished. Neither of the diastereomers was identical with the Indian Ocean sea hare cell growth inhibitory constituent dolastatin 3. However, the mass spectra of the synthetic cyclic pentapeptides (2) closely approximated that of the natural product, suggesting a close structural relationship. The El mass spectral fragmentation of cyclic peptides 2 and of two other structurally related cyclic pentapeptides was discussed.

Original languageEnglish (US)
Pages (from-to)4586-4590
Number of pages5
JournalJournal of Organic Chemistry
Volume51
Issue number24
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Organic Chemistry

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