Synthesis of the marine sponge cycloheptapeptide stylopeptide 1

George Pettit, Stuart R. Taylor

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The solution-phase synthesis of the marine sponge stylopeptide 1 (2), cyclo-(Leu-Ile-Phe-Ser-Pro-Ile-Pro), was conveniently accomplished using N-terminal Fmoc- and C-terminal tert-butyl ester protection with tert-butyl ether side-chain blocking for serine. Peptide bond formation for each step except for the final cyclization was effected with diethyl phosphorocyanidate to give the linear heptapeptide in 19% yield. Both TBTU (4) or BOP-Cl (5) were used to cyclize the heptapeptide and resulted in 67% and 13% yields of stylopeptide 1 (2), respectively. Peptide 2 was obtained in 11% overall yield based on the TBTU cyclization procedure. The general approach represents a useful improvement in the synthesis of such cyclic peptides. The synthetic stylopeptide 1 (2) proved to be identical with the natural product.

Original languageEnglish (US)
Pages (from-to)2322-2325
Number of pages4
JournalJournal of Organic Chemistry
Volume61
Issue number7
DOIs
StatePublished - Apr 5 1996

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Cyclization
Cyclic Peptides
Peptides
Biological Products
Ether
Serine
Esters
bis(2-oxo-3-oxazolidinyl)phosphinic chloride
cyclo(isoleucyl-leucyl)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of the marine sponge cycloheptapeptide stylopeptide 1. / Pettit, George; Taylor, Stuart R.

In: Journal of Organic Chemistry, Vol. 61, No. 7, 05.04.1996, p. 2322-2325.

Research output: Contribution to journalArticle

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