Synthesis of All- L cyclic tetrapeptides using pseudoprolines as removable turn inducers

Kelly A. Fairweather, Nima Sayyadi, Ian J. Luck, Jack K. Clegg, Katrina A. Jolliffe

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

(Figure Presented) Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.

Original languageEnglish
Pages (from-to)3136-3139
Number of pages4
JournalOrganic Letters
Volume12
Issue number14
DOIs
Publication statusPublished - 16 Jul 2010
Externally publishedYes

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