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Synthesis of All-l Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers

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posted on 16.07.2010, 00:00 by Kelly A. Fairweather, Nima Sayyadi, Ian J. Luck, Jack K. Clegg, Katrina A. Jolliffe
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.