Solid phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-mdm2 interactions

Malkinson, J.P., Zloh, M., Kadom, M., Errington, R., Smith, P.J. and Searcey, M. (2003) Solid phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-mdm2 interactions. Organic Letters, 5 . pp. 5051-5054. 10.1021/ol0360849.

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DOI: 10.1021/ol0360849

Abstract

The first solid-phase synthesis of the chlorofusin peptide is described. The synthesis involved side-chain immobilization of N-Fmoc-Asp-ODmab. Synthesis of the linear peptide, initially incorporating racemic Ade8 and unsubstituted ornithine in place of the chromophore-bearing residue, was followed by cyclization on resin and peptide release to give a mixture of diastereomers. Resynthesis identified (by HPLC) the second isomer as analogous to the natural product. Initial biological assays, using an immunofluorescence method, suggest that the compounds are not cytotoxic but do not inhibit the p53/mdm2 interaction.

Item Type:Article
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:113
Journal or Publication Title:Organic Letters
Deposited By:Library Staff
Deposited On:04 Sep 2007
Last Modified:19 Sep 2007 11:12

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