Solid-phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-MDM2 interactions

Malkinson, John P., Zloh, Mire, Kadom, Mohanad, Errington, Rachel, Smith, Paul J. and Searcey, Mark ORCID: https://orcid.org/0000-0003-2273-8949 (2003) Solid-phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-MDM2 interactions. Organic Letters, 5 (26). pp. 5051-5054. ISSN 1523-7060

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Abstract

[GRAPHICS] The first solid-phase synthesis of the chlorofusin peptide is described. The synthesis involved side-chain immobilization of N-alpha-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
Uncontrolled Keywords:	binding,support,protein,p53,chemistry,mdm2,cancer,sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User:	Rachel Smith
Date Deposited:	13 Jun 2011 14:02
Last Modified:	24 Sep 2024 10:11
URI:	https://ueaeprints.uea.ac.uk/id/eprint/32131
DOI:	10.1021/ol0360849

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