Solid-phase synthesis of chlorofusin analogues

Woon, Esther C. Y., Arcieri, Mariangela, Wilderspin, Andrew F., Malkinson, John P. and Searcey, Mark ORCID: (2007) Solid-phase synthesis of chlorofusin analogues. Journal of Organic Chemistry, 72 (14). pp. 5146-5151. ISSN 0022-3263

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We report an efficient and versatile solid-phase synthesis through which two series of chlorofusin analogues, one bearing varying chromophores and the other with various amino acid substitutions in the cyclic peptide, were synthesized. These peptides were prepared using a strategy involving side-chain immobilization, on-resin cyclization, and postcyclization modification. The success of these syntheses demonstrates the broad utility of the method. Both series of analogues were evaluated for their inhibitory activity against the p53/MDM2 interaction but were shown to be inactive in the concentration range tested. This suggests that the full chromophore structure may be required for activity.

Item Type: Article
Uncontrolled Keywords: peptide,inhibitor,binding,protein,small-molecule antagonists,mdm2,p53 pathway,in-vivo,discovery
Faculty \ School: Faculty of Science > School of Pharmacy
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 11:09
Last Modified: 24 Oct 2022 01:35
DOI: 10.1021/jo070450a

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