Convergent synthesis and biological evaluation of syringolin A and derivatives as eukaryotic 20S proteasome inhibitors

Clerc, Jérôme, Schellenberg, Barbara, Groll, Michael, Bachmann, André S., Huber, Robert, Dudler, Robert and Kaiser, Markus 2010. Convergent synthesis and biological evaluation of syringolin A and derivatives as eukaryotic 20S proteasome inhibitors. European Journal of Organic Chemistry 2010 (21) , pp. 3991-4003. 10.1002/ejoc.201000317

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Abstract

A convergent synthesis of SylA was developed and consists of the synthesis of a fully functionalized macrocycle, which is subsequently coupled with a urea moiety. For cyclization, ring-closing metathesis of a conformationally preorganized precursor was employed. The established synthetic route was then applied to the synthesis of SylA derivatives by using various peptidic side chains for decoration of the SylA macrocycle. The resulting collection of SylA analogues was tested for proteasome inhibition, revealing PEGylated SylA derivatives as the most potent proteasome inhibitors

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Biosciences
Subjects:	Q Science > Q Science (General)
Uncontrolled Keywords:	synthetic methods; natural products; biological activity; metathesis; inhibitors
Publisher:	John Wiley & Sons
ISSN:	1434-193X
Last Modified:	24 Jun 2017 08:42
URI:	https://orca.cardiff.ac.uk/id/eprint/18139

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