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Convergent synthesis and biological evaluation of syringolin a and derivatives as eukaryotic 20s proteasome inhibitors


Clerc, J; Schellenberg, B; Groll, M; Bachmann, A S; Huber, R; Dudler, R; Kaiser, M (2010). Convergent synthesis and biological evaluation of syringolin a and derivatives as eukaryotic 20s proteasome inhibitors. European Journal of Organic Chemistry, 2010(21):3991-4003.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Plant and Microbial Biology
Dewey Decimal Classification:580 Plants (Botany)
Language:English
Date:2010
Deposited On:24 Jan 2011 15:46
Last Modified:17 Feb 2018 17:39
Publisher:Wiley-Blackwell
ISSN:1099-0690
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/ejoc.201000317

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