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Delayed fibril formation of amylin(20-29) by incorporation of alkene dipeptidosulfonamide isosteres obtained by solid phase olefin cross metathesis
Authors
Arwin J. Brouwer
Ronald C. Elgersma
+3 more
Monika Jagodzinska
Rob M.J. Liskamp
Dirk T.S. Rijkers
Publication date
1 January 2008
Publisher
Abstract
The synthesis of a new peptidomimetic structure, the alkene dipeptidosulfonamide isostere, is described. The synthesis is based on a cross metathesis reaction between two allylic building blocks, both in solution and on the solid phase. This method was also applicable to the solid phase synthesis of alkene dipeptide isosteres. Derivatives of amylin(20-29) containing the alkene dipeptidosulfonamide isostere as well as the alkene dipeptide isostere were successfully synthesized using the solid phase cross metathesis method. Investigation of relations between structure and fibril formation of these amylin(20-29) derivatives showed retardation of fibril formation and altered secondary structures, compared to native amylin(20-29). © 2007 Elsevier Ltd. All rights reserved
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Last time updated on 30/11/2019