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Convenient Solid-Phase Synthesis of Ureido-Pyrimidinone Modified Peptides

✍ Scribed by Patricia Y. W. Dankers; P. J. H. M. Adams; Dennis W. P. M. Löwik; Jan C. M. van Hest; E. W. Meijer

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
318 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Peptides have been modified with quadruple hydrogen bonding ureido‐pyrimidinone moieties to be applied in supramolecular architectures for biomedical applications. A convenient solid‐phase synthesis method was developed to functionalize peptide sequences with ureido‐pyrimidinone units. Two different ureido‐pyrimidinone synthons were used: based on a carbonyldiimidazole‐activated amine or on an isocyanate functionality. Oligopeptides were functionalized on the solid support using two coupling strategies: on the N‐terminus or selectively on the ϵ‐position of a C‐terminal lysine. Several peptides were modified to show the generality of the approach, varying from cell adhesion sequences, to collagen binding peptides and cysteine derivatives which can be used for native chemical ligation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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