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Solid-phase synthesis of C-terminally modified peptides

✍ Scribed by Hefziba T. Ten Brink; Joris T. Meijer; Remon V. Geel; Mark Damen; Dennis W. P. M. Löwik; Jan C. M. van Hest

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
128 KB
Volume
12
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.

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