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  • Title: Solid-phase synthesis of C-terminally modified peptides.
    Author: Ten Brink HT, Meijer JT, Geel RV, Damen M, Löwik DW, van Hest JC.
    Journal: J Pept Sci; 2006 Nov; 12(11):686-92. PubMed ID: 16953495.
    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.
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