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Updated: Jul 6, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Introduction of functional groups into peptides via N-alkylation
O Demmer1, I Dijkgraaf, M Schottelius
1Department Chemie, Lehrstuhl II für organische Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Abstract:
An optimized protocol for the mild and selective Fukuyama-Mitsunobu reaction was used for mono- and di- N-alkylation on solid support. Thereby, nonfunctionalized aliphatic and aromatic residues are quickly introduced into transiently protected, primary amines of a linear peptide. N-Alkylation can also be used to implement alkyl chains carrying (protected) functionalities suited for subsequent modification. Applicability of this method is demonstrated by various N-alkylated analogues of a cyclic CXCR4 receptor antagonist originally developed by Fujii et. al.
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