Introduction of Functional Groups into Peptides via N-Alkylation

Organic Letters, 2008, 10, 2015-18 published on 12.04.2008
organic letters; online article
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.

TU München
Helmholtz München
MPI of Neurobiology
MPI of Biochemistry