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Publication Detail

Title: Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles.

Authors: Qian, Wen-Jian; Park, Jung-Eun; Grant, Robert; Lai, Christopher C; Kelley, James A; Yaffe, Michael B; Lee, Kyung S; Burke Jr, Terrence R

Published In Biopolymers, (2015 Nov)

Abstract: Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring-forming junctions. Interestingly, these cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts.

PubMed ID: 26152807 Exiting the NIEHS site

MeSH Terms: No MeSH terms associated with this publication

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