Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles
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Author(s)
Qian, Wen-Jian
Park, Jung-Eun
Lai, Christopher C.
Kelley, James A.
Lee, Kyung S.
Burke, Terrence R.
Grant, Robert A
Yaffe, Michael B
Date Issued
November 2015
Journal
Biopolymers
Publisher
Wiley Blackwell
Citation
Qian, Wen-Jian et al. “Neighbor-Directed Histidine N (τ)-Alkylation: A Route to Imidazolium-Containing Phosphopeptide Macrocycles: Neighbor-Directed Histidine N(τ)-Alkylation.” Biopolymers 104.6 (2015): 663–673.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Biological Engineering
Massachusetts Institute of Technology. Department of Biology
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DOI of Published Version
https://doi.org/10.1002/bip.22698
