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

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. These cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Furthermore, neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts.

Authors:
 [1];  [2];  [3];  [1];  [1];  [3];  [2];  [1]
  1. National Cancer Inst., Frederick, MD (United States)
  2. National Cancer Inst., Bethesda, MD (United States)
  3. Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
USDOE
OSTI Identifier:
1228107
DOE Contract Number:  
AC02-06CH11357
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biopolymers; Journal Volume: 104; Journal Issue: 6
Country of Publication:
United States
Language:
ENGLISH
Subject:
PLk1; polo kinase; polo-box domain; crystal structure; cationic dialkyl histidine; peptide macrocycles; phosphopeptides

Citation Formats

Qian, Wen-Jian, Park, Jung-Eun, Grant, Robert, Lai, Christopher C., Kelley, James A., Yaffe, Michael B., Lee, Kyung S., and Burke, Terrence R. Neighbor-directed histidine N(τ) alkylation. A route to imidazolium-containing phosphopeptide macrocycles. United States: N. p., 2015. Web. doi:10.1002/bip.22698.
Qian, Wen-Jian, Park, Jung-Eun, Grant, Robert, Lai, Christopher C., Kelley, James A., Yaffe, Michael B., Lee, Kyung S., & Burke, Terrence R. Neighbor-directed histidine N(τ) alkylation. A route to imidazolium-containing phosphopeptide macrocycles. United States. doi:10.1002/bip.22698.
Qian, Wen-Jian, Park, Jung-Eun, Grant, Robert, Lai, Christopher C., Kelley, James A., Yaffe, Michael B., Lee, Kyung S., and Burke, Terrence R. Tue . "Neighbor-directed histidine N(τ) alkylation. A route to imidazolium-containing phosphopeptide macrocycles". United States. doi:10.1002/bip.22698.
@article{osti_1228107,
title = {Neighbor-directed histidine N(τ) alkylation. A route to imidazolium-containing phosphopeptide macrocycles},
author = {Qian, Wen-Jian and Park, Jung-Eun and Grant, Robert and Lai, Christopher C. and Kelley, James A. and Yaffe, Michael B. and Lee, Kyung S. and Burke, Terrence R.},
abstractNote = {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. These cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Furthermore, neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts.},
doi = {10.1002/bip.22698},
journal = {Biopolymers},
number = 6,
volume = 104,
place = {United States},
year = {Tue Jul 07 00:00:00 EDT 2015},
month = {Tue Jul 07 00:00:00 EDT 2015}
}