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...

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Bibliographic Details
Published in:Biopolymers 2015-11, Vol.104 (6), p.663-673
Main 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.
Format: Article
Language:English
Subjects:
Alkylation
Biology
Biopolymers
Cationic
cationic dialkyl histidine
crystal structure
Crystallography, X-Ray
Formations
Histidine
Histidine - chemistry
Imidazoles - chemistry
Macrocyclic compounds
Macrocyclic Compounds - chemistry
peptide macrocycles
peptide macrocycles, phosphopeptides
Peptides
phosphopeptides
Phosphopeptides - chemistry
PLk1
polo kinase
polo-box domain
Residues
Strategy
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Summary: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. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 663–673, 2015.
ISSN:0006-3525
1097-0282
1097-0282
DOI:10.1002/bip.22698