skip to main content

SciTech ConnectSciTech Connect

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

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.
 [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:
OSTI Identifier:
DOE Contract Number:
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biopolymers; Journal Volume: 104; Journal Issue: 6
Research Org:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org:
Country of Publication:
United States
PLk1; polo kinase; polo-box domain; crystal structure; cationic dialkyl histidine; peptide macrocycles; phosphopeptides