Neighbor‐directed histidine N (τ)–alkylation: A route to imidazolium‐containing phosphopeptide macrocycles
Year: 2015
Type: article
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.
Source: Biopolymers
DOI: 10.1002/bip.22698
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: green
Awards: G102163711, G1120028786, Systems Biology of cell Decision Processes, Protein Kinase Signaling and Cell Cycle Control, G5384392517, Applications of New Mass Spectral Techniques, G6350445350, G6374948078, G81286254, G9000038451, G9000180872, G9000303978, G9000330576, G9000350259, G9000352409, Inhibitors of Tyrosine Kinase-Dependent Signaling as Anti-Cancer Agents, G951986024
OpenAlex ID: W1960192223