Synthesis of an NDPK phosphocarrier domain peptide containing a novel triazolylalanine analogue of phosphohistidine using click chemistry

Org Lett. 2011 Oct 21;13(20):5604-7. doi: 10.1021/ol202333u. Epub 2011 Sep 22.

Abstract

Click phosphorylation of a propargylated unprotected peptide and phosphoryl azide using chaotrope-assisted Cu(I)-catalyzed 1,3-dipolar cycloaddition enabled a high-yielding and rapid synthesis of a nucleoside diphosphate kinase (NDPK) phosphocarrier domain. The synthesis showcases a valuable synthetic platform for the synthesis of biologically relevant phosphopeptide analogues.

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Catalysis
  • Click Chemistry*
  • Histidine / analogs & derivatives*
  • Histidine / chemistry
  • Molecular Structure
  • Nucleoside-Diphosphate Kinase / chemistry*
  • Nucleoside-Diphosphate Kinase / metabolism
  • Peptides / chemical synthesis*
  • Peptides / metabolism

Substances

  • Peptides
  • Histidine
  • Nucleoside-Diphosphate Kinase
  • Alanine
  • phosphohistidine