A divergent strategy for attaching polypyridyl ligands to peptides

J Org Chem. 2010 Feb 5;75(3):650-9. doi: 10.1021/jo9021953.

Abstract

A divergent method for incorporating polypyridyl ligands into peptides is reported. Three N-Fmoc unnatural amino acids (1-3) that contain varying linkers between the alpha-carbon and a 2-(hydroxymethyl)pyridyl group were synthesized in enantioenriched form. These amino acids were used as anchors for incorporating multidentate ligands onto a peptide chain in a site-specific fashion. Multiple peptide-ligand conjugates were synthesized from single precursors by solution- or solid-phase methods. Peptides containing more than one metal-binding unit can be produced by this method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Metals / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Protein Folding
  • Pyridines / chemistry*
  • Solutions

Substances

  • Amino Acids
  • Ligands
  • Metals
  • Organometallic Compounds
  • Peptides
  • Pyridines
  • Solutions