The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

Chem Commun (Camb). 2017 Feb 23;53(17):2634-2636. doi: 10.1039/c6cc10203d.

Abstract

A novo trifunctional EDTA-like peptidomimetic amino acid is described. This unique building block, which is prepared in a straightforward manner from commercialized starting materials, contains three moieties: a hexadentate chelating unit similar to that present in EDTA, and amino and carboxylic groups, which facilitate its introduction into the backbone of peptides using conventional SPPS. As a proof of concept, this building block is introduced into a cyclic peptide inspired from the family of Gratisin analogues. The designed peptide contains the amino acid analogue in one of the turns, and chelates Ca2+ with nanomolar affinity at physiological pH.

MeSH terms

  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • Chelating Agents / chemical synthesis*
  • Chelating Agents / chemistry
  • Edetic Acid / chemistry*
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptidomimetics / chemical synthesis*
  • Peptidomimetics / chemistry

Substances

  • Amino Acids
  • Chelating Agents
  • Peptides
  • Peptidomimetics
  • Edetic Acid