MgI2 -chemoselective cleavage for removal of amino acid protecting groups: A fresh vision for peptide synthesis

Biopolymers. 2017 Mar;108(2). doi: 10.1002/bip.22908.

Abstract

In the field of peptide synthesis, the key to a successful access to synthetic targets lies on a pertinent combination of protecting groups. Their choice is directed by their selective removal conditions. We present here the behavior of some of the most used protecting groups in peptide chemistry under experimental cleavage conditions, combining MgI2 with MW irradiation, using 2-Me-THF as a green solvent. In these experimental conditions, the benzyloxycarbonyl protecting group as well as the Merrifield resin can be re-considered in peptide chemistry.

Keywords: amino acids; chemoselective cleavage; magnesium iodide; protecting groups; solid phase peptide synthesis.

MeSH terms

  • Amino Acids / chemistry*
  • Chromatography, High Pressure Liquid
  • Esters / chemistry
  • Furans / chemistry
  • Iodides / chemistry*
  • Magnesium Compounds / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Chemical
  • Molecular Structure
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • Solid-Phase Synthesis Techniques / methods*
  • Solvents / chemistry

Substances

  • 2-me-tetrahydrofuran
  • Amino Acids
  • Esters
  • Furans
  • Iodides
  • Magnesium Compounds
  • Peptides
  • Solvents
  • magnesium iodide