The total chemical synthesis of the monoglycosylated GM2 ganglioside activator using a novel cysteine surrogate

Chem Commun (Camb). 2015 Jun 21;51(49):9946-8. doi: 10.1039/c5cc02967h.

Abstract

We describe a novel peptide ligation/desulfurization strategy using a β-mercapto-N-glycosylated asparagine derivative. The newly developed procedure was successfully applied to the total chemical synthesis of the GM2 ganglioside activator protein bearing a monosaccharide on the native glycosylation site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Chemistry Techniques, Synthetic
  • Cysteine*
  • G(M2) Activator Protein / chemical synthesis*
  • G(M2) Activator Protein / chemistry*
  • Glycosylation
  • Models, Molecular
  • Molecular Sequence Data
  • Monosaccharides / chemistry
  • Protein Conformation

Substances

  • G(M2) Activator Protein
  • Monosaccharides
  • Cysteine