Fast preparation of an N-acetylglucosaminylated peptide segment for the chemoenzymatic synthesis of a glycoprotein

Org Biomol Chem. 2013 Nov 7;11(41):7199-207. doi: 10.1039/c3ob41565a.

Abstract

A novel GlcNAc-Asn unit carrying trifluoroacetic acid (TFA)-sensitive O-protecting groups was prepared. The unit was used for the solid-phase peptide synthesis (SPPS) of the N-acetylglucosaminylated emmprin (35-69) thioester via one-step deprotection by TFA combined with the N-alkylcysteine thioesterification method. This segment was used for the synthesis of the first Ig domain (22-104) of emmprin carrying GlcNAc by one-pot ligation with other segments using the thioester method. Finally, the sugar chain was elongated by transglycosylation using glycosynthase to give the Ig domain carrying the disialo- and asialo-complex-type sugar chain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucosamine / analogs & derivatives
  • Glucosamine / chemical synthesis*
  • Glucosamine / chemistry*
  • Glycoproteins / biosynthesis*
  • Glycoproteins / chemistry
  • Glycoside Hydrolases / chemistry
  • Glycoside Hydrolases / metabolism*
  • Glycosylation
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry*

Substances

  • Glycoproteins
  • Peptides
  • Glycoside Hydrolases
  • Glucosamine