Synthesis of and specific antibody generation for glycopeptides with arginine N-GlcNAcylation

Angew Chem Int Ed Engl. 2014 Dec 22;53(52):14517-21. doi: 10.1002/anie.201407824. Epub 2014 Oct 29.

Abstract

As a unique and unappreciated protein posttranslational modification, arginine N-glycosylation was recently discovered to play an important role in the process that bacteria counteract host defenses. To provide chemical tools for further proteomic and biochemical studies on arginine N-glycosylation, we report the first general strategy for a rapid and cost-effective synthesis of glycopeptides carrying single or multiple arginine N-GlcNAcyl groups. These glycopeptides were successfully utilized to generate the first antibodies that can specifically recognize arginine N-GlcNAcylated peptides or proteins in a sequence-independent manner.

Keywords: N-GlcNAcylation; antibodies; arginine; glycopeptides; solid-phase peptide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibodies / chemistry*
  • Antibodies / metabolism
  • Arginine / chemistry*
  • Escherichia coli Proteins / metabolism
  • Glucosamine / chemistry*
  • Glycopeptides / chemistry*
  • Glycosylation
  • Silver / chemistry
  • Solid-Phase Synthesis Techniques
  • Virulence Factors / metabolism

Substances

  • Antibodies
  • Escherichia coli Proteins
  • Glycopeptides
  • NleB protein, E coli
  • Virulence Factors
  • Silver
  • Arginine
  • Glucosamine