Synthesis of Na2S2O4 mediated cleavable affinity tag for labeling of O-GlcNAc modified proteins via azide-alkyne cycloaddition

Bioorg Med Chem Lett. 2021 Sep 15:48:128244. doi: 10.1016/j.bmcl.2021.128244. Epub 2021 Jul 3.

Abstract

A facile and convergent procedure for the synthesis of azobenzene-based probe was reported, which could selectively release interested proteins conducted with sodium dithionite. Besides, the cleavage efficiency is closely associated with the structural features, in which an ortho-hydroxyl substituent is necessary for reactivity. In addition, the azobenzene tag applied in the Ac4GlcNAz-labled proteins demonstrated high efficiency and selectivity in comparison with Biotin-PEG4-Alkyne, which provides a useful platform for enrichment of any desired bioorthogonal proteomics.

Keywords: Cleavable tag; Metabolic labeling; O-GlcNAc; Proteomics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry
  • Acetylglucosamine / metabolism*
  • Alkynes / chemistry
  • Alkynes / metabolism*
  • Azides / chemistry
  • Azides / metabolism*
  • Cycloaddition Reaction
  • Dithionite / chemical synthesis
  • Dithionite / chemistry
  • Dithionite / metabolism*
  • Molecular Structure
  • N-Acetylglucosaminyltransferases / chemistry
  • N-Acetylglucosaminyltransferases / metabolism*
  • Proteomics

Substances

  • Alkynes
  • Azides
  • Dithionite
  • N-Acetylglucosaminyltransferases
  • Acetylglucosamine