Regeneration of Free Reducing Glycans from Reductive Amination-Tagged Glycans by Oxone

J Org Chem. 2022 Mar 4;87(5):3736-3740. doi: 10.1021/acs.joc.1c02709. Epub 2022 Feb 10.

Abstract

Glycans are usually fluorescently tagged by reductive amination for analytic tools. However, free reducing glycan regeneration is sometimes important and necessary for further structural or functional studies. Here, we introduce a new method for efficiently removing fluorescent tags from glycoconjugates by a simple treatment with Oxone. This method is proven to be fast and general after being tested on a series of common saccharides and widely used tags. We successfully achieved N-glycopeptide synthesis by using the regenerated glycans.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Glycoconjugates*
  • Polysaccharides* / chemistry
  • Regeneration
  • Sulfuric Acids

Substances

  • Glycoconjugates
  • Polysaccharides
  • Sulfuric Acids
  • potassium peroxymonosulfuric acid