Anthranilic Acid as a Versatile Fluorescent Tag and Linker for Functional Glycomics

Bioconjug Chem. 2018 Nov 21;29(11):3847-3855. doi: 10.1021/acs.bioconjchem.8b00678. Epub 2018 Nov 12.

Abstract

The advancement of glycoscience is critically dependent on the access to a large number of glycans for their functional study. Naturally occurring glycans are considered a viable source for diverse and biologically relevant glycan libraries. A mixture of free reducing glycans released from natural sources can be fluorescently tagged and separated by chromatography to produce a natural glycan library. Anthranilic acid (AA) has been widely used to fluorescently tag reducing glycans for HPLC or LC/MS analysis. However, AA conjugated glycans are not efficiently immobilized on microarray slides due to the lack of a primary alkylamine functional group. In this study, we have developed simple and efficient chemistry for bioconjugation and further functionalization of glycan-AA conjugates. This new approach enables quick preparation of glycan microarrays and neoglycoproteins from glycan-AA conjugates, which can be separated by weak anion exchange (WAX) and C18 reversed-phase HPLC.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Chickens
  • Chromatography, High Pressure Liquid / methods
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Glycomics / methods*
  • Glycoproteins / chemical synthesis
  • Glycoproteins / chemistry
  • Microarray Analysis
  • Polysaccharides / analysis
  • Polysaccharides / chemical synthesis
  • Polysaccharides / chemistry*
  • Tandem Mass Spectrometry / methods
  • ortho-Aminobenzoates / chemical synthesis
  • ortho-Aminobenzoates / chemistry*

Substances

  • Fluorescent Dyes
  • Glycoproteins
  • Polysaccharides
  • ortho-Aminobenzoates
  • anthranilic acid