Flow Chemistry System for Carbohydrate Analysis by Rapid Labeling of Saccharides after Glycan Hydrolysis

    • Wei-Ting Hung1
    • Yi-Ting Chen1
    • Chung-Hsuan Chen1
    • Yuan Chuan Lee2
    • Jim-Min Fang1, 3
    • Wen-Bin Yang1
    • 1The Genomics Research Center, Academia Sinica, Taipei
    • 2Department of Biology, Johns Hopkins University, Baltimore, MD, USA
    • 3Department of Chemistry, National Taiwan University, Taipei

    This study demonstrates the utilization of a flow chemistry system for continuous glycan hydrolysis and saccharide labeling to assist with the existing methods in glycan structural analysis. Acidic hydrolysis of glycans could be accelerated in a flow system. Aldoses and α-ketoacid-type saccharides were effectively labeled with naphthalene-2,3-diamine (NADA) at 60 °C for 10 min to form the fluorescent naphthimidazole (NAIM) and quinoxalinone (QXO) derivatives, respectively. The NADA-labeled derivatives improved the structural determination and composition analysis for their parent saccharides by using matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), liquid chromatography mass spectrometry (LC-MS), and nuclear magnetic resonance (NMR). Furthermore, this protocol was applied to determine the SA–Gal–Glc sequence of GM3-sugar out of six possible permutations.

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