A new naphthimidazole derivative for saccharide labeling with enhanced sensitivity in mass spectrometry detection

A series of saccharides, including maltoheptose, blood type B antigen, pullulan and the glucan of Ganoderma lucidum, are easily converted into the naphthimidazole (NAIM) derivatives in high yields by the iodine-promoted oxidative condensation. The NAIM-labeled saccharides, without further purification, show enhanced signals in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS). The combined use of NAIM derivatization and MALDI-TOFMS analysis thus provides a rapid method for identification of saccharides even in less than 1 pmol of saccharide in the sample. Characterization of the biologically active saccharides and complex polysaccharides is also achieved through the NAIM-derivatization method. This study can be further applied to facilitate the isolation and analysis of novel saccharides.