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Tagging N ‐Linked Glycan with 2,3‐Naphthalenediamine for Mass Spectrometric Analysis
Author(s) -
Hung WeiTing,
Wang ShwuHuey,
Chen CheinHung,
Chen ChungHsuan,
Fang JimMin,
Yang WenBin
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201300253
Subject(s) - chemistry , glycan , mass spectrometry , chromatography , derivatization , quadrupole ion trap , protonation , glycomics , ion trap , ion , biochemistry , organic chemistry , glycoprotein
An expedient conversion of N ‐glycans to the naphthimidazole (NAIM) derivatives is established by the iodine‐promoted oxidative condensation of N ‐glycans with 2,3‐naphthalenediamine at room temperature. The NAIM derivatization not only introduces a UV/fluorescence sensitive chromophore but also increases the hydrophobicity of N ‐glycans to improve the ionization efficiency in mass spectrometry (MS). Thus, the NAIM derivatives of N ‐linked oligosaccharide Man9 and tetra‐antennary N ‐glycan NA4 show enhanced sodiated ions in matrix‐assisted laser desorption/ionization time‐of‐flight MS with a detection limit of 50 pmol, whereas the NAIM derivative of sialic acid‐containing tri‐antennary N ‐glycan A3 is detected as the protonated ion by linear trap quadrupole Fourier transform MS. Furthermore, the N ‐glycans of ovalbumin and fetuin are released and directly converted to the NAIM derivatives for facilitated HPLC and MS analyses. This is the first study of N ‐glycan‐NAIM for MS measurement, which is especially valuable in glycan analysis of biological samples containing sensitive subunits.