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Fast‐atom bombardment mass spectrometric study of some N‐ and S‐glycosides of acetylated hexose isomers
Author(s) -
Liptáak Miklós,
Heerma Wigger
Publication year - 1993
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290070726
Subject(s) - chemistry , fast atom bombardment , hexose , protonation , monosaccharide , mass spectrometry , acetic acid , glycoside , mass spectrum , ion , alkyl , molecule , aryl , medicinal chemistry , stereochemistry , organic chemistry , chromatography , enzyme
Various N ‐aryl, S ‐aryl and S ‐alkyl glycosides of acetylated D‐glucose, D‐galactose and D‐mannose have been studied by fast‐atom bombardment mass spectrometry. It was found that the matrix used has a considerable effect on the relative peak intensities in the molecular mass region. Glycerol apparently promotes the formation of protonated molecules (MH + ) whereas in 3‐nitrobenzyl alcohol both MH + ions and M + · radical cations are abundant. The unimolecular decomposition spectra of the MH + ions exhibit two significant peaks corresponding to losses of acetic acid and of the aglycon. The intensity ratios of these fragment ions are dependent on the nature of the aglycon and the hexose unit and can be used to identify the monosaccharides. It has also been established that acetic acid elimination occurs mainly from the C‐3 position.