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Sequence determination of permethylated oligosaccharides by chemical ionization mass spectrometry
Author(s) -
Harada Kenichi,
Ito Susumu,
Takeda Naohito,
Suzuki Makoto,
Tatematsu Akira
Publication year - 1983
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200100103
Subject(s) - chemistry , oxonium ion , glycosidic bond , adduct , mass spectrometry , chemical ionization , molecule , ion , reagent , electrospray ionization , mass spectrum , isobutane , protonation , ionization , organic chemistry , chromatography , enzyme , catalysis
Chemical ionization mass spectra of several permethylated oligosaccharides were studied using isobutane and ammonia as reagent gases. In the molecular ion region, protonated molecule [MH] + or ammonium adduct ion [M·NH 4 ] + were observed. Fragmentations were mainly restricted to the cleavages of the glycosidic bonds between the glycosidic oxygen and the anomeric carbon atoms. Resulting fragment ions were classified into oxonium type ions and their counterpart ions with hydrogen or methyl transfer, which were very useful for determining the sequence of the constituent saccharide units. These ions were confirmed by shift techniques with pertrideuteromethyl derivatives, deuterated reagent gases, i ‐C 4 2 H 10 and N 2 H 3 , and 15 NH 3. Finally, these results were applied successfully to the structural characterization of the unknown trisaccharides, viridotriose A (6), B (7) and C (8).