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Determination of the structure of partially methylated sugars as O ‐trimethylsilyl ethers by gas chromatography‐mass spectrometry
Author(s) -
Matsubara Toshiko,
Hayashi Akira
Publication year - 1974
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.1200010113
Subject(s) - trimethylsilyl , chemistry , mass spectrum , mass spectrometry , gas chromatography , methyl group , gas chromatography–mass spectrometry , chromatography , medicinal chemistry , organic chemistry , group (periodic table)
The separation and structural determination of ten partially methylated methyl glucosides by gas chromatography and gas chromatography‐mass spectrometry are described. These glucosides were four possible structures for methyl tri‐ O ‐methylglucosides and six for methyl di‐ O ‐methylglucosides. The positions of free hydroxyl groups in four isomers of methyl tri‐ O ‐methylglucosides could be fairly distinguished from each other by their mass spectra. Mass spectra of methyl di‐ O ‐methylglucosides were similar to each other, though their spectra were different from those of fully methylated or methyl tri‐ O ‐methylglucosides. After introduction of a trimethylsilyl group to the free hydroxyl group, mass spectra of methyl di‐ O ‐methylglucosides showed a characteristic pattern for the position of the trimethylsilylated hydroxyl group, and O ‐trimethylsilyl ethers of methyl tri‐ O ‐methylglucosides also showed distinguishable mass spectra. The structures of fragment ions of partially methylated methyl glucosides were confirmed by high resolution mass spectrometry.