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Identification of Sialic Acid and Related Acids as Acetylated Lactones by Gas Chromatography/Mass Spectrometry
Author(s) -
Nygren Yvonne,
Fredriksson StenÅke,
Nilsson Bo
Publication year - 1996
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199603)31:3<267::aid-jms306>3.0.co;2-l
Subject(s) - chemistry , monosaccharide , mass spectrometry , chromatography , fast atom bombardment , gas chromatography , sialic acid , fragmentation (computing) , gas chromatography–mass spectrometry , electron ionization , tandem mass spectrometry , chemical ionization , organic chemistry , biochemistry , ionization , ion , computer science , operating system
A procedure for characterization of sialic acid‐like monosaccharides, i.e. 3‐deoxy‐2‐ulosonic acids, by gas chromatography/mass spectrometry is described. The free monosaccharides were reduced with NaBH 4 and the resulting 3‐deoxyaldonic acids were acetylated. Five‐membered ring lactones were obtained as the major products. The keto‐deoxy compounds N ‐acetylneuraminic acid, N ‐glycolylneuraminic acid, 3‐deoxy‐D‐manno‐2‐octulosonic acid and 3‐deoxy‐D‐glycero‐D‐galacto‐2‐nonulosonic acid were investigated. A detailed study of the electron impact ionization fragmentation pathways of the acetylated lactones were conducted using tandem mass spectrometry. The mass spectra allowed unambiguous structural identification of the acidic monosaccharides.