Identification of Sialic Acid and Related Acids as Acetylated Lactones by Gas Chromatography/Mass Spectrometry

✍ Scribed by Nygren, Yvonne; Fredriksson, Sten-Åke; Nilsson, Bo

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 644 KB
• Volume: 31
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(199603)31:3<267::aid-jms306>3.0.co;2-l

✦ Synopsis

A procedure for characterization of sialic acid-like monosaccharides, i.e. 3deoxy-2-ulosonic acids, by gas chromatography/mass spectrometry is described. The free monosaccharides were reduced with NaBH, 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 d e o x y -D -m a n n ~2 -o c t u l ~o ~ acid and 3-deOXy-D-glyCerO-D-galaCtO-2-nOnU~OSO~C 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.