Mass-spectral studies of isomeric D-ribofuranosylribitol disaccharides from the capsular polysaccharides of Haemophilus influenzae type b and Escherichia coli K 100.
Two isomeric-D-ribofuranosylribitols, derived from capsular polysaccharides of Haemophilus influenzae type b and Escherichia coli K 100, were methylated or acetylated, and the products analyzed by gas-liquid chromatography-mass spectrometry. The marked difference in the mass spectra of the methyl ethers of these disaccharides allowed clear distinction between 1- and 2-O-D-ribofuranosylribitol was characteristic for this disaccharide; its isomer, the (1 leads to 2)-linked species, has a base peak at m/e 57. The difference in the base peaks is attributable to fragmentation of the methylated ribitol, as both spectra display common ions characteristic of the methylated D-ribofuranosyl group. For the acetylated disaccharides, the mass spectra displayed common ions characteristic of the acetylated D-ribofuranosyl group. However, no ions similar to those found for the methylated ribitol allowed ready differentiation between the two acetates. Instead, their spectra displayed similar ions, differing somewhat in relative abundance; the M-1 ion, m/e 577, was obtained for both. Comparison of the relative abundance of m/e 139, 259, and 303 in the spectra of the two acetates did allow distinction between them.
D002849:Chromatography, Gas; D004187:Disaccharides / Q000032:analysis*; D004926:Escherichia coli / Q000276:immunology*; D006193:Haemophilus influenzae / Q000276:immunology*; D007536:Isomerism; D013058:Mass Spectrometry; D011135:Polysaccharides, Bacterial / Q000032:analysis*; D012255:Ribitol / Q000032:analysis; D012266:Ribose / Q000032:analysis
D004187:Disaccharides; D011135:Polysaccharides, Bacterial; D012255:Ribitol; D012266:Ribose