Abstract
An anomeric pair of the lysoglyceroganglioside 1-O-octadecyl-3-O-(N-acetyl)neuraminyl-sn-glycerol sodium salt was studied to see if sialic anomers were distinguishable by mass spectra. It was evident that, in the electrospray ionization and fast-atom bombardment product-ion spectra: (1) in the positive MS2 product-ion spectrum, the β- anomer showed an unexpected aglycone-side sodiated sodium alkoxide ion, which was absent for the α-anomer; (2) in both polarities the β-anomer showed dehydration much more easily than the α-anomer; and (3) in the negative MS2 product-ion spectrum, the β-anomer also readily showed decarboxylation. Our hypothesis is that, although several easily interconvertible conformations may be allowed, the one having the large aglycone in the equatorial orientation affects the collision-induced dissociation fragmentations.
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Published online November 6, 2008
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Ohashi, Y., Kubota, M., Hatase, H. et al. Distinction of sialyl anomers on ESI- and FAB-MS/MS: Stereo-specific fragmentations. J Am Soc Mass Spectrom 20, 394–397 (2009). https://doi.org/10.1016/j.jasms.2008.10.020
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DOI: https://doi.org/10.1016/j.jasms.2008.10.020