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Characterization of the glycosidic linkage of underivatized disaccharides by interaction with Pb2+ ions

✍ Scribed by Ahlam El Firdoussi; Marie Lafitte; Jeanine Tortajada; Omar Kone; Jean-Yves Salpin

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 308 KB
Volume: 42
Category: Article
ISSN: 1076-5174
DOI: 10.1002/jms.1220

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✦ Synopsis

Abstract

Electrospray ionization in combination with tandem mass spectrometry and lead cationization is used to characterize the linkage position of underivatized disaccharides. Lead(II) ions react mainly with disaccharides by proton abstraction to generate [Pb(disaccharide)~m~− H]^+^ ions (m = 1–2). At low cone voltages, an intense series of doubly charged ions of general formula [Pb(disaccharide)~n~]^2+^ are also observed. Our study shows that MS/MS experiments have to be performed to differentiate Pb^2+^‐coordinated disaccharides. Upon collision, [Pb(disaccharide) − H]^+^ species mainly dissociate according to glycosidic bond cleavage and cross‐ring cleavages, leading to the elimination of C~n~H~2__n__~O~n~ neutrals (n = 2–4). The various fragmentation processes allow the position of the glycosidic bond to be unambiguously located. Distinction between glc‐glc and glc‐fru disaccharides also appears straightforward. Furthermore, for homodimers of D‐glucose our data demonstrate that the anomericity of the glycosidic bond can be characterized for the 1 → n linkages (n = 2, 4, 6). Consequently, Pb^2+^ cationization combined with tandem mass spectrometry appears particularly useful to identify underivatized disaccharides. Copyright © 2007 John Wiley & Sons, Ltd.

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