Electrospray ionisation tandem mass spectrometric study of hydrogen-bonding interactions of some disaccharides with lysine

Nagaveni, V. ; Prabhakar, S. ; Vairamani, M. (2001) Electrospray ionisation tandem mass spectrometric study of hydrogen-bonding interactions of some disaccharides with lysine Rapid Communications in Mass Spectrometry, 15 (12). pp. 1017-1021. ISSN 0951-4198

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/rcm.333...

Related URL: http://dx.doi.org/10.1002/rcm.333

Abstract

The efficiency of formation of protonated heterotrimers of lysine with underivatised sugars (mono-, di-, and trisaccharides) and N-acetylglucosamine (N-AcGlc) was studied under electrospray ionisation conditions. The collision induced dissociation spectra of [Lys+ sugar+ NAcGlc + H]+ resulted in [Lys + NAcGlc + H]+ and [Lys + sugar + H]+ as the major product ions. Relative abundances of these two fragments reflect the extent of adduct formation of protonated lysine plus sugar, with reference to the reference compound NAcGlc. This relative abundance ratio was found to be characteristic of the sugar structure. In this way it was observed that the ability of lysine to form a protonated heterodimer with neutral sugars increases with an increase in the number of acetal oxygens. Lactose showed an anomalously high affinity for protonated Lys, possibly reflecting the axial hydroxyl at C4. The postulated involvement of the ∓-NH2 group of lysine in the formation of protonated heterodimers with sugars was supported by similar results of similar experiments with NH3 in place of lysine.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons.
ID Code:55105
Deposited On:18 Aug 2011 12:12
Last Modified:18 Aug 2011 12:12

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