Positive-ion ESI mass spectrometry of regioisomeric nonreducing oligosaccharide fatty acid monoesters: in-source fragmentation of sodium adducts

Journal of Mass Spectrometry : JMS
Ignacio Pérez-VictoriaJuan Carlos Morales

Abstract

Structural characterization and differentiation of a novel group of regioisomeric monolaurate esters of the nonreducing trisaccharides raffinose and melezitose, and the nonreducing tetrasaccharide stachyose has been obtained using positive electrospray ionization (ESI) mass spectrometry with in-source fragmentation. The surfactant nature and high polarity of these compounds make them appropriate analytes for being studied by conventional ESI-MS. The position of the acyl chain in each particular regioisomer has been used as a reporter group that allows unambiguous rationalization of the fragmentation routes of the corresponding natriated molecular ions [M + Na](+). In all cases, the main fragment ions were produced through cleavage of the glycosidic bond involving two anomeric carbons, the C-1' and C-2'' of the alpha-D-Glcp-(1-2)-beta-D-Fruf bond, and it was observed that sodium cation retention occurred on the heavier mass fragment of the two formed fragments, (e.g. di- or trisaccharide type vs monosaccharide type). Our results may help to better understand the fragmentation behavior of nonreducing oligosaccharides (as sodium adducts) in positive ESI mass spectrometry.

References

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May 1, 1993·Biological Mass Spectrometry·C G de KosterJ Haverkamp
Aug 18, 1999·Analytical Chemistry·M T CancillaC B Lebrilla
Sep 14, 2000·Journal of Colloid and Interface Science·G GarofalakisD B Sarney
Apr 6, 2004·Carbohydrate Research·Kumari S DevulapalleFrancisco J Plou
Aug 19, 2004·Mass Spectrometry Reviews·Valérie Gabelica, Edwin De Pauw
Jan 8, 2005·Biotechnology and Applied Biochemistry·Manuel FerrerAntonio Ballesteros
Dec 13, 2006·Carbohydrate Research·Ignacio Pérez-VictoriaJuan Carlos Morales

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Citations

Dec 7, 2010·Biochimica Et Biophysica Acta·Ignacio Pérez-VictoriaJosé M Pérez-Victoria

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