Abstract
High-resolution mass spectrometry has become another valuable tool for characterization of simple and complex glycosides. The method is based on the collision of a high-energy electron against a sample under study producing as result a cation radical fragment known as the molecular ion, which should match with the molecular weight of the molecule. The mass spectrum also registers a number of fragments with the most intense base peak assigned a relative intensity of 100. Mass spectrometry can be applied as high and low ionization experiments, the former the most suitable for glycosides electron impact and the latter for fast atom bombardment (FAB) and electrospray ionization routine experiments for characterization of glycosides. In terms of sensitivity of the measurement this instrumental method requires a small amount of sample, even in the order of nanogram quantities.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Bieman K (1963) Application of mass spectrometry to structure problems. XIV. 1. Acetates of partially methylated pentoses and hexoses. J Am Chem Soc 85:2289–2294
Brito-Arias M, Pereda-Miranda R, Heathcock CH (2004) Synthesis of tricolorin F. J Org Chem 69:4567–4570
Harada KI, Suzuki M, Takeda N, Tatematsu A, Kambara H (1982) Molecular secondary ion mass spectra of kanamycins. Org Mass Spectrom 17:247–252
Dell M (1987) F.A.B.-mass spectrometry of carbohydrates. Adv Carbohydr Chem Biochem 45:19–72
Wolfender JL, Maillard M, Marston A, Hostettman K (1992) Mass spectrometry of underivatized naturally occurring glycosides. Pytochem Anal 3:193–214
Morris HR, Thompson MR, Osuga DT, Ahmed AI, Chan SM, Vandenheede JR, Feeney RE (1978) Antifreeze glycoproteins from the blood of an antarctic fish. The structure of the proline-containing glycopeptides. J Biol Chem 253:5155–5162
Dell A, Morris HR (2001) Glycoprotein structure determination by mass spectrometry. Science 291:2351–2356
Teng-umnuay P, Morris HR, Dell A, Panico M, Paxton T, West CM (1998) The cytoplasmic F-box binding protein SKP1 contains a novel pentasaccharide linked to hydroxyproline in Dictyostelium. J Biol Chem 273:18242–18249
Easton RL, Patankar MS, Clark GF, Morris HR, Dell A (2000) Pregnancy-associated changes in the glycosylation of Tamm-Horsfall glycoprotein: expression of sialyl lewisx sequences on core 2 typeo-glycans derived from uromodulin. J Biol Chem 275:21928–21938
Domon B, Costello CE (1988) A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjug J 5:397–409
Spina E, Sturiale L, Romeo D, Impallomeni G, Garozzo D, Waidelich D, Glueckmann M (2004) New fragmentation mechanisms in matrix-assisted laser desorption/ionization time-of-flight/time-of-flight tandem mass spectrometry of carbohydrates. Rapid Commun Mass Spectrom 18:392–398
Maslen SL, Goubet F, Adam A, Dupreeb P, Stephens E (2007) Structure elucidation of arabinoxylan isomers by normal phase HPLC–MALDI-TOF/TOF-MS/MS. Carbohydr Res 342:724–735
Daniel R, Chevolot L, Carrascal M, Tissot B, Moura PAS, Abian J (2007) Electrospray ionization mass spectrometry of oligosaccharides derived from fucoidan of Ascophyllum nodosum. Carbohydr Res 342:826–834
Broberg A (2007) High-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry for analysis of oligosaccharides derivatized by reductive amination and N, N-dimethylation. Carbohydr Res 342:1462–1469
Price NPJ, Ray KJ, Vermillion K, Kuo T-M (2009) MALDI-TOF mass spectrometry of naturally occurring mixtures of monorhamnolipids and dirhamnolipids. Carbohydr Res 344:204–209
von Witzendorff D, Maass K, Pich A, Ebeling S, Kölle S, Kochel C, Ekhlasi-Hundrieser M, Geyer H, Geyer R, Töpfer-Petersen E (2009) Characterization of the acidic N-linked glycans of the zona pellucida of prepuberal pigs by a mass spectrometric approach. Carbohydr Res 344:1541–1549
Guillard M, Gloerich J, Wessels HJCT, Morava E, Wevers RA, Lefeber DJ (2009) Automated measurement of permethylated serum N-glycans by MALDI–linear ion trap mass spectrometry. Carbohydr Res 344:1550–1557
Westphal Y, Kühnel S, Schols HA, Voragen AGJ, Gruppen H (2010) LC/CE–MS tools for the analysis of complex arabino-oligosaccharides. Carbohydr Res 345:2239–2251
Tep S, Hincapie M, Hancock WS (2012) A MALDI-TOF MS method for the simultaneous and quantitative analysis of neutral and sialylated glycans of CHO-expressed glycoproteins. Carbohydr Res 347:121–129
Wuhrer M, de Boer AR, Deelder AM (2009) Structural glycomics using hydrophilic interaction chromatography (HILIC) with mass spectrometry. Mass Spectrom Rev 28:192–206
Harvey DJ (2015) Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009–2010. Mass Spectrom Rev 34:268–422
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Brito-Arias, M. (2016). Mass Spectrometry of Glycosides. In: Synthesis and Characterization of Glycosides. Springer, Cham. https://doi.org/10.1007/978-3-319-32310-7_10
Download citation
DOI: https://doi.org/10.1007/978-3-319-32310-7_10
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-32308-4
Online ISBN: 978-3-319-32310-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)