Oxidation of mannosyl oligosaccharides by hydroxyl radicals as assessed by electrospray mass spectrometry
authors Tudella, J; Nunes, FM; Paradela, R; Evtuguin, DV; Domingues, P; Amado, F; Coimbra, MA; Barros, AIRNA; Domingues, MRM
nationality International
journal CARBOHYDRATE RESEARCH
author keywords Oligosaccharides; Oxidation; Electrospray ionization mass spectrometry; Galactomannans; Hydroxyl radical
keywords AQUEOUS-SOLUTION; STRUCTURAL-CHARACTERIZATION; RADIATION-CHEMISTRY; PEROXYL RADICALS; HYALURONIC-ACID; IDENTIFICATION; DEGRADATION; POLYSACCHARIDES; PRODUCTS; SCISSION
abstract The hydroxyl radicals are widely implicated in oxidation of carbohydrates during biological and industrial processes being responsible for their structural modifications and causing functional damage. The identification of intermediate oxidation products is hampered by a lack of reliable sensible methods for their detection. In this study, the oxidation of two models of galactomannans (Man(3) and GalMan(2)) has been studied in reaction with hydroxyl radical generated by Fenton reaction. The oxidation patterns were assessed using preparative ligand-exchange/size-exclusion chromatography (LEX/SEC) coupled with tandem electrospray mass spectrometry (ESI-MS/MS). This allowed the identification of derived oligosaccharides (OS) containing hexuronic, hexonic, pentonic and erythronic acid residues and neutral OS bearing hydroperoxy, hydrated carbonyl moieties and residues from pyranosyl ring cleavage. The depolymerization products have been also detected upon oxidation of oligomers. This study allowed developing a simple, effective 'fingerprinting' protocol for detecting the damage done to mannans by oxidative radicals. (C) 2011 Elsevier Ltd. All rights reserved.
publisher ELSEVIER SCI LTD
issn 0008-6215
year published 2011
volume 346
issue 16
beginning page 2603
ending page 2611
digital object identifier (doi) 10.1016/j.carres.2011.09.011
web of science category Biochemistry & Molecular Biology; Chemistry, Applied; Chemistry, Organic
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000297188900011
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