5-hydroxymethylfuraldehyde (5-HMF) and simpler compounds, such as levulinic acid (LA) and glyceraldehyde, are platform molecules produced by the thermal acid-catalyzed dehydration of carbohydrates coming from biomass. Understanding sugar degradation pathways on a molecular level is necessary to increase selectivity, reduce degradation by-products yields and optimize catalytic strategies, fundamental knowledge for the development of a sustainable renewable industry. In this work gaseous protonated D-fructose ions, generated in the ESI source of a triple quadrupole mass spectrometer, were allowed to undergo Collisionally Activated Decomposition (CAD) into the quadrupole collision cell. The ionic intermediates and products derived from protonated D-fructose dehydration were structurally characterized by their fragmentation patterns and the relative water-loss dehydration energies measured by energy-resolved CAD mass spectra. The data were compared with those obtained from protonated Dglucose decomposition in the same experimental conditions. In the gas phase, D-fructose dehydration leads to the formation of a mixed population of isomeric [C6H6O3]Hþ ions, whose structures do not correspond exclusively to 5-hydroxymethyl-2-furaldehyde protonated at the more basic aldehydic group.

A mass spectrometric study of the acid-catalysed d-fructose dehydration in the gas phase / Pepi, Federico; Ricci, Andreina; Garzoli, Stefania; Troiani, Anna; Salvitti, Chiara; Di Rienzo, Brunella; Giacomello, Pierluigi. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - STAMPA. - 413:(2015), pp. 145-150. [10.1016/j.carres.2015.05.013]

A mass spectrometric study of the acid-catalysed d-fructose dehydration in the gas phase

PEPI, Federico
;
GARZOLI, STEFANIA;TROIANI, Anna;SALVITTI, CHIARA;GIACOMELLO, Pierluigi
2015

Abstract

5-hydroxymethylfuraldehyde (5-HMF) and simpler compounds, such as levulinic acid (LA) and glyceraldehyde, are platform molecules produced by the thermal acid-catalyzed dehydration of carbohydrates coming from biomass. Understanding sugar degradation pathways on a molecular level is necessary to increase selectivity, reduce degradation by-products yields and optimize catalytic strategies, fundamental knowledge for the development of a sustainable renewable industry. In this work gaseous protonated D-fructose ions, generated in the ESI source of a triple quadrupole mass spectrometer, were allowed to undergo Collisionally Activated Decomposition (CAD) into the quadrupole collision cell. The ionic intermediates and products derived from protonated D-fructose dehydration were structurally characterized by their fragmentation patterns and the relative water-loss dehydration energies measured by energy-resolved CAD mass spectra. The data were compared with those obtained from protonated Dglucose decomposition in the same experimental conditions. In the gas phase, D-fructose dehydration leads to the formation of a mixed population of isomeric [C6H6O3]Hþ ions, whose structures do not correspond exclusively to 5-hydroxymethyl-2-furaldehyde protonated at the more basic aldehydic group.
2015
5-Hydroxymethylfuraldehyde; biomass; fructose dehydration; gas phase; mass spectrometry; biochemistry; analytical chemistry; organic chemistry
01 Pubblicazione su rivista::01a Articolo in rivista
A mass spectrometric study of the acid-catalysed d-fructose dehydration in the gas phase / Pepi, Federico; Ricci, Andreina; Garzoli, Stefania; Troiani, Anna; Salvitti, Chiara; Di Rienzo, Brunella; Giacomello, Pierluigi. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - STAMPA. - 413:(2015), pp. 145-150. [10.1016/j.carres.2015.05.013]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/800055
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