Use of diagnostic neutral losses for structural information on unknown aromatic metabolites: an experimental and theoretical study

Rapid Communications in Mass Spectrometry : RCM
Sophie Bourcier, Yannik Hoppilliard

Abstract

This work presents the use of neutral losses (NL) for the identification of compounds related to the metabolism of tyrosine. The mass spectra of all the studied compounds, recorded at several collision energies, are compared. The fragmentation mechanism of protonated molecules, MH(+), is explained by combining collision-induced dissociation (CID) mass spectra and density functional theory (DFT) calculations. The results show that the first fragmentation is the elimination from MH(+) of a neutral molecule including a functional group of the linear chain. Three primary neutral losses are observed: 17 u (NH(3)), 18 u (H(2)O) and 46 u (H(2)O+CO) characterizing amino, hydroxyl and carboxylic functions on the linear chain. The presence and abundance of ions corresponding to these losses are dependent on (i) the position of the functional group on the linear chain, (ii) the initial localisation of the protonating hydrogen, and (iii) the substitution of the aromatic ring. For compounds including a functional group on the benzylic carbon atom, the investigation of the other functions requires the knowledge of secondary fragmentations. Among these secondary fragmentations we have retained the loss of NH(3) from [MH-18u](+) and the loss o...Continue Reading

References

Nov 1, 2002·Pediatric Research·Jochen MeyburgErtan Mayatepek
Nov 12, 2002·Brazilian Journal of Medical and Biological Research = Revista Brasileira De Pesquisas Médicas E Biológicas·J H Osorio, M Pourfarzam
Oct 8, 2005·Organic & Biomolecular Chemistry·Hadi Lioe, Richard A J O'Hair
Mar 31, 2006·Rapid Communications in Mass Spectrometry : RCM·Sophie BourcierYannik Hoppilliard

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Citations

Mar 23, 2010·Journal of Chromatography. a·Michal HolcapekMiroslav Lísa
Apr 3, 2012·Rapid Communications in Mass Spectrometry : RCM·Ivana StolićMiroslav Bajić
Mar 10, 2010·Rapid Communications in Mass Spectrometry : RCM·Patricia WrightFrank Pullen
Dec 6, 2014·Journal of Mass Spectrometry : JMS·Ondřej KurkaPetr Bednář
Dec 15, 2010·Physical Chemistry Chemical Physics : PCCP·Anita LagutschenkovOtto Dopfer
Jul 28, 2019·Rapid Communications in Mass Spectrometry : RCM·Chukwunonso K NwabufoEd S Krol
Sep 12, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anita KecskemétiAndrás Szekeres
Feb 4, 2011·Bioanalytical Reviews·Tobias Kind, Oliver Fiehn
Nov 26, 2010·The Journal of Physical Chemistry. a·Anita LagutschenkovOtto Dopfer
Dec 25, 2010·Analytical Chemistry·Florian RascheSebastian Böcker

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