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Electrospray tandem mass spectrometry of aminochromes
Author(s) -
LemosAmado Francisco,
Domingues Pedro,
FerrerCorreia A.,
Remião Fernando,
Milhazes Nuno,
Borges Fernanda,
Carvalho Félix D.,
Bastos Maria L.
Publication year - 2001
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.498
Subject(s) - chemistry , electrospray , tandem mass spectrometry , fragmentation (computing) , mass spectrometry , formic acid , chromatography , protonation , organic chemistry , ion , computer science , operating system
The catecholamines adrenaline, noradrenaline, dopamine, dopa and isoprenaline were oxidized into their respective aminochromes: adrenochrome, noradrenochrome, dopaminochrome, dopachrome and isoprenochrome. Tandem mass spectrometry (MS/MS) fragmentation patterns were examined for the five aminochromes in order to establish a general structural assignment of these oxidation products by electrospray mass spectrometry. Although protonated aminochromes undergo similar fragmentation patterns with a characteristic consecutive loss of two carbonyl groups, the presence of different substituents in the parent compounds led to significant changes in the CID spectra. This feature is more evident for isoprenochrome and dopachrome, especially for the latter where the MS/MS spectrum is dominated by the loss of formic acid. A general pattern of fragmentation for aminochromes is proposed, which should provide a suitable basis to aid their characterization in studies in vivo or in vitro . Copyright © 2001 John Wiley & Sons, Ltd.