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Decomposition of N ‐hydroxylated compounds during atmospheric pressure chemical ionization
Author(s) -
Eichenberger Silvan,
Méret Michaël,
Bienz Stefan,
Bigler Laurent
Publication year - 2010
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1703
Subject(s) - chemistry , atmospheric pressure chemical ionization , chemical ionization , derivative (finance) , mass spectrometry , decomposition , polyamine , chromatography , amine gas treating , analyte , ionization , electrospray ionization , organic chemistry , ion , biochemistry , financial economics , economics
Abstract N ‐Hydroxylated polyamine derivatives were found to decompose during the ionization process of liquid chromatography‐atmospheric pressure chemical ionization‐mass spectrometry (LC‐APCI‐MS) experiments. The phenomenon was studied with a model compound, a synthetic N ‐hydroxylated tetraamine derivative. It was found that reduction, oxidation and water elimination occurred during APCI to generate the corresponding amine, N ‐oxide, and imine. The investigation further revealed that decomposition of hydroxylamines during APCI depends upon the concentration of the analyte and on the acidity of the solution introduced into the ionization source. The pH‐dependence of decomposition was utilized for the development of an MS method that allows for the unambiguous identification of NOH functionalities. This method was applied for the study of natural products including polyamine toxins from the venom of the spider Agelenopsis aperta and mayfoline, a cyclic polyamine derivative of the shrub Maytenus buxifolia . Copyright © 2009 John Wiley & Sons, Ltd.