Decomposition of N-hydroxylated compounds during atmospheric pressure chemical ionization

Journal of Mass Spectrometry : JMS
Silvan EichenbergerLaurent Bigler

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 N-OH 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.

References

Dec 18, 2001·Rapid Communications in Mass Spectrometry : RCM·W TongJ E Patrick
Nov 3, 2004·Journal of the American Society for Mass Spectrometry·Manuel TzourosLaurent Bigler
Jun 29, 2005·Toxicon : Official Journal of the International Society on Toxinology·Manuel TzourosLaurent Bigler

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Citations

Aug 17, 2020·Metabolites·Yvonne M ForsterLaurent Bigler

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