Gas-Phase Stability of Negatively Charged Organophosphate Metabolites Produced by Electrospray Ionization and Matrix-Assisted Laser Desorption/Ionization

Gas-Phase Stability of Negatively Charged Organophosphate Metabolites Produced by Electrospray... The formation mechanisms of singly and multiply charged organophosphate metabolites by electrospray ionization (ESI) and their gas phase stabilities were investigated. Metabolites containing multiple phosphate groups, such as adenosine 5'-diphosphate (ADP), adenosine 5'-triphosphate (ATP), and D-myo-inositol-1,4,5-triphosphate (IP3) were observed as doubly deprotonated ions by negative-ion ESI mass spectrometry. Organophosphates with multiple negative charges were found to be unstable and often underwent loss of PO3 –, although singly deprotonated analytes were stable. The presence of fragments due to the loss of PO3 – in the negative-ion ESI mass spectra could result in the misinterpretation of analytical results. In contrast to ESI, matrix-assisted laser desorption ionization (MALDI) produced singly charged organophosphate metabolites with no associated fragmentation, since the singly charged anions are stable. The stability of an organophosphate metabolite in the gas phase strongly depends on its charge state. The fragmentations of multiply charged organophosphates were also investigated in detail through density functional theory calculations. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of The American Society for Mass Spectrometry Springer Journals

Gas-Phase Stability of Negatively Charged Organophosphate Metabolites Produced by Electrospray Ionization and Matrix-Assisted Laser Desorption/Ionization

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Publisher
Springer Journals
Copyright
Copyright © 2017 by American Society for Mass Spectrometry
Subject
Chemistry; Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics
ISSN
1044-0305
eISSN
1879-1123
D.O.I.
10.1007/s13361-017-1795-8
Publisher site
See Article on Publisher Site

Abstract

The formation mechanisms of singly and multiply charged organophosphate metabolites by electrospray ionization (ESI) and their gas phase stabilities were investigated. Metabolites containing multiple phosphate groups, such as adenosine 5'-diphosphate (ADP), adenosine 5'-triphosphate (ATP), and D-myo-inositol-1,4,5-triphosphate (IP3) were observed as doubly deprotonated ions by negative-ion ESI mass spectrometry. Organophosphates with multiple negative charges were found to be unstable and often underwent loss of PO3 –, although singly deprotonated analytes were stable. The presence of fragments due to the loss of PO3 – in the negative-ion ESI mass spectra could result in the misinterpretation of analytical results. In contrast to ESI, matrix-assisted laser desorption ionization (MALDI) produced singly charged organophosphate metabolites with no associated fragmentation, since the singly charged anions are stable. The stability of an organophosphate metabolite in the gas phase strongly depends on its charge state. The fragmentations of multiply charged organophosphates were also investigated in detail through density functional theory calculations.

Journal

Journal of The American Society for Mass SpectrometrySpringer Journals

Published: Sep 5, 2017

References

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