Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry

Sheng, Huaming; Tang, Weijuan; Yerabolu, Ravikiran; Kong, John Y.; Williams, Peggy E.; Zhang, Minli; Kenttämaa, Hilkka I.

doi:10.1002/rcm.7154

Title: Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry

Abstract

Rationale N ‐Monosubstituted hydroxylamines correspond to an important class of metabolites for many bioactive molecules. In this study, a tandem mass spectrometric method based on ion/molecule reactions was developed for the identification of compounds with the N ‐monosubstituted hydroxylamino functionality. Methods The diagnostic ion/molecule reaction occurs between protonated analytes with 2‐methoxypropene (MOP) inside a linear quadrupole ion trap mass spectrometer. Results Most protonated compounds with N ‐monosubstituted and disubstituted hydroxylamino and oxime functional groups react with MOP via proton transfer and formation of a stable adduct in a linear quadrupole ion trap mass spectrometer. However, only protonated compounds with N ‐monosubstituted hydroxylamino groups form the characteristic MOP adduct–MeOH product. Possible mechanisms of this reaction are discussed. Conclusions A method based on functional group‐selective ion/molecule reactions in a linear quadrupole ion trap mass spectrometer has been demonstrated to allow the identification of protonated compounds with the N ‐monosubstituted hydroxylamino functionality. Only N ‐monosubstituted hydroxylamines react with MOP via formation of an adduct that has eliminated methanol. Copyright © 2015 John Wiley & Sons, Ltd.

Authors:

Sheng, Huaming ^[1]; Tang, Weijuan ^[1]; Yerabolu, Ravikiran ^[1]; Kong, John Y. ^[1]; Williams, Peggy E. ^[1]; Zhang, Minli ^[2]; Kenttämaa, Hilkka I. ^[1]

Purdue University Department of Chemistry West Lafayette IN 47907 USA
AstraZeneca Boston MA 02130 USA

Publication Date:: Mon Mar 16 00:00:00 EDT 2015

Sponsoring Org.:: USDOE

OSTI Identifier:: 1400695

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Rapid Communications in Mass Spectrometry

Additional Journal Information:: Journal Name: Rapid Communications in Mass Spectrometry Journal Volume: 29 Journal Issue: 8; Journal ID: ISSN 0951-4198

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Sheng, Huaming, Tang, Weijuan, Yerabolu, Ravikiran, Kong, John Y., Williams, Peggy E., Zhang, Minli, and Kenttämaa, Hilkka I. Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry.  United Kingdom: N. p., 2015. 
Web.  doi:10.1002/rcm.7154.

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                    Sheng, Huaming, Tang, Weijuan, Yerabolu, Ravikiran, Kong, John Y., Williams, Peggy E., Zhang, Minli, & Kenttämaa, Hilkka I. Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry.  United Kingdom.  https://doi.org/10.1002/rcm.7154

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                    Sheng, Huaming, Tang, Weijuan, Yerabolu, Ravikiran, Kong, John Y., Williams, Peggy E., Zhang, Minli, and Kenttämaa, Hilkka I. Mon .  
"Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry".  United Kingdom.  https://doi.org/10.1002/rcm.7154.

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@article{osti_1400695,

  title        = {Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry},

  author       = {Sheng, Huaming and Tang, Weijuan and Yerabolu, Ravikiran and Kong, John Y. and Williams, Peggy E. and Zhang, Minli and Kenttämaa, Hilkka I.},

  abstractNote = {Rationale N ‐Monosubstituted hydroxylamines correspond to an important class of metabolites for many bioactive molecules. In this study, a tandem mass spectrometric method based on ion/molecule reactions was developed for the identification of compounds with the N ‐monosubstituted hydroxylamino functionality. Methods The diagnostic ion/molecule reaction occurs between protonated analytes with 2‐methoxypropene (MOP) inside a linear quadrupole ion trap mass spectrometer. Results Most protonated compounds with N ‐monosubstituted and disubstituted hydroxylamino and oxime functional groups react with MOP via proton transfer and formation of a stable adduct in a linear quadrupole ion trap mass spectrometer. However, only protonated compounds with N ‐monosubstituted hydroxylamino groups form the characteristic MOP adduct–MeOH product. Possible mechanisms of this reaction are discussed. Conclusions A method based on functional group‐selective ion/molecule reactions in a linear quadrupole ion trap mass spectrometer has been demonstrated to allow the identification of protonated compounds with the N ‐monosubstituted hydroxylamino functionality. Only N ‐monosubstituted hydroxylamines react with MOP via formation of an adduct that has eliminated methanol. Copyright © 2015 John Wiley & Sons, Ltd.},

  doi          = {10.1002/rcm.7154},

  journal      = {Rapid Communications in Mass Spectrometry},

  number       = 8,

  volume       = 29,

  place        = {United Kingdom},

  year         = {Mon Mar 16 00:00:00 EDT 2015},

  month        = {Mon Mar 16 00:00:00 EDT 2015}

}

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Works referenced in this record:

2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT
journal, March 2004

Helsby, N. A.; Ferry, D. M.; Patterson, A. V.
British Journal of Cancer, Vol. 90, Issue 5
DOI: 10.1038/sj.bjc.6601612

Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers
journal, October 2011

Eismin, Ryan J.; Fu, Mingkun; Yem, Sonoeun
Journal of The American Society for Mass Spectrometry, Vol. 23, Issue 1
DOI: 10.1007/s13361-011-0249-y

Estimation of effective ion temperatures in a quadrupole ion trap
journal, August 1998

Gronert, Scott
Journal of the American Society for Mass Spectrometry, Vol. 9, Issue 8
DOI: 10.1016/S1044-0305(98)00055-5

Parametrization of the ion–polar molecule collision rate constant by trajectory calculations
journal, May 1982

Su, Timothy; Chesnavich, Walter J.
The Journal of Chemical Physics, Vol. 76, Issue 10
DOI: 10.1063/1.442828

Identification of a Hydroxylamine Glucuronide Metabolite of an oral Hypoglycemic Agent
journal, January 2004

Miller, Randall R.; Doss, George A.; Stearns, Ralph A.
Drug Metabolism and Disposition, Vol. 32, Issue 2
DOI: 10.1124/dmd.32.2.178

Liquid Chromatography–Electrospray Ionization Tandem Mass Spectrometric Analysis of 2-Alkylcyclobutanones in Irradiated Chicken by Precolumn Derivatization with Hydroxylamine
journal, June 2013

Ye, Yuran; Liu, Hanxia; Horvatovich, Peter
Journal of Agricultural and Food Chemistry, Vol. 61, Issue 24
DOI: 10.1021/jf401446n

Functional Group Selective Ion/Molecule Reactions: Mass Spectrometric Identification of the Amido Functionality in Protonated Monofunctional Compounds
journal, April 2007

Campbell, Karinna M.; Watkins, Michael A.; Li, Sen
The Journal of Organic Chemistry, Vol. 72, Issue 9
DOI: 10.1021/jo0618223

Ion–molecule reactions facilitate the identification and differentiation of primary, secondary and tertiary amino functionalities in protonated monofunctional analytes in mass spectrometry
journal, May 2009

Fu, Mingkun; Eismin, Ryan J.; Duan, Penggao
International Journal of Mass Spectrometry, Vol. 282, Issue 3
DOI: 10.1016/j.ijms.2009.01.018

Quadrupole ion trap studies of fundamental organic reactions
journal, January 2004

Gronert, Scott
Mass Spectrometry Reviews, Vol. 24, Issue 1
DOI: 10.1002/mas.20008

A two-dimensional quadrupole ion trap mass spectrometer
journal, June 2002

Schwartz, Jae C.; Senko, Michael W.; Syka, John E. P.
Journal of the American Society for Mass Spectrometry, Vol. 13, Issue 6
DOI: 10.1016/S1044-0305(02)00384-7

Ion–Molecule Reactions: Analytical and Structural Tool
journal, November 2012

Osburn, Sandra; Ryzhov, Victor
Analytical Chemistry, Vol. 85, Issue 2
DOI: 10.1021/ac302920a

Identification of Aliphatic and Aromatic Tertiary N-Oxide Functionalities in Protonated Analytes via Ion/Molecule and Dissociation Reactions in an FT-ICR Mass Spectrometer
journal, February 2009

Duan, Penggao; Fu, Mingkun; Gillespie, Todd A.
The Journal of Organic Chemistry, Vol. 74, Issue 3
DOI: 10.1021/jo802001e

Identification of the Sulfone Functionality in Protonated Analytes via Ion/Molecule Reactions in a Linear Quadrupole Ion Trap Mass Spectrometer
journal, March 2014

Sheng, Huaming; Williams, Peggy E.; Tang, Weijuan
The Journal of Organic Chemistry, Vol. 79, Issue 7
DOI: 10.1021/jo402645a

Quantification of 3-Nitrobenzanthrone-DNA Adducts Using Online Column-Switching HPLC-Electrospray Tandem Mass Spectrometry
journal, November 2009

Gamboa da Costa, Gonçalo; Singh, Rajinder; Arlt, Volker M.
Chemical Research in Toxicology, Vol. 22, Issue 11
DOI: 10.1021/tx900264v

Differentiation of Protonated Aromatic Regioisomers Related to Lignin by Reactions with Trimethylborate in a Fourier Transform Ion Cyclotron Resonance Mass Spectrometer
journal, April 2011

Somuramasami, Jayalakshmi; Duan, Penggao; Amundson, Lucas M.
Journal of The American Society for Mass Spectrometry, Vol. 22, Issue 6
DOI: 10.1007/s13361-011-0099-7

Dapsone toxicity: Some current perspectives
journal, November 1995

Coleman, Michael D.
General Pharmacology: The Vascular System, Vol. 26, Issue 7
DOI: 10.1016/0306-3623(95)00029-1

Electrospray Ionization Mass Spectrometric Study of N-Oxidation Products of Clenbuterol
journal, June 1997

Debrauwer, L.; Zalko, D.; Bories, G.
Rapid Communications in Mass Spectrometry, Vol. 11, Issue 10
DOI: 10.1002/(SICI)1097-0231(19970630)11:10<1089::AID-RCM978>3.0.CO;2-R

Gas chromatographic–mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes
journal, March 1999

Peng, Sean X.; Strojnowski, Michael J.; Hu, Joanna K.
Journal of Chromatography B: Biomedical Sciences and Applications, Vol. 724, Issue 1
DOI: 10.1016/S0378-4347(98)00557-X

Gas-Phase Reactivity of Hydroxylamine toward Charged Electrophiles. A Mass Spectrometric and Computational Study of the Protonation and Methylation of H2NOH
journal, April 1995

Angelelli, F.; Aschi, M.; Cacace, F.
The Journal of Physical Chemistry, Vol. 99, Issue 17
DOI: 10.1021/j100017a041

Identification of the sulfoxide functionality in protonated analytes via ion/molecule reactions in linear quadrupole ion trap mass spectrometry
journal, January 2014

Sheng, Huaming; Williams, Peggy E.; Tang, Weijuan
The Analyst, Vol. 139, Issue 17
DOI: 10.1039/C4AN00677A

Identification of the Carboxylic Acid Functionality by Using Electrospray Ionization and Ion−Molecule Reactions in a Modified Linear Quadrupole Ion Trap Mass Spectrometer
journal, May 2008

Habicht, Steven C.; Vinueza, Nelson R.; Archibold, Enada F.
Analytical Chemistry, Vol. 80, Issue 9
DOI: 10.1021/ac800002h

Regioselective ion–molecule reactions for the mass spectrometric differentiation of protonated isomeric aromatic diamines
journal, January 2008

Fu, Mingkun; Duan, Penggao; Li, Sen
The Analyst, Vol. 133, Issue 4
DOI: 10.1039/b801961d

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Title: Mass spectrometric identification of the N ‐monosubstituted N ‐hydroxylamino functionality in protonated analytes via ion/molecule reactions in tandem mass spectrometry

Abstract

Citation Formats

2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT journal, March 2004

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Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers
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Estimation of effective ion temperatures in a quadrupole ion trap
journal, August 1998

Parametrization of the ion–polar molecule collision rate constant by trajectory calculations
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Liquid Chromatography–Electrospray Ionization Tandem Mass Spectrometric Analysis of 2-Alkylcyclobutanones in Irradiated Chicken by Precolumn Derivatization with Hydroxylamine
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Functional Group Selective Ion/Molecule Reactions: Mass Spectrometric Identification of the Amido Functionality in Protonated Monofunctional Compounds
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