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Gas‐phase ion–molecule reactions for the identification of the sulfone functionality in protonated analytes in a linear quadrupole ion trap mass spectrometer
Author(s) -
Tang Weijuan,
Sheng Huaming,
Kong John Y.,
Yerabolu Ravikiran,
Zhu Hanyu,
Max Joann,
Zhang Minli,
Kenttämaa Hilkka I.
Publication year - 2016
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.7569
Subject(s) - chemistry , sulfone , quadrupole ion trap , protonation , ion trap , adduct , sulfoxide , mass spectrometry , reagent , triple quadrupole mass spectrometer , photochemistry , tandem mass spectrometry , selected reaction monitoring , organic chemistry , ion , chromatography
Rationale The oxidation of sulfur atoms is an important biotransformation pathway for many sulfur‐containing drugs. In order to rapidly identify the sulfone functionality in drug metabolites, a tandem mass spectrometric method based on ion–molecule reactions was developed. Methods A phosphorus‐containing reagent, trimethyl phosphite (TMP), was allowed to react with protonated analytes with various functionalities in a linear quadrupole ion trap mass spectrometer. The reaction products and reaction efficiencies were measured. Results Only protonated sulfone model compounds were found to react with TMP to form a characteristic [TMP adduct–MeOH] product ion. All other protonated compounds investigated, with functionalities such as sulfoxide, N‐oxide, hydroxylamino, keto, carboxylic acid, and aliphatic and aromatic amino, only react with TMP via proton transfer and/or addition. The specificity of the reaction was further demonstrated by using a sulfoxide‐containing anti‐inflammatory drug, sulindac, as well as its metabolite sulindac sulfone. Conclusions A method based on functional group‐selective ion–molecule reactions in a linear quadrupole ion trap mass spectrometer has been demonstrated for the identification of the sulfone functionality in protonated analytes. A characteristic [TMP adduct–MeOH] product ion was only formed for the protonated sulfone analytes. The applicability of the TMP reagent in identifying sulfone functionalities in drug metabolites was also demonstrated. Copyright © 2016 John Wiley & Sons, Ltd.