title: Gas-phase ion-molecule reactions for the identification of the sulfone functionality in protonated analytes in a linear quadrupole ion trap mass spectrometer.
abstract: 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.
  
  
  
  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.
  
  
  
  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.
  
  
  
  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.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.|DuPont, 200 Powder Mill Rd., Wilmington, DE, 19843, USA.
authors.forename: Weijuan
authors.initials: W
authors.lastname: Tang
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.|Merck, 125 E Lincoln Ave, Rahway, NJ, 07065, USA.
authors.forename: Huaming
authors.initials: H
authors.lastname: Sheng
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.
authors.forename: John Y
authors.initials: JY
authors.lastname: Kong
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.
authors.forename: Ravikiran
authors.initials: R
authors.lastname: Yerabolu
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.
authors.forename: Hanyu
authors.initials: H
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.
authors.forename: Joann
authors.initials: J
authors.lastname: Max
authors.affiliation: AstraZeneca, Waltham, MA, 02541, USA.
authors.forename: Minli
authors.initials: M
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA.
authors.forename: Hilkka I
authors.initials: HI
authors.lastname: Kenttämaa
mesh_terms: D009930:Organic Chemicals; D011522:Protons; D013450:Sulfones / Q000737:chemistry*; D013454:Sulfoxides; D053719:Tandem Mass Spectrometry
chemical_list: D009930:Organic Chemicals; D011522:Protons; D013450:Sulfones; D013454:Sulfoxides