Premium
The unanticipated loss of SO 2 from sulfonamides in collision‐induced dissociation
Author(s) -
Wang Zhen,
Hop Cornelis E. C. A.,
Kim MiSook,
Huskey SuE. W.,
Baillie Thomas A.,
Guan Ziqiang
Publication year - 2002
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.877
Subject(s) - chemistry , fourier transform ion cyclotron resonance , mass spectrometry , tandem mass spectrometry , fragmentation (computing) , collision induced dissociation , moiety , dissociation (chemistry) , sulfonamide , ion , ion cyclotron resonance , top down proteomics , molecule , medicinal chemistry , chromatography , stereochemistry , selected reaction monitoring , organic chemistry , cyclotron , computer science , operating system
A potent and selective sulfonamide β3 agonist with an excellent pharmacokinetic profile has recently been synthesized. During the analysis by liquid chromatography/tandem mass spectrometry (LC/MS/MS) of metabolites of the sulfonamide N ‐{4‐[2‐(2‐hydroxy‐2‐pyridin‐3‐ylethylamino)ethyl]phenyl}‐4‐[4‐(4‐trifluoromethylphenyl)thiazol‐2‐yl]benzulfonamide (compound A), we observed loss of 64 Da for a few of the metabolites in the negative ion mode. Accurate mass measurements performed with Fourier transform ion cyclotron resonance (FTICR) mass spectrometry and quadrupole time‐of‐flight (Q‐TOF) mass spectrometry suggested that the loss of 64 Da corresponded to the loss of SO 2 . The same phenomenon was observed for a group of structurally related and commercially available compounds that also contain a sulfonamide moiety. MS/MS analysis of the fragment ions that had lost SO 2 in the ion source suggested that these ions were covalently bound rather than ion‐molecule complexes. The neutral loss involving the cleavage of two bonds was unanticipated and suggested a complex rearrangement process. A mechanism for the loss of SO 2 has been proposed. Copyright © 2002 John Wiley & Sons, Ltd.