Fragmentation of aromatic sulfonamides in electrospray ionization mass spectrometry: Elimination of SO2 via rearrangement

Journal of Mass Spectrometry

Volumn 43, Issue 3, 2008, Pages 383-393

  Sun, Mingjiang ^a   Dai, Wenning ^a   Liu, David Q ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Arylsulfonamides; Loss of 64; Loss of SO2; SO2; SO2 extrusion; Tandem mass spectrometry

Indexed keywords

ATMOSPHERIC PRESSURE; BOND STRENGTH (CHEMICAL); ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; SULFUR DIOXIDE;

AROMATIC SULFONAMIDES; ATMOSPHERIC PRESSURE IONIZATION; FRAGMENTATION BEHAVIORS;

AMIDES;

SULFONAMIDE; SULFUR OXIDE;

ANALYTIC METHOD; ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL BOND; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; ELIMINATION REACTION; GAS; HYDROPHILICITY; MOLECULAR INTERACTION; PHARMACOPHORE; PREDICTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

BENZENE DERIVATIVES; GASES; IONS; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFONAMIDES; SULFUR DIOXIDE;

EID: 40649123020     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1335     Document Type: Article

References (20)

1. Sisodia CS, Stowe CM. Mechanism of excretion of sulfonamides in bovine milk. Indian Veterinary Journal 1964; 41: 711.
2. Pandya R, Murashima T, Tedeschi L, Barrett AGM. Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides. Journal of Organic Chemistry 2003; 68: 8274.
3. Ermer J. The use of hyphenated LC-MS technique for characterization of impurity profiles during drug development. Journal of Pharmaceutical and Biomedical Analysis 1998; 18: 707.
4. 2 from sulfonamides in collision-induced dissociation. Rapid Communications in Mass Spectrometry 2003; 17: 81.
5. Hellwinkel D, Lenz R. Possibilities and limits of the anionically induced sulfonamide-amino sulfone rearrangement. Chemische Berichte 1985; 118: 66.
6. Patino N, Di Giorgio C, Dan-Covalciuc C, Peytou V, Terreux R, Cabrol-Bass D, Bailly C, Condom R. Modeling, synthesis and biological evaluation of an ethidium-arginine conjugate linked to a ribonuclease mimic directed against TAR RNA of HIV-1. European Journal of Medical Chemistry 2002; 37: 573.
7. Ovcharenko V, Rzadkowska M, Tkaczynski T, Matosiuk D, Pihlaja K. Electron impact mass spectra of substituted 1-aryl-2-arylsulfonylamino-d2-imidzazolines. Rapid Communications in Mass Spectrometry 1997; 11: 1043.
8. Daly WH, Heurtevant CW. Mass spectrometry of O-alkyl-N-arylsulfonyl carbamates. Organic Mass Spectrometry 1970; 4: 165.
9. Braselton WE Jr, Bransome ED Jr, Ashline HC, Stewart JT, Honigberg IL. Gas chromatographic and mass spectral properties of sulfonylurea N-methyl-N′-perfluoroacyl derivatives. Analytical Chemistry 1976; 48: 1386.
10. Tang BS, Lu YQ. Electron impact and field desorption mass spectrometry of 2,4-diamino-6-substituted quinazoline sulfonamides. YaoXueXueBao 1984; 19: 415.
11. Lee J, Yoo HH, Kang MY, Kim DH. Low-energy collision-induced dissociation of sildenafil thiono analogues: gas-phase intramolecular nucleophilic substitution through ion-neutral complexes between a cationic substrate and a thione-containing neutral nucleophile. Rapid Communications in Mass Spectrometry 2005; 19: 1767.
12. Wang HY, Zhang X, Qian R, Guo YL, Lu L. Gas-phase sulfonyl-sulfinate rearrangement of protonated 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine. Rapid Communications in Mass Spectrometry 2006; 20: 2773.
13. van Rhijn JA, Lasaroms JJP, Berendsen BJA, Brinkman UAT. Liquid chromatographic-tandem mass spectrometric determination of selected sulphonamides in milk. Journal of Chromatography A 2002; 960: 121.
14. Verzegnassi L, Savoy-Perroud MC, Stadler RH. Application of liquid chromatography-electrospray ionization tandem mass spectrometry to the detection of 10 sulfonamides in honey. Journal of Chromatography A 2002; 977: 77.
15. Duffield AM, Djerassi C, Neidlein R, Heukelbach E. Mass spectrometry in structural and stereochemical problems. CLXXIV. Electron-impact induced fragmentation of some aryl-and alkylsulfonylthioureas. Organic Mass Spectrometry 1969; 2: 641.
16. Binkley RW, Flechtner TW, Tevesz MJS, Winnik W, Zhong B. Rearrangement of aromatic sulfonate anions in the gas phase. Organic Mass Spectrometry 1993; 28: 769.
17. Brown P, Djerassi C. Electron impact-induced rearrangement of organic molecules. Angewandte Chemie 1967; 79: 481.
18. Reddy PN, Srikanth R, Venkateswarlu N, Rao RNa, Srinivas R. Electrospray ionization tandem mass spectrometric study of three isomeric substituted aromatic sulfonic acids; differentiation via ortho effects. Rapid Communications in Mass Spectrometry 2005; 19: 72.
19. Grostic MF, Wnuk RJ, MacKellar FA. The mass spectrometry of sulfonylureas. I. Mechanisms for the loss of sulfur dioxide. Journal of the American Chemical Society 1966; 88: 4664.
20. Mueller P, Nguyen TMP. ipso-Substitution with the sodium salt of N-alkyl-p-nitrobenzenesulfonamide. A novel anionic rearrangement. Helvetica Chimica Acta 1979; 62: 494.