Electron ionization mass spectra of novel 2,3:4,5‐bis‐O‐(1‐methylethylidene)‐β‐D‐fructopyranose derivatives and related sugar sulfamates

Abstract

The electron-impact (EI) mass spectral fragmentation of ten bis-O-(l-methylethy1idene)fructopyranose derivatives and three related sugar sulfamates were investigated. and OH. The fragmentation of isomeric bis-O-(l-methylethylidene) derivatives of aldopyranose, ketopyranose and ketofuranose sulfamates was also investigated. The results indicate that isomeric sugar sulfamates can be easily distinguished in the EI mode. Key fragmentation pathways are discussed for these compounds.

Metabolism and excretion of the antiepileptic/antimigraine drug, topiramate in animals and humans

“…The MS (NH 3-CI) analysis of unchanged TPM revealed a significant protonated ammonium cation [M+ NH 4 "lat mlz 357. Based on previous electron ionization MS studies of TPM [16], a fragmentation scheme illustrating these neutral loss products is shown in Figure 2. The MS (NH 3-CI) spectra contained many characteristic fragment cations based on neutral loss of acetone from the dioxolane rings (m/z 299, and 241), neutral loss of HOS0 2NH2 (m/z 243) and a combination of both (m/z 185, 127, 113).…”

Characterization of stereoisomeric furanosidic derivatives by direct chemical ionization mass spectrometry and liquid secondary ion mass spectrometry with tandem mass spectrometry. (Part II)

“…As observed for other carbohydrate derivatives containing the 1,2-0-isopropylidene group, [14][15][16][17] fragmentation in this unit results in the elimination of acetone leading to the base peak at m/z 253, which appears to be most prevalent for compound 1.…”

Sulfamic Acid and Its N- and O-Substituted Derivatives

“…Further work using IR, Raman, and 13 C NMR on the 2:1 bis(betaine) sulfamate (see section ) has been reported . An EI/MS study of seven bis- O -(1-methylethylene)fructopyranose sulfamates including the well-known anticonvulsant topiramate 10 have revealed the fragmentation patterns, and the mechanisms involved are discussed …”

“…55 An EI/MS study of seven bis-O-(1-methylethylene)fructopyranose sulfamates including the well-known anticonvulsant topiramate 10 have revealed the fragmentation patterns, and the mechanisms involved are discussed. 56…”