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Electron ionization mass spectra of novel 2,3:4,5‐bis‐ O ‐(1‐methylethylidene)‐β‐ D ‐fructopyranose derivatives and related sugar sulfamates
Author(s) -
Caldwell Gary W.,
Sorgi Kirk L.,
Scott Lorraine,
Maryanoff Bruce E.,
Maryanoff Cynthia A.,
Masucci John A.,
Nortey Samuel O.,
Sisco William R.,
Micheel Arthur,
Ko ChanYan
Publication year - 1989
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210241204
Subject(s) - chemistry , fragmentation (computing) , electron ionization , sugar , mass spectrum , stereochemistry , molecule , medicinal chemistry , ionization , mass spectrometry , organic chemistry , ion , chromatography , computer science , operating system
The electron‐impact (EI) mass spectral fragmentation of ten bis‐ O ‐ (1‐methylethylidene)fructopyranose derivatives and three related sugar sulfamates were investigated. In particular, 2,3:4,5‐bis‐ O ‐ (1‐methylethylidene)‐β‐D‐fructopyranose sulfamate (topiramate), a potent anticonvulsant, was examined in greater detail. The fragmentation of the 2,3:4,5‐bis‐ O ‐(1‐methylethylidene) fructopyranose derivatives in general was not very dependent on the nature of substitution; the mechanisms of the common and unique fragmentation patterns are presented. These compounds showed characteristic peaks at m / z [M – 15] + , [M – 15 – 58] + , [M – 15 – 58 – 60] + , [M CH 2 X] + and [M CH 2 X – 58] + where X = OSO 2 NR 2 (R H, CH 3 , and/or Ph), OC (O)NHR, NH 2 , CI and OH. The fragmentation of isomeric bis‐ O ‐(1‐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.