NEGATIVE-ION MASS-SPECTROMETRY OF CARBOHYDRATES - A MECHANISTIC STUDYOF THE FRAGMENTATION REACTIONS OF DIDEOXY SUGARS

Authors
BINKLEY RW BINKLEY ER DUAN SM TEVESZ MJS WINNIK W
Citation
Rw. Binkley et al., NEGATIVE-ION MASS-SPECTROMETRY OF CARBOHYDRATES - A MECHANISTIC STUDYOF THE FRAGMENTATION REACTIONS OF DIDEOXY SUGARS, Journal of carbohydrate chemistry, 15(7), 1996, pp. 879-895
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
15
Issue
7
Year of publication
1996
Pages
879 - 895
Database
ISI
SICI code
0732-8303(1996)15:7<879:NMOC-A>2.0.ZU;2-F
Abstract
Hydroxyl group deprotonation of the alpha and beta anomers of methyl 3 -O-benzyl-2,6-dideoxy-D-arabino-hexopyranoside (1 and 2) occurs readil y in the gas phase to produce the corresponding anions 3 and 4, respec tively. Collisionally activated dissociation (CAD) of these anions cau ses fragmentation reactions that include ring opening, E2 elimination, and decarbonylation. Mechanisms for these reactions are proposed, and these mechanisms are supported by study of partially deuterated analo gs of 1 and 2.