Mass spectrometric studies of anomeric glycopyranosyl azides

Citation
Z. Dinya et al., Mass spectrometric studies of anomeric glycopyranosyl azides, J MASS SPEC, 36(2), 2001, pp. 211-219
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Spectroscopy /Instrumentation/Analytical Sciences
Journal title
JOURNAL OF MASS SPECTROMETRY
ISSN journal
10765174 → ACNP
Volume
36
Issue
2
Year of publication
2001
Pages
211 - 219
Database
ISI
SICI code
1076-5174(200102)36:2<211:MSSOAG>2.0.ZU;2-X
Abstract
We studied the mass spectrometric behaviour of peracetylated and underivati zed anomeric hexopyranosyl azides and 5-thioglucopyranosyl azides by means of different mass spectrometric techniques. The unstable molecular ions fra gment predominantly by losing either N-3 radical or N-2 molecule. Loss of N -2 molecule and the protonation of the derived nitrene were characteristic of the studied compounds. The presence of BF3 . Et2O in the ion source is f avorable for producing; the protonated nitrene form. The protonated nitrene shows a new type of ring expansion rearrangement. The abundances of the [M + H - N-2](+) ion makes it possible to identify the anomeric configuration of the azido group. Copyright (C) 2001 John Wiley & Sons, Ltd.