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Mass spectrometric studies of anomeric glycopyranosyl azides
Author(s) -
Dinya Zoltán,
Benke Péter,
Györgydeák Zoltán,
Somsák László,
Jekö József,
Pintér István,
Kuszman János,
Praly JeanPierre
Publication year - 2001
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.112
Subject(s) - chemistry , protonation , nitrene , anomer , molecule , ion , ring (chemistry) , computational chemistry , stereochemistry , organic chemistry , catalysis
Abstract We studied the mass spectrometric behaviour of peracetylated and underivatized anomeric hexopyranosyl azides and 5‐thioglucopyranosyl azides by means of different mass spectrometric techniques. The unstable molecular ions fragment 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 BF 3 ·Et 2 O in the ion source is favorable 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 © 2001 John Wiley & Sons, Ltd.