Mass Spectrometric studies of anomeric glycopyranosyl azides

Zoltán Dinya, Péter Benke, Zoltán Györgydeák, László Somsák, József Jekö, István Pintér, János Kuszman, Jean Pierre Praly

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6 Citations (Scopus)

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 N3 radical or N2 molecule. Loss of N2 molecule and the protonation of the derived nitrene were characteristic of the studied compounds. The presence of BF3 · Et2O 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 - N2]+ ion makes it possible to identify the anomeric configuration of the azido group.

Original languageEnglish
Pages (from-to)211-219
Number of pages9
JournalJournal of Mass Spectrometry
Volume36
Issue number2
DOIs
Publication statusPublished - Mar 14 2001

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Keywords

  • Anomeric effect
  • Glycopyranosyl azide
  • Mass spectrometry
  • Nitrene
  • Structure elucidation

ASJC Scopus subject areas

  • Spectroscopy

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