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Volume 12 (1994), Issue 2, Pages 69-83

Electrospray Tandem Mass Spectrometry of 3'-azido-2',3'dideoxythymidine and of a Novel Series of 3'-azido-2',3',4'-trideoxy-4'thio-5-halogenouridines and their Respective α-Anomers

Joseph Banoub,1 Emmanuel Gentil,1 Bougrine Tber,2 Nour-Eddine Fahmi,2 Gino Ronco,2 Pierre Villa,2 and Grahame Mackenzie3

1Northwest Atlantic Fisheries Center, Science Branch, Toxicology Section P.o. Box 5667, AIC 5XI, Canada, and Department of Biochemistry, Memorial University of Newfoundland, st. John's, Newfoundland, AlB 3X9, Canada
2Laboratoire de Chimie Organique et Cinetique,, UFR des Sciences, Universite de Picardie, 150 rue Saint-Leu, 80000 Amiens, France
3School of Chemistry, University of Hull, Cottingham, Road, HULL, HU6 7RX, UK

Copyright © 1994 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Electrospray mass spectrometry has aided the structural characterization of 3'-azido-2',3'-dideoxythymidine (AZI) and the novel series of 3'-azido-2',3',4'trideoxy-4'-thio-S-(bromo, chi oro or fluoro )uridine nucleosides and their respective α.anomers. Low energy CAD MS/MS analysis of the protonated molecules [M+H]+ confmned the predicted fragmentation route for AZT and a series of related 4'-thio-S-halogenouridines. This MSIMS study also provided characteristic fingerprint patterns which permitted differentiation of anomers within the series of 3'-azido-2' ,3' ,4' -trideoxy-4' -thio-S-halogenouridine nucleosides.