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

Banoub, Joseph; Gentil, Emmanuel; Tber, Bougrine; Fahmi, Nour-Eddine; Ronco, Gino; Villa, Pierre; Mackenzie, Grahame

doi:https://doi.org/10.1155/1994/817395

Journal of Spectroscopy

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Volume 12 | Article ID 817395 | https://doi.org/10.1155/1994/817395

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

Abstract

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.

Copyright

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.

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