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

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.