Electrospray tandem mass-spectrometric analysis of diastereo- and stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[ c]furan core

Electrospray mass spectrometry and tandem mass spectrometry have aided the structural characterization of the diastereoisomeric cis- and trans-1-(3-benzoyloxymethyl-1,3-dihydrobenzo[ c]furan-1-yl)thymines and the four enantiomerically pure stereoisomers of uracil analogues. Low-energy collision-indu...

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Bibliographic Details
Published in:Carbohydrate research 2003-10, Vol.338 (22), p.2311-2324
Main Authors: Len, Christophe, Mackenzie, Grahame, Ewing, David F., Sheppard, George, Banoub, Joseph
Format: Article
Language:English
Subjects:
Animals
Benzofurans - chemistry
Electrospray tandem mass spectrometry
Molecular Structure
Pyrimidine Nucleosides - chemistry
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
Structural characterization
Thymine - analogs & derivatives
Thymine - chemistry
Thymine diastereoisomers
Uracil enantiomers of 1,3-dihydrobenzo[ c]furan nucleosides
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Summary:Electrospray mass spectrometry and tandem mass spectrometry have aided the structural characterization of the diastereoisomeric cis- and trans-1-(3-benzoyloxymethyl-1,3-dihydrobenzo[ c]furan-1-yl)thymines and the four enantiomerically pure stereoisomers of uracil analogues. Low-energy collision-induced dissociation MS/MS analysis of the various precursor molecular and cluster ions confirmed the characteristic fingerprint pattern obtained in the conventional electrospray spectra and allowed a convenient method for the characterization of novel 1,3-dihydrobenzo[ c]furan nucleosides. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2003.08.017