A novel method for deuteration of 2′-deoxy-4′-thionucleosides

Oxidation of 2′-deoxy-5-ethyl-4′-thiouridine with sodium meta-periodate yielded a separable mixture of ( R) and( S)-sulfoxides. The structure of the ( R)-sulfoxide was confirmed by X-ray analysis. When treated with sodium deuteroxide, the H-4′ proton was exchanged for deuterium with epimerisation at...

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Bibliographic Details
Published in:Tetrahedron 1998-10, Vol.54 (41), p.12457-12464
Main Authors: MacCulloch, Alasdair C., Walker, Richard T.
Format: Article
Language:English
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Summary:Oxidation of 2′-deoxy-5-ethyl-4′-thiouridine with sodium meta-periodate yielded a separable mixture of ( R) and( S)-sulfoxides. The structure of the ( R)-sulfoxide was confirmed by X-ray analysis. When treated with sodium deuteroxide, the H-4′ proton was exchanged for deuterium with epimerisation at C-4′. Treatment of the deuteriated sulfoxide nucleoside with TFA/TMSBr furnished the starting material with H-4′ replaced by deuterium. A novel method for deuteration of 2′-deoxy-4′-thionucleosides by an oxidative/reductive process is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00727-3