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5′-Deoxy-5-Fluorouridine: Characterisation, Crystal Structure and Molecular Conformations Determined from X-Ray Powder Data

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Abstract

The title compound [systematic name: 1-[(1R,2R,3S,4R)-2,3-dihydroxy-4-methyltetrahydrofuranyl]-5-fluoropyrimidine-2,4(1H,3H)-dione], C9H11FN2O5, is a prodrug of 5-fluorouracil used as a cytostatic in cancer therapy. Its crystal structure was determined from laboratory X-ray powder diffraction data. The compound crystallises in the triclinic space group P1 with two molecules in the asymmetric unit. These symmetrically independent molecules differ in their hydrogen-bond patterns, the pseudorotational angles P of their furanosyl fragments as well as their N-glycosidic torsion angles χ.

Graphical Abstract

The crystal structure of 5′-deoxy-5-fluorouridine, 1-[(1R,2R,3S,4R)-2,3-dihydroxy-4-methyltetrahydrofuranyl]-5-fluoropyrimidine-2,4(1H,3H)-dione], C9H11FN2O5, a prodrug of 5-fluorouracil used as a cytostatic in cancer therapy, was determined from laboratory X-ray powder diffraction data. The compound crystallises in the triclinic space group P1 with two symmetrically independent molecules differing in their hydrogen-bond patterns, the pseudorotational angles P of their furanosyl fragments as well as their N-glycosidic torsion angles χ.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Inorganic and Analytical Chemistry, Goethe-University Frankfurt am Main, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany

    Sándor L. Bekö, David Urmann & Martin U. Schmidt

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  1. Sándor L. Bekö
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  2. David Urmann
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  3. Martin U. Schmidt
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Correspondence to Martin U. Schmidt.

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Bekö, S.L., Urmann, D. & Schmidt, M.U. 5′-Deoxy-5-Fluorouridine: Characterisation, Crystal Structure and Molecular Conformations Determined from X-Ray Powder Data. J Chem Crystallogr 42, 933–940 (2012). https://doi.org/10.1007/s10870-012-0339-0

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