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. 1964 May;4(3):203–225. doi: 10.1016/s0006-3495(64)86778-3

The Crystal and Molecular Structure of 5-Fluoro-2′-Deoxy-β-Uridine

David R Harris, Walter M Macintyre
PMCID: PMC1367500  PMID: 14185582

Abstract

The crystal structure of 5-fluoro-2′-deoxy-β-uridine (FUDR) has been solved and the details of the molecular structure determined by x-ray analysis. The bond lengths and angles have been measured and are compared with the dimensions found for calcium thymidylate and adenylic acid. In all three compounds the bonds formed by the nitrogen atom involved in the glycosidic bond are not coplanar. Furthermore, it is found that in FUDR the C2′ carbon atom is out of the plane of the ribose ring. The possible effect of these observations on nucleic acid structures is discussed.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BROCKMAN R. W., BENNETT L. L., Jr, SIMPSON M. S., WILSON A. R., THOMSON J. R., SKIPPER H. E. A mechanism of resistance to 8-azaguanine. II. Studies with experimental neoplasms. Cancer Res. 1959 Sep;19:856–869. [PubMed] [Google Scholar]
  2. CHAUDHURI N. K., MONTAG B. J., HEIDELBERGER C. Studies on fluorinated pyrimidines. III. The metabolism of 5-fluorouracil-2-C14 and 5-fluoroorotic-2-C14 acid in vivo. Cancer Res. 1958 Apr;18(3):318–328. [PubMed] [Google Scholar]
  3. DONOHUE J., TRUEBLOOD K. N. Base pairing in DNA. J Mol Biol. 1960 Dec;2:363–371. doi: 10.1016/s0022-2836(60)80047-2. [DOI] [PubMed] [Google Scholar]
  4. EIDINOFF M. L., RICH M. A. Growth inhibition of a human tumor cell strain by 5-fluoro-2-deoxyuridine: time parameters for subsequent reversal by thymidine. Cancer Res. 1959 Jun;19(5):521–524. [PubMed] [Google Scholar]
  5. PRUSOFF W. H. Studies on the mechanism of action of 5-iododeoxyuridine, an analog of thymidine. Cancer Res. 1960 Jan;20:92–95. [PubMed] [Google Scholar]
  6. SPENCER M., FULLER W., WILKINS M. H., BROWN G. L. Determination of the helical configuration of ribonucleic acid molecules by X-ray diffraction study of crystalline amino-acid-transfer ribonucleic acid. Nature. 1962 Jun 16;194:1014–1020. doi: 10.1038/1941014a0. [DOI] [PubMed] [Google Scholar]
  7. WELCH A. D. Some metabolic approaches to cancer chemotherapy. Cancer Res. 1961 Dec;21:1475–1490. [PubMed] [Google Scholar]

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