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Nucleic Acids Research, 1981, Vol. 9, No. 3 711-729
© 1981

CHEMISTRY

The crystal and molecular structure of 2':-deoxy-2':-fluoroinosine monohydrate

Toshio Hakoshima, Hisako Omori, Ken-ichi Tomita, Hiroko Miki and Morio Ikehara

Faculty of Pharmaceutical Sciences, Osaka University 133-1 Yamada-kami, Suita, Osaka 565, Japan

Received November 17, 1980. The structure of the hydrate of 2'-deoxy-2'-fluoroinosine has been determined by single-crystal x-ray diffraction. The nucleoslde crystallises inspace group P212121, with unit cell dimensions, a = 33.291, b = 10. 871, c = 6.897Å. There are two nucleosides and two water molecules in the asymmetric unit. The structure was solved by direct methods and refined to a residual R = 0.095. The two independent nucleosides in the asymmetric unit show different conformations about the glycosidic bond, while other structural detailsare similar. The base orientation to the sugar is syn in molecule A, whereas anti in molecule B. The exocyclic C(4')–C(5') bond conformation defined withrespect to C(3')–C(4')–C(5')–C(5') is gauche+ in both molecules A and B. The sugar ring pucker defined by the pseudorotation phase angle P is a twisted conformation in both, C(3')-endo-C(4')-exo with P = 29° in molecule A and C(4')-exo-C(3')-endo with P = 41° in molecule B. It is shown by comparison with x-ray results of other 2'-fluoro nucleosides and un modified nucleosides including inosines that, in addition to a strong preference of the C(3')-endotype pucker, twisted conformations involving C(4')-exo puckering may be one of characteristic features of 2'-fluoronucleosides.


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