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5-Methyl-2'-deoxy-4'-thio-alpha-uridine (R)-S-oxide.

M Sun1, A C Macculloch, T A Hamor

  • 1School of Chemistry, University of Birmingham, Birmingham B15 2TT, England.

Acta Crystallographica. Section C, Crystal Structure Communications
|December 19, 2000
PubMed
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This study details the molecular structure of a novel compound, revealing a planar pyrimidine ring and a C3'-endo thiosugar conformation. These findings are crucial for understanding nucleoside analog interactions and potential therapeutic applications.

Area of Science:

  • Crystallography and Molecular Modeling
  • Organic Chemistry
  • Biochemistry

Background:

  • Nucleoside analogs are vital in antiviral and anticancer therapies.
  • Understanding the precise three-dimensional structure of modified nucleosides is essential for drug design.
  • Thiosugar modifications can alter nucleoside properties and biological activity.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(10)H(14)N(2)O(5)S.
  • To determine the spatial arrangement and conformation of the pyrimidine and thiosugar rings.
  • To provide detailed structural data for nucleoside analog research.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Analysis of bond lengths, bond angles, and torsion angles.

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  • Comparison with standard nucleoside conformations.

    • Main Results:

    • The pyrimidine ring is planar (deviation within 0.024 Å).
    • The pyrimidine ring is oriented at 75.46° relative to the thiosugar ring plane.
    • The thiosugar ring adopts a C3 -endo conformation with a syn glycosidic torsion angle (S4 -C1 -N1-C2 = -52.1°).

    Conclusions:

    • The determined structure provides a precise geometric description of this modified nucleoside.
    • The syn glycosidic conformation and C3 -endo sugar pucker are key features influencing molecular interactions.
    • This structural data can inform the design of new nucleoside-based therapeutics.