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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
Summary
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.
- 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.