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Related Experiment Videos

2'-Deoxy-5-methylisocytidine.

F Seela1, Y He, H Reuter

  • 1Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, D-49069 Osnabrück, Germany. fraseela@rz.uni-osnabrueck.de

Acta Crystallographica. Section C, Crystal Structure Communications
|August 16, 2000
PubMed
Summary
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This study details the molecular structure of 2-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidin-4(1H)-one, revealing a syn N-glycosidic bond and an unusual (O)T(1) sugar pucker in the deoxyribofuranose. The C4’-C5’ bond orientation is +sc (gauche).

Area of Science:

  • Structural chemistry
  • Nucleoside analogs
  • Organic chemistry

Background:

  • Understanding nucleoside structure is crucial for medicinal chemistry.
  • The conformation of nucleosides influences their biological activity.
  • 2-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidin-4(1H)-one is a pyrimidine nucleoside analog.

Purpose of the Study:

  • To elucidate the detailed three-dimensional structure of the title compound.
  • To characterize the conformation of the N-glycosidic bond and the sugar pucker.
  • To investigate the orientation of the exocyclic C4'-C5' bond.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed.
  • Conformational analysis of the nucleoside structure was performed.

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  • Spectroscopic methods may have been used for characterization (inferred).

    • Main Results:

    • The compound crystallizes with the chemical formula C(10)H(15)N(3)O(4).
    • The N-glycosidic bond adopts a syn conformation.
    • The 2-deoxyribofuranose moiety exhibits an unusual (O)T(1) sugar pucker.
    • The C4'-C5' bond is in the +sc (gauche) orientation.

    Conclusions:

    • The determined structure provides insights into the conformational preferences of pyrimidine nucleosides.
    • The unusual sugar pucker may have implications for molecular interactions and biological function.
    • This structural data serves as a reference for related nucleoside analog studies.