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Related Experiment Videos

2'-Deoxy-5-fluorotubercidin.

Frank Seela1, Kuiying Xu, Henning Eickmeier

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

Acta Crystallographica. Section C, Crystal Structure Communications
|June 3, 2005
PubMed
Summary

This study details the molecular structure of 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. Key findings include its glycosyl bond conformation and a complex three-dimensional hydrogen-bond network.

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Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Structural Biology

Background:

  • Pyrrolo[2,3-d]pyrimidines are a significant class of heterocyclic compounds with diverse biological activities.
  • Fluorinated nucleoside analogs are crucial in antiviral and anticancer drug development.
  • Understanding the precise three-dimensional structure of such compounds is vital for drug design.

Purpose of the Study:

  • To elucidate the crystal structure of 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine.
  • To characterize the conformation of the glycosyl bond and the sugar pucker.
  • To identify and analyze the intermolecular hydrogen bonding interactions in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

Related Experiment Videos

  • The conformation of the glycosyl bond was analyzed using the chi torsion angle.
  • The furanose ring conformation was described using the Cremer-Pople parameters (P and tau).
  • Hydrogen bonding networks were identified using standard crystallographic criteria.

    • Main Results:

    • The title compound, C11H13FN4O3, was structurally characterized.
    • The glycosyl bond conformation was determined to be between anti and high anti, with chi = -101.1 (3) degrees.
    • The deoxyribose moiety adopted an S-type sugar pucker (2T3), with P = 164.7 (3) degrees and tau = 40.1 (2) degrees.
    • A three-dimensional hydrogen-bond network was observed, involving C-H...F, N-H...O, and O-H...O interactions.

    Conclusions:

    • The detailed structural analysis provides fundamental insights into the solid-state behavior of this fluorinated pyrrolo[2,3-d]pyrimidine derivative.
    • The observed hydrogen bonding network likely influences the compound's crystal packing and may have implications for its biological interactions.
    • This structural data serves as a valuable reference for the design and development of related nucleoside analogs.