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Related Experiment Videos

3,5'-Anhydrosynadenol: A Polycyclic Anhydronucleoside Analogue.

Yao-Ling Qiu1, Jiri Zemlicka1

  • 1Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, 110 E. Warren Ave., Detroit, MI 48201-1379 (USA), Fax: (+1) 313-832-7294.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary

Antiviral nucleoside analogue 1 undergoes cyclization with phosphorylating agents, forming a novel polycyclic compound 2. This reaction confirms the Z configuration of compound 1, crucial for its antiviral properties.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Virology

Background:

  • Antiviral nucleoside analogues are critical in treating viral infections.
  • Understanding the stereochemistry of these analogues is vital for their efficacy.
  • The reaction pathways of nucleoside analogues with phosphorylating agents require detailed investigation.

Purpose of the Study:

  • To investigate the reaction of antiviral nucleoside analogue 1 with highly reactive phosphorylating agents.
  • To characterize the resulting products and elucidate their formation mechanisms.
  • To confirm the stereochemical configuration of nucleoside analogue 1.

Main Methods:

  • Reaction of nucleoside analogue 1 with phosphorylating agents.
  • Characterization of the novel polycyclic compound 2 using spectroscopic techniques.
Keywords:
Antiviral agentsCyclizationsNucleoside analoguesSmall ring systems

Related Experiment Videos

  • Stereochemical analysis to determine the configuration of compound 1.

    • Main Results:

    • Cyclization occurred instead of the expected O-phosphorylation.
    • A novel polycyclic compound, designated as 2, was successfully synthesized.
    • The formation of compound 2 confirmed that nucleoside analogue 1 possesses the Z configuration.

    Conclusions:

    • The reaction of antiviral nucleoside analogue 1 with phosphorylating agents leads to cyclization, not O-phosphorylation.
    • The Z configuration of nucleoside analogue 1 is essential for its antiviral activity and that of related compounds.
    • This study provides insights into the chemical behavior of antiviral nucleoside analogues.