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8-Chloroguanosine: solid-state and solution conformations and their biological implications.

G I Birnbaum, P Lassota, D Shugar

    Biochemistry
    |October 9, 1984
    PubMed
    Summary

    The three-dimensional structure of 8-chloroguanosine dihydrate was elucidated using X-ray crystallography and NMR spectroscopy. This study reveals key conformational details of the nucleoside, relevant to 8-substituted purine nucleoside behavior in enzymatic systems.

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    Area of Science:

    • Crystallography and structural biology
    • Nucleoside chemistry
    • Biophysical chemistry

    Background:

    • Understanding the three-dimensional structure of nucleosides is crucial for comprehending their biological roles.
    • 8-substituted purine nucleosides exhibit diverse behaviors in enzymatic systems, influenced by substituent properties.

    Purpose of the Study:

    • To determine the crystal structure of 8-chloroguanosine dihydrate.
    • To investigate the solution-state conformation of 8-chloroguanosine using NMR spectroscopy.
    • To correlate structural and conformational features with the behavior of 8-substituted purine nucleosides.

    Main Methods:

    • X-ray crystallography for solid-state structure determination.
    • Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy for solution-state conformational analysis.

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  • Direct methods and least-squares refinement for structure determination.

    • Main Results:

    • The crystal structure of 8-chloroguanosine dihydrate was determined in the orthorhombic space group P2(1)2(1)2(1).
    • The glycosidic bond conformation is syn, and the ribose exhibits a C(2')-endo pucker.
    • Solution-state NMR revealed a preference for the C(2')-endo sugar pucker and syn glycosidic bond conformation, similar to the solid state.
    • The exocyclic 5'-CH2OH group shows a moderate preference for the gauche+ rotamer in solution, unlike in the crystal.

    Conclusions:

    • The study provides detailed structural and conformational insights into 8-chloroguanosine.
    • Intramolecular hydrogen bonding in the solid state influences the 5'-CH2OH conformation, which is less pronounced in polar solution.
    • The conformational data are relevant for understanding the enzymatic interactions of 8-substituted purine nucleosides, considering steric and electronic factors.