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  • Title: The conformational effect of para-substituted C8-arylguanine adducts on the B/Z-DNA equilibrium.
    Author: Vongsutilers V, Phillips DJ, Train BC, McKelvey GR, Thomsen NM, Shaughnessy KH, Lewis JP, Gannett PM.
    Journal: Biophys Chem; 2011 Feb; 154(1):41-8. PubMed ID: 21255902.
    Abstract:
    The B form of DNA exists in equilibrium with the Z form and is mainly affected by sequence, electrostatic interactions, and steric effects. C8-purine substitution shifts the equilibrium toward the Z form though how this interaction overcomes the unfavorable electrostatic interactions and decrease in stacking in the Z form has not been determined. Here, a series of C8-arylguanine derivatives, bearing a para-substituent were prepared and the B/Z equilibrium determined. B/Z ratios were measured by CD and conformational effects of the aryl substitution determined by NMR spectroscopy and molecular modeling. The para-substituent was found to have a significant effect on the B/Z DNA equilibrium caused by altering base-pair stacking of the B form and modifying the hydration/ion shell of the B form. A unique melting temperature versus salt concentration was observed and provides evidence relevant to the mechanism of B/Z conformational interconversion.
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