The effect of substitution on protonation sites: evidence for protonation at N(3) in N(7)-substituted adenine |
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Authors: | Thomas J Kistenmacher Terumi Shigematsu Harel Weinstein |
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Institution: | Department of Chemistry, The Johns Hopkins University, Baltimore, Maryland 21218 U.S.A. |
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Abstract: | Several experimental and theoretical studies have shown that N(1) is the first site for protonation in adenine and N(9)-substituted adenine derivatives. N(7) is considered the site for the second protonation to yield dipositive cations. Results are reported here which indicate that this protonation pattern is altered in N(7)-substituted adenine derivatives. In particular, an X-ray diffraction analysis of the structure of 7-methyladenine dihydrochloride, C6N5H7]Cl2, definitively shows that the sites for protonation are N(3), as opposed to N(1), and N(9). Theoretical calculations of the molecular electrostatic potential in various systems suggest that such changes in preferred protonation sites should be expected, in general, when a modification of the molecular structure creates adjacent sites with similar reactivity, such as the N(3) and N(9) sites in 7-methyladenine. |
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Keywords: | Permanent address: Technion Haifa Israel |
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