The role of intramolecular hydrogen bonding on nucleobase acidification following metal coordination: possible implications of an "indirect" role of metals in acid-base catalysis of nucleic acids
The acidifying effect of Pt(II) on nucleobase -NH and -NH2 groups depends both on the site of metal coordination and on the efficiency of stabilization of the deprotonated nucleobase via intracomplex hydrogen bonding. Weakly acidic nucleobase protons with pK (a) values between 9 and 17 can be acidif...
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| Veröffentlicht in: | Journal of biological inorganic chemistry 2005-11, Vol.10 (7), p.800-812 |
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| container_title | Journal of biological inorganic chemistry |
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| creator | Roitzsch, Michael Añorbe, Marta Garijo Miguel, Pablo J Sanz Müller, Barbara Lippert, Bernhard |
| description | The acidifying effect of Pt(II) on nucleobase -NH and -NH2 groups depends both on the site of metal coordination and on the efficiency of stabilization of the deprotonated nucleobase via intracomplex hydrogen bonding. Weakly acidic nucleobase protons with pK (a) values between 9 and 17 can be acidified by a single Pt(II) to have pK (a) values which are well within the physiological pH range. This could open the possibility of an acid-base catalysis occurring at pH 7, with the metal-nucleobase entity functioning either as an acid or a base. Examples of Pt(II) complexes studied here include, among others, mixed nucleobase systems of 1-methylcytosine and 1,9-dimethyladenine as well as a complex of the rare iminooxo tautomer of 1-methylcytosine having the metal bonded at N4. |
| doi_str_mv | 10.1007/s00775-005-0030-4 |
| format | Article |
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Weakly acidic nucleobase protons with pK (a) values between 9 and 17 can be acidified by a single Pt(II) to have pK (a) values which are well within the physiological pH range. This could open the possibility of an acid-base catalysis occurring at pH 7, with the metal-nucleobase entity functioning either as an acid or a base. 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| identifier | ISSN: 0949-8257 |
| ispartof | Journal of biological inorganic chemistry, 2005-11, Vol.10 (7), p.800-812 |
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| language | eng |
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| source | MEDLINE; SpringerLink Journals |
| subjects | Catalysis Crystallography, X-Ray Cytosine - analogs & derivatives Cytosine - chemistry Hydrogen Bonding Hydrogen-Ion Concentration Magnetic Resonance Spectroscopy Metals - chemistry Models, Molecular Nucleic Acids - chemistry Nucleotides - chemistry |
| title | The role of intramolecular hydrogen bonding on nucleobase acidification following metal coordination: possible implications of an "indirect" role of metals in acid-base catalysis of nucleic acids |
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