Summary
The direct chemical interaction of catecholamines with adenine nucleotides has been examined using the technique of nuclear magnetic resonance spectroscopy. Preferential stabilization of the alpha and beta carbons of the side chain of epinephrine has been demonstrated by selective changes in the relaxation times of the protons attached to these carbons. By varying the concentrations of amine and nucleotide, it has been shown that at pH 5.6, three molecules of epinephrine can interact with one molecule of ATP and one molecule of epinephrine can interact with one molecule of AMP. An additional catecholamine molecule may be attached to the adenine nucleotide complexes at a higher pH. The complex appears to involve an ionic bond between the catecholamine nitrogen and the phosphate moiety of the nucleotide and a hydrogen bond between the beta hydroxyl group of the catecholamine and a phosphate oxygen. The very small preferential stabilization of the side chain carbons of dopamine in the presence of ATP indicates that the beta hydroxyl group of the catecholamine plays a role in the interaction.
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Dedicated to Professor Otto Krayer on the occasion of his 65th birthday.
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This work was supported by grants GM-09591 and NB-02947 from the National Institutes of Health, grants GB-578 and GB-19296 from the National Science Foundation and U.S. Air Force Contract 41(657)-414.
We wish to acknowledge the assistance of Dr. Peter Pappas during the initial stages of this investigation, and the assistance of Mrs. Kriemhild Koenig and Miss Norma Wade.
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Weiner, N., Jardetzky, O. A study of catecholamine nucleotide complexes by nuclear magnetic resonance spectroscopy. Naunyn - Schmiedebergs Arch 248, 308–318 (1964). https://doi.org/10.1007/BF00246348
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DOI: https://doi.org/10.1007/BF00246348