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1H- and 13C-nmr studies on caffeine and its interaction with nucleic acids
Authors:Lou-sing Kan  Philip N. Borer  Doris M. Cheng  Paul O. P. Ts'o
Abstract:The relative orientation of caffeine in stacks formed by self-association in aqueous solution has been evaluated by both 1H- and 13C-nmr spectroscopy. The data, which were interpreted through the calculation of ring-current and atomic diamagnetic anisotropic effects of the caffeine molecule, suggest two caffeine bases may stack in a nearly orthogonal manner. The interactions between caffeine and adenylyl-3′,5′-adenosine, polyadenylic acid, and ribo-(A-A-G-C-U-U)2 helix were also studied by nmr at different caffeine/base ratios and at varying temperatures. The results show that caffeine tends to stack on the top of the terminal purine bases or to insert (the single-stranded) or to intercalate (the double-stranded) between purine bases.
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