Recognition of Caffeine in Aqueous Solutions


Fiammengo, Roberto and Crego-Calama, Mercedes and Timmerman, Peter and Reinhoudt, David N. (2003) Recognition of Caffeine in Aqueous Solutions. Chemistry: a European journal, 9 (3). pp. 784-792. ISSN 0947-6539

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Abstract:Binding of caffeine in aqueous solutions has been achieved for the first time by using water-soluble, tetracationic peptide-porphyrin conjugates Zn-1 as the receptor molecules. The association constant for caffeine with receptor Zn-1 is in some cases as high as 6000 M-1, only 5-6 times lower than the highest binding constant reported for an artificial caffeine receptor in low polarity aprotic solvents. The binding mechanism has been studied by a combination of experimental techniques such as UV-visible and NMR spectroscopy and microcalorimetry. Recognition of caffeine involves both stacking with the porphyrin ring and metal coordination. Subtle variations of the receptor structure affect the complexation. Receptors Zn-1 have also been investigated for the recognition of molecules structurally related to caffeine, for example, 1-methylimidazole. Selectivity towards oxopurine derivatives (caffeine and theophylline) have been found.
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Copyright:© 2003 Wiley InterScience
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Metis ID: 215563