ORGN 704 |
| Caffeine is among the most frequently consumed alkaloid compounds and omnipresent in many plants. Due to the wide range of applications for this particular alkaloid, caffeine is currently gathering increasing attention and new potential analytical tools are required. Recently, we reported the synthesis of functionalized triphenylene ketals which represent the rigid C3v symmetric scaffold for our artificial receptors (1). The cleft like structure exhibits a high affinity to caffeine and does not interfere with the alkyl groups of the oxopurine system leading to a novel concept for the molecular recognition of caffeine and related compounds. 1,3,7 Trimethyl uric acid (2) as a typical metabolite of caffeine in mammals shows an additional carbonyl group, fits better into the receptor and exhibits a significant enhanced binding. For analytical purposes of physiological fluids a clear preference for the binding of caffeine versus 2 is required. Spatial restriction of the receptor's cavity should lead to preferred binding of caffeine. In order to still obtain an exquisite affinity for the desired guest a molecular orientation of the affinity groups has to be achieved. We present the synthesis of novel anchoring groups which will allow a preferred binding of caffeine versus 1,3,7 trimethyl uric acid. The hydrogen donors are based on 1,2,3 triazole, phthalazinone, and nicotinic acid moieties.
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Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
