First artificial receptor for caffeine - A new concept for the complexation of alkylated oxopurines

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2472-2475

  Waldvogel, Siegfried R ^a   Fröhlich, Roland ^b   Schalley, Christoph A ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Heterocycles; Hydrogen bonds; Receptors; Supramolecular chemistry

Indexed keywords

CAFFEINE; PURINE DERIVATIVE; RECEPTOR;

ALKYLATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; MOLECULAR RECOGNITION; RECEPTOR BINDING;

EID: 0040735624     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2472::AID-ANIE2472>3.0.CO;2-F     Document Type: Article

References (16)

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10. All new compounds were obtained pure (elemental analysis (C, H, N) within ±0.4%).
11. 2, 25 C, TMS): δ = 14.15, 21.45, 22.91, 26.94, 28.68, 30.44, 31.89, 34.77, 38.51, 40.51, 57.77, 101.94, 122.37, 124.97, 147.97, 157.85.
12. The binding constants were obtained by fitting the titration curves with the Specfit program package: Specfit v.2.12, Spectrum Software Associates, Chapel Hill, NC, USA; H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1986, 33, 943, and references therein. The given error is systematical; multiple determination demonstrated an excellent reproducibility of the binding constants. A low mean variation is observed in the determined values.
13. The receptors exhibit a slight tendency to self-aggregate. The Specfit program was used to determine dimerization constants from dilution experiments. These constants have been taken into account for the fit of the binding constants. For simplicity, higher aggregates have not been included. A model including receptor trimers was tested, but including these species did not change the good agreement of measured and fitted titration curve. The constants obtained from both models are the same within the error of the experiment.
14. Syntheses of substrates; 8: R. C. Huston, W. F. Allen, J. Am. Chem. Soc. 1934, 56, 1356-1358; 9: E. Fischer, Ann. 1882, 215, 253-320.
15. Syntheses of substrates; 8: R. C. Huston, W. F. Allen, J. Am. Chem. Soc. 1934, 56, 1356-1358; 9: E. Fischer, Ann. 1882, 215, 253-320.
16. 3 close to the disordered solvate molecules, disorder refined with constraints, hydrogens calculated at the nitrogen atoms from difference fourier calculations, others calculated and refined as riding atoms. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139021. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).