A combined experimental and theoretical study of the pH-dependent binding mode of NAD+ by water-soluble molecular clips

Journal of Physical Organic Chemistry

Volumn 22, Issue 8, 2009, Pages 779-790

  Polkowska, Jolanta ^a   Bastkowski, Frank ^a   Schrader, Thomas ^a   Klärner, Frank Gerrit ^a   Zienau, Jan ^b   Koziol, Felix ^b,c   Ochsenfeld, Christian ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c HARVARD UNIVERSITY   (United States)

Author keywords

Enzyme cofactors; Molecular cllps; Nucleotlde; Supramolecular chemistry

Indexed keywords

ACIDIC CONDITIONS; ACTIVE SITE; AQUEOUS SOLUTIONS; BINDING MODES; COFACTOR; COFACTORS; COMPLEX STABILITY; ENZYME COFACTORS; GUEST MOLECULES; HOST GUEST INTERACTIONS; MOLECULAR CLIPS; MOLECULAR CLLPS; NUCLEOTLDE; OXIDATION STATE; PH-DEPENDENT; PURE WATER; QUENCHING OF FLUORESCENCE; RECOGNITION PROCESS; REDOX ENZYME; SELECTIVE RECOGNITION; SELF AGGREGATION; SYNERGETIC EFFECT; THEORETICAL STUDY;

AMIDES; BINDING ENERGY; DRUG INTERACTIONS; ENZYMES; MACROMOLECULES; NUCLEIC ACIDS; QUENCHING; SUPRAMOLECULAR CHEMISTRY;

PH;

EID: 67650816136     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1519     Document Type: Article

References (36)

1. D. Voet, J. G. Voet, Biochemistry, 3rd edn, Wiley, New York, 2005.
2. A. Fersht, Structure and Mechanism in Protein Science, A Guide to Enzyme Catalysis and Protein Folding, W.H. Freeman and Company, New York, 2000.
3. Review: F.-G. Klarner, B. Kahlert, Acc. Chem. Res. 2003, 36, 919-932.
4. C. Jasper, T. Schrader, J. Panitzky, F.-G. Klaarner, Angew. Chem. Int. Ed. 2002, 41, 1355-1358.
5. -1).
6. T. Schrader, M. Fokkens, F.-G. Klärner, J. Polkowska, F. Bastkowski, J. Org. Chem. 2005, 70, 10221-10231.
7. + bisphosphate bridge: F. P. Schmidtchen, Chem. Ber. 1981, 114, 591-601.
8. H. Fenniri, M. W. Hosseini, J. M. Lehn, Helv. Chim. Acta 1997, 80, l86-803.
9. A. Domenech, E. Garcia-Espana,J. A. Ramirez, B. Celda, M. C. Martinez, D. Monleon, R.Tejero, A. Bencini, A. Bianchi, J. Chem. Soc. Perkin Trans. 2 1999, 23-32.
10. P. Talbiersky, F. Bastkowski, F.-G. Klärner, T. Schrader, J. Am. Chem. Soc. 2008, 130, 9824-9828.
11. M. Kirsch, P. Talbiersky, J. Polkowska, F. Bastkowski, T. Schaller, H. de Groot, F.-G. Klaarner, T. Schrader, in press, Angew. Chem.
12. C. Nadolny, G. Zundel, J. Mol. Struct. 1996, 385, 81-81.
13. 2O are not concentration-dependent and, hence, do not give any hint on its self-association detected by ITC.
14. F.-G. Klärner, B. Kahlert, A. Nellesen, J. Zienau, C. Ochsenfeld, T. Schrader, J. Am. Chem. Soc. 2006, 128, 4831-4841.
15. Nonlinear regression analyses of Eqns (4) and (5) were performed by the use of the program Table Curve 5.0, SPSS Science analogously to the computer program HOSTEST by Wilcox, C. S. and Glagovich, N. M., University of Pittsburgh, and the program Associate V1.6, Peterson, B. PhD Dissertation, University of California at Los Angeles, 1994. In order to determine the complex stoichiometry the experimental were analyzed with the HOSTEST program and Job plots. P. Job, C. R. Hebd. Seances Acad. Sci. 1925, 180, 925.
16. 1H NMR spectroscopy: M. Lobert, H. Bandmann, U. Burkert, U. P. Büchele, V. Podsadlowski, F.-G. Klärner, Chem.-Eur. J. 2006, 12, 1629-1641.
17. V. Balzani, H. Bandmann, P. Ceroni,C. Giansante, U. Hahn, F.-G. Klärner, U. Muller, W. M. Muller, C. Verhaelen, V. Vicinelli, F. Vögtle, J. Am. Chem. Soc. 2006, 128, 631-648.
18. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd edn, Academic Press, New York, 1971.
19. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T.Hendrickson,W.C. Still, J. Comput. Chem. 1990, 11, 440-461.
20. Macromodel, v. 1.1, Schrc)dinger, 1500 SW First Ave., Ste. 1180, Portland, OR 91201.
21. C. Ochsenfeld, J. Kussmann, F. Koziol, Angew. Chem. Int. Ed. 2004, 43, 4485-4489.
22. C. Ochsenfeld, F. Koziol, S. P. Brown, T. Schaller, U. P. Seelbach, F.-G. Klärner, Solid State Nucl. Magn. Reson. 2002, 22, 128-153.
23. Review: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
24. Cation-π interaction: J. P. Gallivan, D. A. Dougherty, J.Am. Chem. Soc. 2000, 122, 810-814.
25. Hydrophobic effect: C. Tanford, The Hydrophobic Effect, Wiley, New York, 1980.
26. Review: R. Breslow, Acc. Chem. Res. 1991, 24, 159-110.
27. Development version of the Q-Chem program package (http://www.q-chem.com) .
28. R. Ditchfield, Mol. Phys. 1974, 27, 189-801.
29. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
30. M. Häser, R. Ahlrichs, H. P. Baron, P. Weis, H. Horn, Theor. Chim. Acta 1992, 83, 455-410.
31. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2511-2511.
32. J. Kussmann, C. Ochsenfeld, J. Chem. Phys. 2007, 127, 054103.
33. M. Beer, C. Ochsenfeld, J. Chem. Phys. 2008, 128, 221102.
34. J. Zienau, J. Kussmann, F. Koziol, C. Ochsenfeld, Phys. Chem. Chem. Phys. 2007, 9, 4552-4562.
35. F. Weigend, M. Haser, H. Patzelt, R. Ahlrichs, Chem. Phys. Lett. 1998, 294, 143-152.
36. R. A. Kendall, H. A. Fruchtl, Theor. Chem. Acc. 1997, 97, 158-163.