Molecular tweezers with varying anions: A comparative study

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6721-6734

  Dutt, Som ^a   Wilch, Constanze ^a   Gersthagen, Thomas ^a   Talbiersky, Peter ^a   Bravo Rodriguez, Kenny ^b   Hanni, Matti ^c   Sánchez García, Elsa ^b   Ochsenfeld, Christian ^c   Klärner, Frank Gerrit ^a   Schrader, Thomas ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; BINDING ENERGY; CALCULATIONS; FLUORESCENCE SPECTROSCOPY; MOLECULES; NEURODEGENERATIVE DISEASES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES;

ACTIVITY OF ENZYMES; ARGININE RESIDUE; COMPARATIVE STUDIES; HYDROPHOBIC INTERACTIONS; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR TWEEZERS; PARKINSON'S DISEASE; SELECTIVE BINDING;

ENZYME INHIBITION;

AMYLOID PROTEIN; ANION; ARGININE; BENZENE; DIMER; LYSINE; PHOSPHATE; AMINO ACID; HYDROQUINONE; HYDROQUINONE DERIVATIVE; PEPTIDE; PHOSPHONIC ACID DERIVATIVE; PROTON; SOLVENT; SULFATE;

ARTICLE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CALORIMETRY; CHEMISTRY; DIMERIZATION; FLUOROMETRY; NUCLEAR MAGNETIC RESONANCE IMAGING; QUANTUM THEORY; THERMODYNAMICS; TITRIMETRY;

AMINO ACIDS; ANIONS; CALORIMETRY; DIMERIZATION; FLUOROMETRY; HYDROQUINONES; MAGNETIC RESONANCE IMAGING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOPHOSPHONATES; PEPTIDES; PHOSPHATES; PROTONS; QUANTUM THEORY; SOLVENTS; SULFATES; THERMODYNAMICS; TITRIMETRY;

EID: 84880001480     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4009673     Document Type: Article

References (64)

1. Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH Verlagsgesellschaft mbH: Weinheim, Germany
2. Lehn, J. M.; Vierling, P.; Hayward, R. J. Chem. Soc., Chem. Commun. 1979, 296-298
3. Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208-11209
4. Mandl, C. P.; König, B. J. Org. Chem. 2005, 70, 670-674
5. Douteau-Guével, N.; Coleman, A. W.; Morel, J.-P.; Morel-Desrosiers, N. J. Phys. Org. Chem. 1998, 11, 693-696
6. Douteau-Guével, N.; Coleman, A. W.; Morel, J.-P.; Morel-Desrosiers, N. J. Chem. Soc., Perkin Trans. 2 1999, 629-633
7. Douteau-Guével, N.; Perret, F.; Coleman, A. W.; Morel, J.-P. J. Chem. Soc., Perkin Trans. 2 2002, 524-532
8. Dziemidowicz, J.; Witt, D.; Rachón, J. J. Incl. Phenom. Macrocycl. Chem. 2008, 61, 381-391
9. Review: Mutihac, L.; Lee, J. H.; Kim, J. S.; Vicens, J. Chem. Soc. Rev 2011, 40, 2777-2796
10. Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192-1201
11. Bell, T. W.; Khasanov, A. B.; Drew, M. G. B.; Filikov, A.; James, T. L. Angew. Chem., Int. Ed. 1999, 38, 2543-2547
12. Öberg, C. T.; Noresson, A.-L.; Leffler, H.; Nilsson, U. J. Chem.-Eur. J. 2011, 17, 8139-8144
13. Braxmeier, T.; Demarcus, M.; Fessmann, T.; McAteer, S.; Kilburn, J. D. Chem.-Eur. J. 2001, 7, 1889-1898
14. Villari, V.; Mineo, P.; Scamporrino, E.; Micali, N. Chem. Phys. 2012, 402, 118-123
15. Fokkens, M.; Schrader, T.; Klärner, F.-G. J. Am. Chem. Soc. 2005, 127, 14415-14421
16. Talbiersky, P.; Bastkowski, F.; Klärner, F.-G.; Schrader, T. J. Am. Chem. Soc. 2008, 130, 9824-9828
17. Sinha, S.; Lopes, D. H. J.; Du, Z.; Pang, E. S.; Shanmugam, A.; Lomakin, A.; Talbiersky, P.; Tennstaedt, A.; McDaniel, K.; Bakshi, R.; Kuo, P.-Y.; Ehrmann, M.; Benedek, G.-B.; Loo, J. A.; Klärner, F.-G.; Schrader, T.; Wang, C.; Bitan, G. J. Am. Chem. Soc. 2011, 133, 16958-16969
18. Sinha, S.; Du, Z.; Maiti, P.; Klärner, F.-G.; Schrader, T.; Wang, C.; Bitan, G. ACS Chem. Neurosci. 2012, 3 (6) 451-458
19. Prabhudesai, S.; Sinha, S.; Attar, A.; Kotagiri, A.; Fitzmaurice, A. G.; Lakshmanan, R.; Ivanova, M. I.; Loo, J. A.; Klärner, F.-G.; Schrader, T.; Stahl, M.; Bitan, G.; Bronstein, J. M. Neurotherapeutics 2012, 9, 464-476
20. Review: Klärner, F.-G.; Schrader, T. Acc. Chem. Res. 2013, 46, 967-978
21. Bier, D.; Rose, R.; Bravo-Rodriguez, K.; Bartel, M.; Ramirez-Anguita, J. M.; Dutt, S.; Wilch, C.; Klärner, F.-G.; Sanchez-Garcia, E.; Schrader, T.; Ottmann, C. Nat. Chem. 2013, 5, 234-239
22. Klärner, F.-G.; Burkert, U.; Kamieth, M.; Boese, R.; Benet-Buchholz, J. Chem.-Eur. J. 1999, 5, 1700-1707
23. 2Et): Klärner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 1130-1133
24. +-substituted tweezer, which is analogous to 1d, was prepared by Klärner, F.-G.; Burkert, U.; Kamieth, M.; Boese, R. J. Phys. Org. Chem. 2000, 604-611
25. Klärner, F.-G.; Kahlert, B.; Nellesen, A.; Zienau, J.; Ochsenfeld, C.; Schrader, T. J. Am. Chem. Soc. 2006, 128, 4831-4841
26. J. Am. Chem. Soc. 2010, 132, 4029.
27. Review. Interaction of KAA with vancomycin: Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193
28. Tjernberg, L. O.; Lilliehook, C.; Callaway, D. J. E.; Naslund, J.; Hahne, S.; Thyberg, J.; Terenius, L.; Nordstedt, C. J. Biol. Chem. 1997, 272, 12601-12605
29. Guttman, C. Dermatol. Times 2002, Sept 1.
30. Hynes, R. O. Cell 1992, 69, 11-25
31. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187-217
32. Mackerell, A. D.; Feig, M.; Brooks, C. L. J. Comput. Chem. 2004, 25, 1400-1415
33. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935
34. Zoete, V.; Cuendet, M. A.; Grosdidier, A.; Michielin, O. J. Comput. Chem. 2011, 32, 2359-2368
35. Chemshell, a Computational Chemistry Shell (www.chemshell.org).
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
37. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
38. Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
39. Senn, H. M.; Thiel, W. Angew. Chem. I. E. 2009, 48, 1198-1229
40. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
41. Development version of the Q-Chem program package, 2012, (http://www.q-chem.com).
42. London, F. J. Phys. Radium 1937, 8, 397-409
43. Ditchfield, R. Mol. Phys. 1974, 27, 789
44. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260
45. Zienau, J.; Kussmann, J.; Koziol, F.; Ochsenfeld, C. Phys. Chem. Chem. Phys. 2007, 9, 4552-4562
46. Zienau, J.; Kussmann, J.; Ochsenfeld, C. Mol. Phys. 2010, 108, 333-342
47. Polkowska, J.; Bastkowski, F.; Schrader, T.; Klärner, F.-G.; Zienau, J.; Koziol, F.; Ochsenfeld, C. J. Phys. Org. Chem. 2009, 22, 779-790
48. Flaig, D.; Beer, M.; Ochsenfeld, C. J. Chem. Theory Comput. 2012, 8, 2260-2271
49. Ochsenfeld, C.; Kussmann, J.; Koziol, F. Angew. Chem., Int. Ed. 2004, 43, 4485-4489
50. Kussmann, J.; Ochsenfeld, C. J. Chem. Phys. 2007, 127, 054103
51. Beer, M.; Ochsenfeld, C. J. Chem. Phys. 2008, 128, 221102
52. Beer, M.; Kussmann, J.; Ochsenfeld, C. J. Chem. Phys. 2011, 134, 074102
53. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297
54. Bühl, M.; Mauschick, F. T. Phys. Chem. Chem. Phys. 2002, 4, 5508-5514
55. Bühl, M.; Parrinello, M. Chem.-Eur. J. 2001, 7, 4487-4494
56. Pennanen, T. S.; Vaara, J.; Lantto, P.; Sillanpää, A. J.; Laasonen, K.; Jokisaari, J. J. Am. Chem. Soc. 2004, 126, 11093-11102
57. Kongsted, J.; Nielsen, C. B.; Mikkelsen, K. V.; Christiansen, O.; Ruud, K. J. Chem. Phys. 2007, 126, 034510-1-034510-8
58. Aidas, K.; Møgelhøj, A.; Nielsen, C. B.; Mikkelsen, K. V.; Ruud, K.; Christiansen, O.; Kongsted, J. J. Phys. Chem. A 2007, 111, 4199-4210
59. Aidas, K.; Mikkelsen, K. V.; Kongsted, J. Phys. Chem. Chem. Phys. 2009, 12, 761-768
60. Bulo, R. E.; Jacob, C. R.; Visscher, L. J. Phys. Chem. A 2008, 112, 2640-2647
61. Klärner, F.-G; Panitzky, J.; Bläser, D.; Boese, R. Tetrahedron 2001, 3673-3687
62. Klärner, F.-G.; Polkowska, J.; Panitzky, J.; Seelbach, U. P.; Burkert, U.; Kamieth, M.; Baumann, M.; Wigger, A. E.; Boese, R.; Blaeser, D. Eur. J. Org. Chem. 2004, 7, 1405-1423
63. Gallivan, J. P.; Dougherty, D. A. J. Am. Chem. Soc. 2000, 122, 870-874
64. Ruloff, R.; Seelbach, U. P.; Merbach, A. E.; Klärner, F.-G. J. Phys. Org. Chem. 2002, 15, 189-196 and references therein