A simple helical macrocyclic polyazapyridinophane as a stereoselective receptor of biologically important dicarboxylates under physiological conditions

Journal of Organic Chemistry

Volumn 73, Issue 2, 2008, Pages 374-382

  González Alvarez, Almudena ^a   Alfonso, Ignacio ^b   Díaz, Pilar ^c   García España, Enrique ^c   Gotor Fernández, Vicente ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

POTENTIOMETRIC TITRATIONS; STEREOSELECTIVE RECEPTOR;

AMINO ACIDS; ENANTIOSELECTIVITY; HYDROGEN BONDS; PH EFFECTS; PHYSIOLOGY; SODIUM CHLORIDE; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

AMINO ACID; ANION; ASPARTIC ACID; DICARBOXYLIC ACID; DICARBOXYLIC ACID DERIVATIVE; DRUG RECEPTOR; GLUTAMIC ACID; HYDROGEN; MACROCYCLIC COMPOUND; MALIC ACID; POLYAZAPYRIDINOPHANE; TARTARIC ACID; UNCLASSIFIED DRUG; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; PROTON; PYRIDINE DERIVATIVE; SODIUM CHLORIDE; WATER;

AQUEOUS SOLUTION; ARTICLE; BINDING KINETICS; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFORMATION; CORRELATION ANALYSIS; DRUG ACTIVITY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; GEOMETRY; HYDROGEN BOND; MASS SPECTROMETRY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NITROGEN NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PH MEASUREMENT; STEREOCHEMISTRY; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; OSMOLARITY; PH; SOLUTION AND SOLUBILITY; STEREOISOMERISM;

AZA COMPOUNDS; BINDING SITES; CARBOXYLIC ACIDS; HYDROGEN-ION CONCENTRATION; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OSMOLAR CONCENTRATION; PROTONS; PYRIDINES; SODIUM CHLORIDE; SOLUTIONS; STEREOISOMERISM; WATER;

EID: 40949093462     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701636b     Document Type: Article

References (74)

1. (a) Bianchi, A.; Bowman-James, K.; García-España, E. Supramolecular Chemistry of Anions; VCH: Weinheim, Germany, 1997.
2. (b) Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Suslick, K. S., Eds.; Pergamon: Oxford, UK, 1996.
3. (c) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
4. (d) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
5. (e) Czanik, A. W. Acc. Chem. Res. 1994, 27, 302.
6. (f) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
7. (g) Beer, P. D. Acc. Chem. Res. 1998, 31, 71.
8. (h) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192.
9. (i) Martínez-Mañez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
10. (j) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
11. For a very recent review on supramolecular chemistry in water, see: Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366.
12. (a) Lo, A. S-Y.; Liew, C.-T.; Ngai, S.-M.; Tsui, S. K.-W.; Fung, K.-P.; Lee, C.-Y.; Waye, M. M.-Y.; J. Cell. Biochem. 2005, 94, 763.
13. (b) Barshop, B. A. Mitochondrion 2004, 4, 521.
14. (a) García-España, E.; Díaz, P.; Llinares, J. M.; Bianchi, A. Coord. Chem. Rev. 2006, 250, 2952.
15. (b) Wichmann, K.; Antonioli, B.; Sohnel, T.; Wenzel, M.; Gloe, K.; Gloe, K.; Price, J. R.; Lindoy, L. F.; Blake, A. J.; Schroder, M. Coord. Chem. Rev. 2006, 250, 2987.
16. (c) Gale, P. A.; Quesada, R. Coord. Chem. Rev. 2006, 250, 3219.
17. (a) Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. J. Am. Chem. Soc. 1981, 103, 1282.
18. (b) Hosseini, M. W.; Lehn, J.-M. J. Am. Chem. Soc. 1982, 104, 3525.
19. (c) Hosseini, M. W.; Lehn, J.-M. Helv. Chim. Acta 1986, 69, 587.
20. (d) Kimura, E.; Sakonaka, A.; Yatsunami, T.; Kodama, M. J. Am. Chem. Soc. 1981, 103, 3041.
21. (e) Kimura, E.; Kodama, M.; Yatsunami, T. J. Am. Chem. Soc. 1982, 104, 3182.
22. (a) Bandell, M.; Lolkema, J. Biochemistry 2000, 39, 13059.
23. (b) Bandell, M.; Lolkema, J. Biochemistry 1999, 38, 10352.
24. For a review on enantioselective recognition of chiral anions: (a) Stibor, I.; Zlatuskova, P. Top. Curr. Chem. 2005, 255, 31.
25. For more recent selected papers: (b) Li, Z.-B.; Lin, J.; Sabat, M.; Hyacinth, M.; Pu, L. J. Org. Chem. 2007, 72, 4905.
26. (c) Peña, C.; Alfonso, I.; Tooth, B.; Voelcker, N. H.; Gotor, V. J. Org. Chem. 2007, 72, 1924.
27. (d) Miyaji, H.; Hong, S.-J.; Jeong, S.-D.; Yoon, D.-W.; Na, H.-K.; Hong, J.; Ham, S.; Sessler, J. L.; Lee C.-H. Angew. Chem., Int. Ed. 2007, 46, 2508.
28. (e) Yakovenko, A. V.; Boyko, V. I.; Kalchenko, V. I.; Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. J. Org. Chem. 2007, 72, 3223.
29. (f) González, S.; Peláez, R.; Sanz, F.; Jiménez, M. B.; Morán, J. R.; Caballero, M. C. Org. Lett. 2006, 8, 4679.
30. (g) Jadhav, V. D.; Schmidtchen, F. P. Org. Lett. 2006, 8, 2329.
31. (h) Ragusa, A.; Rossi, S.; Hayes, J. M.; Stein, M.; Kilburn, J. K. Chem. Eur. J. 2005, 11, 5674.
32. (i) Schmuk, C.; Schwegmann, M. J. Am. Chem. Soc. 2005, 127, 3373.
33. (j) Piatek, A. M.; Bomble, Y. J.; Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 6072.
34. (k) Miranda, C.; Escartí, F.; Lamarque, L.; Yunta, M. J.; Navarro, P.; García-España, E.; Jimeno, M. L. J. Am. Chem. Soc. 2004, 126, 823.
35. (l) Zheng, Y.- S.; Zhang, C. Org. Lett. 2004, 6, 1189.
36. (m) Breccia, P.; Van Gool, M.; Pérez-Fernández, R.; Martín-Santamaría, S.; Gago, F.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 2003, 125, 8270.
37. For enantioselective binding of chiral dicarboxylates in water: (a) Alfonso, I.; Dietrich, B.; Rebolledo, F.; Gotor, V.; Lehn, J. M. Helv. Chim. Acta 2001, 84, 280.
38. (b) Alfonso, I.; Rebolledo, F.; Gotor, V. Chem. Eur. J. 2000, 6, 3331.
39. González-Álvarez, A.; Alfonso, I.; Díaz, P.; García-España, E.; Gotor, V. Chem. Commun. 2006, 1227.
40. Schnarrenberger, C.; Martin, W. Eur. J. Biochem. 2002, 269, 868.
41. Demigne, C.; Sabboh, H.; Puel, C.; Remesy, C.; Coxam, V. Nutr. Res. Rev. 2004, 17, 249.
42. (a) Jane, D. E. In Medicinal Chemistry into the Millenium; Campbell, M. M., Blagbrough, I. S., Eds.; Royal Society of Chemistry: Cambridge, UK, 2001; pp 67-84.
43. (b) Standaert, D. G.; Young, A. B. In The Pharmacological Basis of Therapeutics; Hardman, J. G., Goodman Gilman, A., Limbird, L. E., Eds.; McGraw-Hill: New York, 1996; Chapter 22, p 503.
44. (c) Fletcher, E. J.; Loge, D. In An Introduction to Neurotransmission in Health and Disease; Riederer, P., Kopp, N., Pearson, J., Eds.; Oxford University Press: New York, 1990; Chapter 7, p 79.
45. (d) Childers, W. E., Jr.; Baudy, R. B. J. Med. Chem. 2007, 50, 2557.
46. (e) Schkeryantz, J. M.; Kingston, A. E.; Johnson, M. P. J. Med. Chem. 2007, 50, 2563.
47. (f) Braun-Osborne, H.; Egebjerg, J.; Nielsen, E. O.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609.
48. Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; Wiley: New York, 1995.
49. Tsukatani, T.; Matsumoto, K. Talanta 2005, 65, 396.
50. Dietrich, B.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 262.
51. Fitzsimmons, P. M.; Jackeis, S. C. Inorg. Chim. Acta 1996, 246, 301.
52. Albelda, M. T.; Bernardo, M. A.; García-España, E.; Godino-Salido, M. L.; Luis, S. V.; Melo, M. J.; Pina, F.; Soriano, C. J. Chem. Soc., Perkin Trans. 2 1999, 2545.
53. (a) Cruz, C.; Delgado, R.; Drew, M. G. B.; Félix, V. J. Org. Chem. 2007, 72, 4023.
54. (b) Hodacová, J.; Chadim, M.; Závada, J.; Aguilar, J.; García-España, E.; Luis, S. V.; Miravet, J. F. J. Org. Chem. 2005, 70, 2042.
55. (a) Flippi, A.; Gasparrini, F.; Pierini, M.; Speranza, M.; Villani, C. J. Am. Chem. Soc. 2005, 127, 11912.
56. (b) Schug, K.; Fryčák, P.; Maier, N. M.; Lindner, W. Anal. Chem. 2005, 77, 3660.
57. Geometry optimization was performed at the HF/3-21G* level of theory as implemented in Spartan 04 software.
58. The microscopic protonation sites for macrocyclic polyamines is a controversial topic, as protons can freely move around the macrocyclic structure, especially in a polar protic solvent. In this particular system, we have calculated two different protonation scheme possibilities, the one depicted in Figure 3 and that one with alternated ammonium groups (given in Figure S4 in the Supporting Information). Both optimized structures showed very similar geometries and energies, although the one in Figure 3 is more stable, probably because the distance between positive charges in the twisted helical geometry is actually larger (4.52 vs. 4.28 Å). Thus, we followed the criteria of setting the protons maximizing the distance between protonation sites, within the helical conformation. For a deeper discussion on this topic, see refs 8a and 15. A more accurate description of the real situation would be the equilibrium between all the possible protonation sites. However, as the geometry of the macrocycle is not changed by this fast prototropic process, our conformational rationale is valid using one of the structures, and we have done it for simplicity. We thank the comments from a referee who drove our attention to the need for explaining this topic.
59. (a) Pregosin, P. S. Prog. Nucl. Mag. Resort. Spectrosc. 2006, 49, 261.
60. (b) Pregosin, P. S.; Kumar, P. G. A.; Fernández, I. Chem. Rev. 2005, 105, 2977.
61. (c) Martínez-Vivente, E.; Pregosin, P. S.; Vial, L.; Herse, C.; Lacour, J. Chem. Eur. J. 2004, 10, 2912.
62. -1) was used as an internal standard for every sample. Although D values are dependent on solvent, temperature, and concentration of the sample, as the measurements were performed under the same experimental conditions for samples containing either (R)-3 or (S)-3, a direct comparison should be suitable to extract conclusions.
63. -2). Also see: Edward, J. T. J. Chem. Educ. 1970, 47, 261.
64. (a) Berova, N.; Di Bari, L.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914.
65. (b) Berova, N.; Nakanishi, K.; Woody, R. W. Circular Dichroism, Principles and Applications; Wiley-VCH: New York, 2000.
66. (a) Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313.
67. (b) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
68. (c) Pirkle, W. H.; Bocek, P. Chem. Rev. 1989, 89, 347.
69. (a) Brizard, A.; Aime, C.; Labrot, T.; Huc, I.; Berthier, D.; Artzner, F.; Desbat, B.; Oda, R. J. Am Chem. Soc. 2007, 129, 3754.
70. (b) Blondeau, P.; Segura, M.; Pérez-Fernández, R.; de Mendoza, J. Chem. Soc. Rev. 2007, 36, 198.
71. (c) Michinobu, T.; Shinoda, S.; Nakanishi, T.; Hill, J. P.; Fujii, K.; Player, T. N.; Tsukube, H.; Ariga, K. J. Am Chem. Soc. 2006, 128, 14478.
72. (d) Morino, K.; Kaptein, B.; Yashima, E. Chirality 2006, 18, 717.
73. (e) Higashi, N.; Koga, T.; Niwa, M. ChemBioChem 2002, 3, 448.
74. González-Alvarez, A.; Alfonso, I.; López-Ortiz, F.; Aguirre, A.; García-Granda, S.; Gotor, V. Eur. J. Org. Chem. 2004, 1117.