Size-tunable trehalose-based nanocavities: Synthesis, structure, and inclusion properties of large-ring cyclotrehalans

Journal of Organic Chemistry

Volumn 74, Issue 8, 2009, Pages 2997-3008

  Rodríguez Lucena, David ^a   Mellet, Carmen Ortiz ^a   Jaime, Carlos ^b   Burusco, Kepa K ^b   Fernández, José M García ^c   Benito, Juan M ^c  

^a UNIVERSITY OF SEVILLE   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BULK SOLVENTS; CAVITY SIZES; CDS; EFFICIENT STRATEGIES; GLUCOPYRANOSIDE; GLYCOSIDIC LINKAGES; INCLUSION PROPERTIES; MACROCYCLIZATION REACTIONS; NANO-CAVITIES; NANOMETRIC;

GLUCOSE; MOLECULAR MECHANICS; OLIGOMERS; POLYMERS; POLYSACCHARIDES;

DATA STORAGE EQUIPMENT;

CYCLODEXTRIN DERIVATIVE; CYCLOTREHALAN; MONOSACCHARIDE; PENTAKIS[N,N' BIS (2,3,4,2',3',4' HEXA O ACETYL 6,6' DIDEOXY ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; PENTAKIS[N,N' BIS (6,6' DIDEOXY 2,3,4,2',3',4' HEXA O TRIMETHYSILYL ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; PENTAKIS[N,N' BIS (6,6' DIDEOXY ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; SOLVENT; TETRAKIS[N,N' BIS (2,3,4,2',3',4' HEXA O ACETYL 6,6' DIDEOXY ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; TETRAKIS[N,N' BIS (6,6' DIDEOXY 2,3,4,2',3',4' HEXA O TRIMETHYLSILYL ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; TETRAKIS[N,N' BIS (6,6' DIDEOXY ALPHA,ALPHA' TREHALOS 6,6' DIYL)]THIOUREA; TREHALOSE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CYCLIZATION; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; OLIGOMERIZATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

AMIDES; CYCLIZATION; CYCLODEXTRINS; DISACCHARIDES; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; TREHALOSE;

EID: 65449154004     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802796p     Document Type: Article

References (85)

1. (a) Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
2. (b) Cooke, G. Angew. Chem. 2003, 115, 5008; Angew. Chem., Int. Ed. 2003, 42, 4860.
3. Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds. Comprehensive Supramolecular Chemistry; Elsevier: Oxford, U.K., 1996; Vols. 1-11.
4. For a comprehensive review on cyclodextrins, see: Szejtli, J. Chem. Rev. 1998, 98, 1743.
5. For review papers, see: (a) Svoboda, J.; König, B. Chem. Rev. 2006, 106, 5413.
6. (b) Takahashi, K. Chem. Rev. 1998, 98, 2013.
7. For recent publications, see: (a) Yang, C.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 5786.
8. (b) Lu, R.; Yang, C; Cao, Y.; Wang, Z.; Wada, T.; Jiao, W.; Mori, T.; Inoue, Y. Chem. Commun. 2008, 374.
9. (c) Senra, J. D.; Malta, L. F. B.; de Souza, A. L. F.; Medeiros, M. E.; Aguiar, L. C. S.; Antunes, O. A. C. Tetrahedron Lett. 2007, 48, 8153.
10. For a recent review, see: Vyas, A.; Saraf, S.; Saraf, S. J. Incl. Phenom. Macro. 2008, 62, 23.
11. (a) Hattori, K.; Kenmoku, A.; Mizuguchi, T.; Ikeda, D.; Mizuno, M.; Inazu, T. J. Incl. Phenom. Macro. 2006, 56, 9.
12. (b) Benito, J. M.; Gómez-García, M.; Ortiz Mellet, C; Baussanne, I.; Defaye, J.; García Fernández, J. M. J. Am. Chem. Soc. 2004, 126, 10355.
13. (c) Mazzaglia, N.; Forde, D.; Garozzo, D.; Malvagna, P.; Ravoo, B. J.; Darcy, R. Org. Biomol. Chem. 2004, 2, 957.
14. (d) Ortiz Mellet, C.; Defaye, J.; García Fernández, J. M. Chem.-Eur. J. 2002, 8, 1982.
15. For a review, see: Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088.
16. (a) Yuan, D.-Q.; Kitagawa, Y.; Aoyama, Y.; Douke, T.; Fukudome, M.; Fujita, K. Angew. Chem., Int. Ed. 2007, 46, 5024.
17. (b) Bjerre, J.; Nielsen, E. H.; Bols, M. Eur. J. Org. Chem. 2007, 745.
18. (c) Bjerre, J.; Fenger, T. H.; Marinescu, L. G.; Bols, M. Eur. J. Org. Chem. 2007, 704.
19. (d) Marinescu, L. G.; Bols, M. Angew. Chem., Int. Ed. 2006, 45, 4590.
20. (e) Ortega-Caballero, F.; Rousseau, C.; Christensen, B.; Petersen, T. E.; Bols, M. J. Am. Chem. Soc. 2005, 127, 3238.
21. (a) Zhou, Y.-H.; Zhao, M.; Mao, Z.-W.; Ji, L.-N. Chem.-Eur. J. 2008, 14, 7193.
22. (b) Dong, Z.-Y.; Mao, S.-Z.; Liang, K.; Liu, J.-Q.; Luo, G.-M.; Shen, J.-C. Chem.-Eur. J. 2006,12, 357.
23. (d) Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106,767.
24. (c) Jeunesse, C.; Armspach, D.; Matt, D. Chem. Commun. 2005, 5603.
25. For areview, see: Wenz, G.; Han, B. H.; Muller, A. Chem. Rev. 2006, 106, 782.
26. (a) Zhao, Y. L.; Dichtel, W. R.; Trabolsi, A.; Saha, S.; Aprahamian, I.; Stoddart, J. F. J. Am. Chem. Soc. 2008, 130, 11294.
27. (b) Wang, Y.; Ma, N.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 546.
28. (c) Coulston, R. J.; Onagi, H.; Lincoln, S. F.; Easton, C. J. J. Am. Chem. Soc. 2006, 128, 14750.
29. (d) Tian, H.; Wang, Q. C. Chem. Soc. Rev. 2006, 35, 364.
30. (e) Smiljanic, N.; Moreau, V.; Yockot, D.; Benito, J. M.; García Fernández, J. M.; Djedaïni-Pilard, F. Angew. Chem., Int. Ed. 2006, 45, 546.
31. (a) Zhang, L.; Wu, Y.; Brunsveld, L. Angew. Chem., Int. Ed. 2007, 46, 1798.
32. (b) Medintz, I. L.; Clapp, A. R.; Mattoussi, H.; Goldman, E. R.; Fisher, B.; Mauro, J. M. Nat. Mater. 2003, 2, 630.
33. (c) Tong, A. J.; Yamauchi, A.; Hayashita, T.; Zhang, Z.-Y.; Smith, B. D.; Teramae, N. Anal. Chem. 2001, 73, 1530.
34. For technological applications, see: (a) Skriba, G. K. E. J. Sep. Sci. 2008, 31, 1991.
35. (b) Araki, J.; Ito, K. Soft Matter 2008, 3, 1456.
36. (c) Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vötgel, F., Eds. Comprehensive Supramolecular Chemistry; Elsevier: Oxford, U.K., 1996; Vol. 3.
37. For pharmaceutical and biomedical applications, see: (a) Davis, M. E.; Brewster, M. E. Nat. Rev. Drug Discovery 2004, 3, 1023.
38. (b) Li, J.; Loh, X. J. Adv. Drug. Delivery Rev. 2008, 60, 1000.
39. (c) Cal, K.; Centkowska, K. Eur. J. Pharm. Biopharm. 2008, 68, 467.
40. (d) Carrier, R. L.; Miller, L. A.; Ahmed, I. J. Control. Release 2007, 123, 78.
41. (a) Fukudome, M.; Shiratani, T.; Nogami, Y.; Yuan, D.-Q.; Fujita, K. Org. Lett. 2006, 8, 5733.
42. (b) Fukudome, M.; Shiratani, T.; Immel, S.; Nogami, Y.; Yuan, D.-Q.; Fujita, K. Angew. Chem., Int. Ed. 2005, 44, 4201.
43. (c) Nogami, Y.; Nasu, K.; Koga, T.; Ohta, K.; Fujita, K.; Immel, S.; Lindner, H. J.; Schmitt, G E.; Lichtenthaler, F. W. Angew. Chem., Int. Ed. 1997, 36, 1899.
44. (d) Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78.
45. Gatuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919.
46. Fan, L.; Hinsgaul, O. Org. Lett. 2002, 4, 4503.
47. Bürli, R.; Vasella, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1852.
48. (a) Ménand, M.; Blais, J.-C.; Hamon, L.; Valéry, J.-M.; Xie, J. J. Org. Chem. 2005, 70, 4423.
49. (b) Van Well, R. M.; Marinelli, L.; Erkelens, K.; van der Marel, G. A.; Lavecchia, A.; Overkleeft, H. S.; van Boom, J. H.; Kessler, H.; Overhand, M. Eur. J. Org. Chem. 2003, 2303.
50. (c) Locardi, E.; Stöckle, M.; Gruner, S.; Kessler, H. J. Am. Chem. Soc. 2001, 123, 8189.
51. Ménand, M.; Blais, J.-C; Valéry, J.-M.; Xie, J. J. Org. Chem. 2006, 71, 3295.
52. (a) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638.
53. (b) Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 1371.
54. (a) Di Fabio, G.; Randazzo, A.; D'Onofrio, J.; Ausín, C.; Pedroso, E.; Grandas, A.; De Napoli, L.; Montesarchio, D. J. Org. Chem. 2006, 71, 3395.
55. (b) Coppola, C.; Aggiomo, V.; Di Fabio, G.; De Napoli, L.; Montesarchio, D. J. Org. Chem. 2007, 72, 9679.
56. (c) D'Onofrio, J.; Coppola, C; Di Fabio, G.; De Napoli, L.; Montesarchio, D. Eur. J. Org. Chem. 2007, 3849.
57. García Fernández, J. M.; Ortiz Mellet, C; Defaye, J. J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 149.
58. (a) García Fernández, J. M.; Jiménez Blanco, J. L.; Ortiz Mellet, C.; Fuentes Mota, J. J. Chem. Soc, Chem. Commun. 1995, 57.
59. (b) Jiménez Blanco, J. L.; Benito, J. M.; Ortiz Mellet, C; García Fernández, J. M. Org. Lett. 1999, 1, 1217.
60. (c) Benito, J. M.; Jiménez Blanco, J. L.; Ortiz Mellet, C.; García Fernández, J. M. Angew. Chem., Int. Ed. 2002, 41, 3674.
61. Rodríguez-Lucena, D.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M. J. Incl. Phenom. Macro. 2007, 57, 147.
62. Rodríguez-Lucena, D.; Benito, J. M.; Álvarez, E.; Jaime, C; Pérez- Mirón, J.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2008, 73, 2967.
63. Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45.
64. García-Moreno, M. I.; Díaz-Pérez, P.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2003, 68, 8890.
65. (a) Jiménez Blanco, J. L.; García Fernández, J. M.; Gadelle, A.; Defaye, J. Carbohydr. Res. 1997, 303, 367.
66. (b) García Fernández, J. M.; Ortiz Mellet, C; Jiménez Blanco, J. L.; Fuentes Mota, J.; Gadelle, A.; Coste-Sarguet, A.; Defaye, J. Carbohydr. Res. 1995, 268, 57.
67. Jiménez Blanco, J. L.; Saitz-Barría, C.; Benito, J. M.; Ortiz Mellet, C.; Fuentes, J.; Santoyo-González, F.; García Fernández, J. M. Synthesis 1999, 1907.
68. Katajisto, J.; Karskela, T.; Heinonen, P.; Lönnberg, H. J. Org. Chem. 2002, 67, 7995.
69. Acetylation of thiourea adducts must be conducted at temperatures lower than 0 °C to prevent formation of N- or S-acetyl derivatives. See: García-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M. Tetrahedron: Asymmetry 2000, 11, 161.
70. (a) Ortiz Mellet, C; Moreno Marín, A.; Jiménez Blanco, J. L.; García Fernández, J. M.; Fuentes, J. Tetrahedron: Asymmetry 1994, 5, 2325.
71. (b) Ortiz Mellet, C; García Fernández, J. M. Sulfur Rep. 1996, 19, 61.
72. (c) Ortiz Mellet, C; García Fernandez, J. M. Adv. Carbohydr. Chem. Biochem. 2000, 55, 35.
73. Saenger, W.; Jacob, J.; Gessler, K.; Steiner, T.; Hoffmann, D.; Sanbe, H.; Koizumi, K.; Smith, S. M.; Takaha, T. Chem. Rev. 1998, 98, 1787.
74. (a) Kirschner, K. N.; Woods, R. J. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 10541.
75. (b) Bock, K.; Duus, J. J. Carbohydr. Chem. 1994, 13, 513.
76. For a complete survey on complexation thermodynamics of CDs, see: Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
77. The authors kindly thank Dr. C. Hunter for providing the titration isotherm curve fitting program. For a detailed description of the fitting methods and equations, see: (a) Bisson, A. P. Hunter, C. A. Morales, J. C. Young, K. Chem.-Eur. J. 1998, 4, 845.
78. (b) Bisson, A. P. Carver, F. J. Eggleston, D. S. Haltiwanger, R. C. Hunter, C. A. Livingston, D. L. McCabe, J. F. Rotger, C. Rowan, A. E. J. Am. Chem. Soc. 2000, 122, 8856. Errors are estimated to be in the range of ±15%.
79. Cromwell, W. C.; Bystrom, K.; Eftink, M. R. J. Phys. Chem. 1985, 89, 326.
80. Turner, D. C; Brand, L. Biochemistry 1968, 7, 3381.
81. Recent studies of noncovalent binding in supramolecular complexes by ESI-MS/MS revealed that interactions existing in the gas phase are relatively reflective of their solution behavior. See: Nesatyy, V. J. Int. J. Mass Spectrom. 2002, 221, 147.
82. The 1:1 complex stoichiometry was confirmed by the continuous variation method (Job plot). For a thorough description, see: (a) Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley: Chichester, U.K., 1987. (b) Job, P. Ann. Chim. 1928, 9, 113.
83. These results parallel those reported for the CD series. See: Schneider, H.-J.; Blatter, T; Simova, S. J. Am. Chem. Soc. 1991, 113, 1996.
84. Binding constants were obtained at 32 °C in phosphate buffered media (10 mM, pH 7.3). Errors are estimated to be in the range of ±15%.
85. Franke, J.; Merz, F.; Lorenski, H. W.; Muller, W. M.; Werner, W.; Vogtle, F. J. Inclusion Phenom. 1985, 3, 471.