Synthesis, structure, and inclusion capabilities of trehalose-based cyclodextrin analogues (cyclotrehalans)

Journal of Organic Chemistry

Volumn 73, Issue 8, 2008, Pages 2967-2979

  Rodríguez Lucena, David ^a   Benito, Juan M ^b   Álvarez, Eleuterio ^b   Jaime, Carlos ^c   Perez Miron, Javier ^c   Mellet, Carmen Ortiz ^a   García Fernández, José M ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN; CYCLOOLIGOSACCHARIDES; HYDROPHOBIC CAVITY; PSEUDOAMIDE SEGMENTS;

CRYSTAL SYMMETRY; HYDROPHOBICITY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RIGIDITY; SYNTHESIS (CHEMICAL);

OLIGOSACCHARIDES;

6 (4 TOLUIDINO)NAPHTHALENE 2 SULFONATE; 8 ANILINO 1 NAPHTHALENESULFONIC ACID; ADAMANTANE; CARBOXYLIC ACID DERIVATIVE; CYCLODEXTRIN DERIVATIVE; CYCLOTREHALAN DERIVATIVE; DISACCHARIDE; MONOSACCHARIDE; NAPHTHALENE DERIVATIVE; OLIGOSACCHARIDE; TREHALOSE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CARBODIIMIDES; CYCLODEXTRINS; GUANIDINE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; TREHALOSE;

EID: 42349095247     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800048s     Document Type: Article

References (77)

1. Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vötgel, F., Eds. Comprehensive Supramolecular Chemistry; Elsevier: Oxford, 1996; Vol. 1-11.
2. For a comprehensive review on cyclodextrins, see: Szejtli, J. Chem. Rev. 1998, 98, 1743.
3. Takahashi, K. Chem. Rev. 1998, 98, 2013.
4. (a) Hattori, K.; Kenmoku, A.; Mizuguchi, T.; Ikeda, D.; Mizuno, M.; Inazu, T. J. Incl. Phenom. Macrocycl. Chem. 2006, 56, 9.
5. (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.
6. (c) Mazzaglia, N.; Forde, D.; Garozzo, D.; Malvagna, P.; Ravoo, B. J.; Darcy, R. Org. Biomol. Chem. 2004, 2, 957.
7. (d) Ortiz, Mellet, C.; Defaye, J.; García Fernández, J. M. Chem. Eur. J. 2002, 8, 1982.
8. (a) Marinescu, L. G.; Bols, M, Angew. Chem., Int. Ed. 2006, 45, 4590.
9. (b) Ortega-Caballero, F.; Rousseau, C.; Christensen, B.; Petersen, T. E.; Bols, M. J. Am. Chem. Soc. 2005, 127, 3238.
10. (c) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
11. (a) Dong, Z.-Y.; Mao, S.-Z.; Liang, K.; Liu, J.-Q.; Luo, G.-M.; Shen, J.-C. Chem. Eur. J. 2006, 12, 357.
12. (b) Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106, 767.
13. (c) Jeunesse, C.; Armspach, D.; Matt, D. Chem. Commun. 2005, 5603.
14. (a) Coulston, R. J.; Onagi, H.; Lincoln, S. F.; Easton, C. J. J. Am. Chem. Soc. 2006, 128, 14750.
15. (b) Tian, H.; Wang, Q. C. Chem. Soc. Rev. 2006, 35, 364.
16. (c) Wenz, G.; Han, B. H.; Muller, A. Chem. Rev. 2006, 106, 782.
17. (a) Zhang, L.; Wu, Y.; Brunsveld, L. Angew. Chem., Int. Ed. 2007, 46, 1798.
18. (b) Smiljanic, N.; Moreau, V.; Yockot, D.; Benito, J. M.; García Fernández, J. M.; Djedaïni-Pilard, F. Angew. Chem., Int. Ed. 2006, 45, 546.
19. (a) Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977.
20. (b) Engeldinger, E.; Armspach, Matt, D. D. Chem. Rev. 2003, 103, 4147.
21. (c) Lecourt, T.; Herault, A.; Pearce, A. J.; Sollogoub, M.; Sinay, P. Chem. Eur. J. 2004, 10, 2960.
22. (a) Fujita, K.; Shimada, H.; Ohta, K.; Nogami, Y.; Nasu, K.; Koga, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1621.
23. (b) 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. Engl. 1997, 36, 1899.
24. (c) Yang, C.; Yuan, D.-Q.; Nogami, Y.; Fujita, K. Tetrahedron Lett. 2003, 44, 4641.
25. (d) Lindner, H. J.; Lichtenthaler, F. W.; Fujita, K.; Yang, C.; Yuan, D.-Q.; Nogami, Y. Acta Crystallogr. Sect. E 2003, 59, 387.
26. Yuan, D.-Q.; Tahara, T.; Chen, W.-H.; Okabe, Y.; Yang, C.; Yagi, Y.; Nogami, Y.; Fukudome, M.; Fujita, K. J. Org. Chem. 2003, 68, 9456.
27. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78.
28. Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919.
29. Fan, L.; Hindsgaul, O. Org. Lett. 2002, 4, 4503.
30. Bürli, R.; Vasella, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1852.
31. (a) Ménand, M.; Blais, J.-C.; Hamon, L.; Valéry, J.-M.; Xie, J. J. Org. Chem. 2005, 70, 4423.
32. (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.
33. (c) Locardi, E.; Stöckle, M.; Gruner, S.; Kessler, H. J. Am. Chem. Soc. 2001, 123, 8189.
34. Ménand, M.; Blais, J.-C.; Valéry, J.-M.; Xie, J. J. Org. Chem. 2006, 71, 3295.
35. (a) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638.
36. (b) Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 1371.
37. (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.
38. (b) Coppola, C.; Saggiomo, V.; Di Fabio, G.; De Napoli, L.; Montesarchio, D. J. Org. Chem. 2007, 72, 9679.
39. García Fernández, J. M.; Ortiz Mellet, C.; Defaye, J. J. Inclusion Phenom. Macrocycl. Chem. 2006, 56, 149.
40. (a) García Fernández, J. M.; Jiménez Blanco, J. L.; Ortiz Mellet C.; Fuentes Mota, J. J. Chem. Soc., Chem. Commun. 1995, 57.
41. (b) Jiménez Blanco, J. L.; Benito, J. M; Ortiz Mellet C.; García Fernández, J. M. Org. Lett. 1999, 1, 1217.
42. (c) Benito, J. M; Jiménez Blanco, J. L.; Ortiz Mellet C.; García Fernández, J. M. Angew. Chem., Int. Ed. 2002, 41, 3674.
43. (a) Jiménez Blanco, J. L.; Bootello, P.; Ortiz Mellet, C.; Gutiérrez Gallego, R.; García Fernández, J. M. Chem. Commun. 2004, 92.
44. (b) Jiménez Blanco, J. L.; Bootello, P.; Ortiz Mellet, C.; García Fernández, J. M. Eur. J. Org. Chem. 2006, 183.
45. (c) Jiménez Blanco, J. L.; Bootello, P.; Gutiérrez Gallego, R.; Ortiz Mellet, C.; García Fernández, J. M. Synthesis 2007, 2545.
46. Jiménez Blanco, J. L.; Bootello, P.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2006, 71, 5136.
47. Jiménez Blanco, J. L.; García Fernández, J. M.; Gadelle, A.; Defaye, J. Carbohydr. Res. 1997, 303, 367.
48. 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.
49. (a) Ortiz Mellet, C.; Benito, J. M.; García Fernández, J. M.; Law, H.; Chmusrki, K.; Defaye, J.; O'Sullivan, M. L.; Caro, H. Chem. Eur. J. 1998, 4, 2523.
50. (b) Baussanne, I.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M.; Defaye, J. ChemBioChem 2001, 2, 777.
51. (c) Gómez-García, M.; Benito, J. M.; Rodríguez- Lucena, D.; Ortiz Mellet, C.; Yu, J.-X.; Chmurski, K.; Maestre, A.; Gutiérrez-Gallego, R.; Defaye, J.; García, Fernández, J. M. J. Am. Chem. Soc. 2005, 127, 7970.
52. (d) Reference 4d.
53. 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.
54. 6-Amino-6′-(tert-butoxycarbonylamino)-6,6′-dideoxy-2, 3,4,2′,3′,4′-hexa-O-trimethylsilyl-α, α′-trehalose was prepared in 18% overall yield from α,α′-trehalose over five steps.
55. Gobolobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437.
56. Meldal, M.; Juliano, M. A.; Jansson, A. M. Tetrahedron Lett. 1997, 38, 2531.
57. Bayley, H.; Standring, D. N.; Knowles, J. R. Tetrahedron Lett. 1978, 19, 3633.
58. 4 system in statistic reduction of azides; see: Katajisto, J.; Karskela, T.; Heinonen, P.; Lönnberg, H. J. Org. Chem. 2002, 67, 7995.
59. 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.
60. Anet, F. A.; Jochims, J. C.; Bradley, C. H. J. Am. Chem. Soc. 1970, 92, 2557.
61. (a) Molina, P.; Alajarín, M.; Sánchez-Andrada, P.; Elguero, J.; Jimeno, M. L. J. Org. Chem. 1994, 59, 7306.
62. (b) Molina, P.; Alajarín, M.; Sánchez-Andrada, P.; Carrió, J. S.; Martínez-Ripoll, M.; Anderson, E. J.; Jimeno, M. L.; Elguero, J. J. Org. Chem. 1996, 61, 4289.
63. Alajarin, M.; Molina, P.; Sanchez-Andrada, P.; Foces-Foces, C. J. Org. Chem. 1999, 64, 1121.
64. CCDC-3765 contains the supplementary crystallographic data for 9. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: (+44)1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).
65. (a) Kirschner, K. N.; Woods, R. J. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 10541.
66. (b) Bock, K.; Duus, J.; Jens, O. J. Carbohydr. Chem. 1994, 13, 513.
67. The formation of seven-membered NH⋯O intramolecular hydrogen bonds has already been found to be a dominant structural feature in sugar thioureas, being associated to the E,Z rotameric form. See ref 21b and: García Fernández, J. M.; Ortiz Mellet, C.; Jiménez Blanco, J. L.; Fuentes, J.; Diánez, M. J.; Estrada, M. D.; López-Castro, A.; Pérez Garrido, S. Carbohydr. Res. 1996, 286, 55.
68. (a) Ortiz Mellet, C.; Moreno Marín, A.; Jiménez Blanco, J. L.; García Fernández, J. M.; Fuentes, J. Tetrahedron: Asymmetry 1994, 5, 2325.
69. (b) Ortiz Mellet, C.; García Fernández, J. M. Sulfur Rep. 1996, 19, 61.
70. (c) Ortiz Mellet, C.; García Fernández, J. M. Adv. Carbohydr. Chem. Biochem. 2000, 55, 35.
71. 2+ pair. The absence of complexation in the case of 21 and 23 supports the involvement of the thiocarbonyl sulfur atoms in complex formation. The existence of inclusion phenomena is unlike, anyway, in view of the discussed conformational properties.
72. The 1:1 complex stoichiometry was confirmed by the continious variation method (Job plot). For a thorough description, see: Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley: Chichester, U.K., 1987.
73. (b) Job, P. Ann. Chim. 1928, 9, 113.
74. For a complete survey on complexation thermodynamics of CDs, see: Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
75. As a matter of fact, compound 26 behaved as a very efficient AC scavenger in competitive experiments with βCD derivatives, which has been exploited in the design of molecular switchers. See ref 8b.
76. Turner, D. C.; Brand, L. Biochemistry 1968, 7, 3381.
77. 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%. Binding isotherms were fitted using the MicroMath Scientist Software.