Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3366-3371

  Abe, Hajime ^a   Chida, Yusuke ^a   Kurokawa, Hiroyuki ^a   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING STRENGTH; CDS; HOST MOLECULES; MACROCYCLES; MACROCYCLICS; OXIDATIVE HOMOCOUPLING; PYRIDONES; SACCHARIDE RECOGNITION; SELECTIVE BINDING;

ACETYLENE; BIOCATALYSTS; SUGARS;

PYRIDINE;

ACETYLENE; ALKANE DERIVATIVE; CARBOHYDRATE; CUPRIC ION; DIETHYNYL; DIPYRONE; DISACCHARIDE; DODECYL BETA MALTOSIDE; HEXOSE; MACROCYCLIC COMPOUND; MALTOSE; MALTOSIDE; OCTYL MONOHEXOSIDE; PYRIDINE; UNCLASSIFIED DRUG; DODECYL MALTOSIDE; GLUCOSIDE; PYRIDONE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS COUPLING REACTION; CROSS LINKING; MOLECULAR RECOGNITION; MOLECULE; OXIDATION; STEREOCHEMISTRY; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY;

ACETYLENE; GLUCOSIDES; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRIDONES; SUBSTRATE SPECIFICITY;

EID: 79955551690     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2003055     Document Type: Article

References (84)

1. Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, 1991.
2. Crown Compounds; Cooper, S. R., Ed.; VCH: New York, 1992.
3. Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001.
4. For recent reviews for saccharide recognition by synthetic host molecules, see: Penadés, S., Ed. Host-Guest Chemistry - Mimetic Approaches to Study Carbohydrate Recognition. Topics in Current Chemistry Springer-Verlag: Berlin, 2002; Vol. 218.
5. Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978-2996
6. Walker, D. B.; Joshi, G.; Davis, A. P. Cell. Mol. Life Sci. 2009, 66, 3177-3191
7. Mazik, M. Chem. Soc. Rev. 2009, 38, 935-956
8. Kubik, S. Angew. Chem., Int. Ed. 2009, 48, 1722-1725
9. Carroll, C. N.; Naleway, J. J.; Haley, M. M.; Johnson, D. W. Chem. Soc. Rev. 2010, 39, 3875-3888
10. For recent examples of macrocyclic host molecules for saccharide recognition, see: Barwell, N. P.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2009, 48, 7673-7676
11. Ferrand, Y.; Klein, E.; Barwell, N. P.; Crump, M. P.; Jiménez-Barbero, J.; Vicent, C.; Boons, G.-J.; Ingale, S.; Davis, A. P. Angew. Chem., Int. Ed. 2009, 48, 1775-1779
12. Ferrand, Y.; Crump, M. P.; Davis, A. P. Science 2007, 318, 619-622
13. Klein, E.; Ferrand, Y.; Auty, E. K.; Davis, A. P. Chem. Commun. 2007, 2390-2392
14. Klein, E.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2005, 44, 298-302
15. Velasco, T.; Lecollinet, G.; Ryan, T.; Davis, A. P. Org. Biomol. Chem. 2004, 2, 645-647
16. Lecollinet, G.; Dominey, A. P.; Velasco, T.; Davis, A. P. Angew. Chem., Int. Ed. 2002, 41, 4093-4096
17. Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866
18. Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1998, 37, 2270-2273
19. Ardá, A.; Venturi, C.; Nativi, C.; Francesconi, O.; Gabrielli, G.; Cañada, F. J.; Jiménez-Barbero, J.; Roelens, S. Chem. - Eur. J. 2010, 16, 414-418
20. Ardá, A.; Venturi, C.; Nativi, C.; Francesconi, O.; Cañada, F. J.; Jiménez-Barbero, J.; Roelens, S. Eur. J. Org. Chem. 2010, 64-71
21. Nativi, C.; Cacciarini, M.; Francesconi, O.; Vacca, A.; Moneti, G.; Ienco, A.; Roelens, S. J. Am. Chem. Soc. 2007, 129, 4377-4385
22. Francesconi, O.; Ienco, A.; Moneti, G.; Native, C.; Roelens, S. Angew. Chem., Int. Ed. 2006, 45, 6693-6696
23. Rauschenberg, M.; Bomke, S.; Karst, U.; Ravoo, B. J. Angew. Chem., Int. Ed. 2010, 49, 7340-7345
24. De Ryckea, N.; Marrota, J.; Coutya, F.; David, O. R.P. Tetrahedron Lett. 2010, 51, 6521-6525
25. Rusin, O.; Lang, K.; Král, V. Chem. - Eur. J. 2002, 8, 655-663
26. Rusin, O.; Lang, K.; Král, V. Org. Lett. 2001, 3, 873-876
27. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596
28. Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. Am. Chem. Soc. 1989, 111, 5397-5404
29. For recent examples of acyclic host molecules for saccharide recognition by hydrogen bonding, see: Mazik, M.; Sonnenberg, C. J. Org. Chem. 2010, 75, 6416-6423
30. Mazik, M.; Hartmann, A.; Jones, P. G. Chem. - Eur. J. 2009, 15, 9147-9159
31. Mazik, M.; Buthe, A. C. Org. Biomol. Chem. 2009, 7, 2063-2071
32. Mazik, M.; Buthe, A. C. Org. Biomol. Chem. 2008, 6, 1558-1568
33. Mazik, M.; Kuschel, M. Chem. - Eur. J. 2008, 14, 2405-2419
34. Mazik, M.; Buthe, A. C. J. Org. Chem. 2007, 72, 8319-8326
35. Mazik, M.; Kuschel, M.; Sicking, W. Org. Lett. 2006, 8, 855-858
36. Mazik, M.; Cavga, H. J. Org. Chem. 2006, 71, 2957-2963
37. Mazik, M.; Cavga, H.; Jones, P. G. J. Am. Chem. Soc. 2005, 127, 9045-9052
38. Mazik, M.; Sicking, W. Tetrahedron Lett. 2004, 45, 3117-3121
39. Mazik, M.; Radunz, W.; Boese, R. J. Org. Chem. 2004, 69, 7448-7462
40. Kalenius, E.; Koivukorpi, J.; Kolehmainen, E.; Vainiotalo1, P. Eur. J. Org. Chem. 2010, 1052-1058
41. Lee, J.-D.; Kim, Y.-H.; Hong, J.-I. J. Org. Chem. 2010, 75, 7588-7595
42. Striegler, S.; Gichinga, M. G. Chem. Commun. 2008, 5930-5932
43. Palde, P. B.; Gareiss, P. C.; Miller, B. L. J. Am. Chem. Soc. 2008, 130, 9566-9573
44. He, C.; Lin, Z.; He, Z.; Duan, C.; Xu, C.; Wang, Z.; Yan, C. Angew. Chem., Int. Ed. 2008, 47, 877-881
45. Goto, H.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 7176-7178
46. Lu, W.; Zhang, L.-H.; Ye, X.-S.; Su, J.; Yu, Z. Tetrahedron 2005, 62, 1806-1816
47. ten Cate, M. G. J.; Reinhoudt, D. N.; Crego-Calama, M. J. Org. Chem. 2005, 70, 8443-8453
48. Lee, J.-D.; Greene, N. T.; Rushton, G. T.; Shimizu, K. D.; Hong, J.-I. Org. Lett. 2005, 7, 963-966
49. Fang, J.-M.; Selvi, S.; Liao, J.-H.; Slanina, Z.; Chen, C.-T.; Chou, P.-T. J. Am. Chem. Soc. 2004, 126, 3559-3566
50. Hou, J.-L.; Shao, X.-B.; Chen, G.-J.; Zhou, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2004, 126, 12386-12394
51. Ishi-i, T.; Mateos-Timoneda, M. A.; Timmerman, P.; Crego-Calama, M.; Reinhoudt, D. N.; Shinkai, S. Angew. Chem., Int. Ed. 2003, 42, 2300-2305
52. Tamaru, S.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4972-4976
53. Segura, M.; Bricoli, B.; Casnati, A.; Muñoz, E. M.; Sansone, F.; Ungaro, R.; Vicent, C. J. Org. Chem. 2003, 68, 6296-6303
54. Wada, K.; Mizutani, T.; Kitagawa, S. J. Org. Chem. 2003, 68, 5123-5131
55. Ladomenou, K.; Bonar-Law, R. P. Chem. Commun. 2002, 2108-2109
56. Kim, Y.-H.; Hong, J.-I. Angew. Chem., Int. Ed. 2002, 41, 2947-2950
57. Inouye, M.; Waki, M.; Abe, H. J. Am. Chem. Soc. 2004, 126, 2022-2027
58. Abe, H.; Masuda, N.; Waki, M.; Inouye, M. J. Am. Chem. Soc. 2005, 127, 16189-16196
59. Waki, M.; Abe, H.; Inouye, M. Chem. - Eur. J. 2006, 12, 7839-7847
60. Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059-3061
61. Abe, H.; Murayama, D.; Kayamori, F.; Inouye, M. Macromolecules 2008, 41, 6903-6909
62. Abe, H.; Takashima, S.; Yamamoto, T.; Inouye, M. Chem. Commun. 2009, 2121-2123
63. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425
64. Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341-345
65. Inouye, M.; Chiba, J.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176
66. Abe, H.; Machiguchi, H.; Matsumoto, S.; Inouye, M. J. Org. Chem. 2008, 73, 4650-4661
67. For recent examples of syntheses of ethynylpyridine-containing macrocyclic π-systems, see: Miki, K.; Fujita, M.; Inoue, Y.; Senda, Y.; Kowada, T.; Ohe, K. J. Org. Chem. 2010, 75, 3537-3540
68. Sonoda, M.; Yamaguchi, Y.; Tahara, K.; Hirose, K.; Tobe, Y. Tetrahedron 2008, 64, 11490-11494
69. Tobe, Y.; Nagano, A.; Kawabata, K.; Sonoda, M.; Naemura, K. Org. Lett. 2000, 2, 3265-3268
70. Opris, D. M.; Ossenbach, A.; Lentz, D.; Schlüter, A. D. Org. Lett. 2008, 10, 2091-2093
71. Grave, C.; Lentz, D.; Schäfer, A.; Samorì, P.; Rabe, J. P.; Franke, P.; Schlüter, A. D. J. Am. Chem. Soc. 2003, 125, 6907-6918
72. Spitler, E. L.; McClintock, S. P.; Haley, M. M. J. Org. Chem. 2007, 72, 6692-6699
73. Baxter, P. N. W.; Dali-Youcef, R. J. Org. Chem. 2005, 70, 4935-4953
74. Baxter, P. N. W. Chem. - Eur. J. 2003, 9, 5011-5022
75. Campbell, K.; Kuehl, C. J.; Ferguson, M. J.; Stang, P. J.; Tykwinski, R. R. J. Am. Chem. Soc. 2002, 124, 7266-7267
76. Campbell, K.; McDonald, R.; Tykwinski, R. R. J. Org. Chem. 2002, 67, 1133-1140
77. Yamaguchi, Y.; Yoshida, Z. Chem. - Eur. J. 2003, 9, 5430-5440
78. Kobayashi, S.; Yamaguchi, Y.; Wakamiya, T.; Matsubara, Y.; Sugimoto, K.; Yoshida, Z. Tetrahedron Lett. 2003, 44, 1469-1472
79. Jester, S.-S.; Shabelina, N.; Le Blanc, S. M.; Höger, S. Angew. Chem., Int. Ed. 2010, 49, 6101-6105
80. Shabelina, N.; Klyatskaya, S.; Enkelmann, V.; Höger, S. C. R. Chim. 2009, 12, 430-436
81. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657
82. Abe, H.; Kurokawa, H.; Chida, Y.; Inouye, M. J. Org. Chem. 2011, 76, 309-311
83. For selective polycyclic receptors for disaccharide recognition by Davis' group, see refs 2c,3d,g. See also refs 3n,4c-4f,4n for disaccharide-selective host molecules.
84. -1, respectively, by DFT (B3LYP/6-31+G(d)) calculations. See Figure S2, Supporting Information.