Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage

European Journal of Organic Chemistry

Volumn , Issue 9, 2013, Pages 1677-1682

  Kayamori, Fumihiro ^a   Abe, Hajime ^a   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Circular dichroism; Helical structures; Hydrogen bonds; Nitrogen heterocycles; Salt effect

Indexed keywords

EID: 84875023832     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201201376     Document Type: Article

References (56)

1. D. B. Amabilino (Ed.), Chirality at the Nanoscale, Wiley-VCH, Weinheim, Germany, 2009.
2. W. Saenger (Ed.), Principles of Nucleic Acid Structure, Springer-Verlag, New York, 1984.
3. T. E. Creighton (Ed.), Proteins: Structures and Molecular Principles, 2 ed., Freeman, New York, 1993.
4. C. Branden, C. Tooze (Eds.), Introduction to Protein Structure, Garland, New York, 1991.
5. J. Becerril, J. M. Rodriguez, I. Saraogi, A. D. Hamilton, in: Foldamers (Eds.:, S. Hecht, I. Huc), Wiley-VCH, Weinheim, Germany, 2007, pp. 195-228.
6. B.-B. Ni, Q. Yan, Y. Ma, D. Zhao, Coord. Chem. Rev. 2010, 254, 954-971.
7. H. Juwarker, J. Suk, K.-S. Jeong, Chem. Soc. Rev. 2009, 38, 3316-3325.
8. Z.-T. Li, J.-L. Hou, C. Li, Acc. Chem. Res. 2008, 41, 1343-1353.
9. R. A. Smaldone, J. S. Moore, Chem. Eur. J. 2008, 14, 2650-2657.
10. Z.-T. Li, J.-L. Hou, C. Li, H.-P. Yi, Chem. Asian J. 2006, 1, 766-778.
11. C. R. Ray, J. S. Moore, Adv. Polym. Sci. 2005, 177, 91-149.
12. For recent reviews of chiral helical foldamers, see
13. E. Yashima, K. Maeda, in: Foldamers (Eds.:, S. Hecht, I. Huc), Wiley-VCH, Weinheim, Germany, 2007, pp. 331-366.
14. [1]
15. E. Yashima, K. Maeda, H. Iida, Y. Furusho, K. Nagai, Chem. Rev. 2009, 109, 6102-6211.
16. I. Saraogi, A. D. Hamilton, Chem. Soc. Rev. 2009, 38, 1726-1743.
17. E. Yashima, K. Maeda, Y. Furusho, Acc. Chem. Res. 2008, 41, 1166-1180.
18. E. Yashima, K. Maeda, Macromolecules 2008, 41, 3-12.
19. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011.
20. R. A. Brown, T. Marcelli, M. De Poli, J. Solà, J. Clayden, Angew. Chem. 2012, 124, 1424-1428; Angew. Chem. Int. Ed. 2012, 51, 1395 -1399.
21. H. Ito, M. Ikeda, T. Hasegawa, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2011, 133, 3419-3432.
22. A. M. Kendhale, L. Poniman, Z. Dong, K. Laxmi-Reddy, B. Kauffmann, Y. Ferrand, I. Huc, J. Org. Chem. 2011, 76, 195-200.
23. T. Buffeteau, L. Ducasse, L. Poniman, N. Delsuc, I. Huc, Chem. Commun. 2006, 2714-2716.
24. V. Maurizot, C. Dolain, I. Huc, Eur. J. Org. Chem. 2005, 1293-1301.
25. C. Dolain, H. Jiang, J.-M. Léger, P. Guionneau, I. Huc, J. Am. Chem. Soc. 2005, 127, 12943-12951.
26. C. Dolain, V. Maurizot, I. Huc, Angew. Chem. 2003, 115, 2844-2846; Angew. Chem. Int. Ed. 2003, 42, 2738 -2740.
27. H.-Y. Hu, J.-F. Xiang, Y. Yang, C.-F. Chen, Org. Lett. 2008, 10, 1275-1278.
28. E. D. King, P. Tao, T. T. Sanan, C. M. Hadad, J. R. Parquette, Org. Lett. 2008, 10, 1671-1674.
29. G. Y. Nath, S. Samal, S.-Y. Park, C. N. Murthy, J.-S. Lee, Macromolecules 2006, 39, 5965-5966.
30. D. Pijper, B. L. Feringa, Angew. Chem. 2007, 119, 3767-3770; Angew. Chem. Int. Ed. 2007, 46, 3693 -3696.
31. H. Abe, D. Murayama, F. Kayamori, M. Inouye, Macromolecules 2008, 41, 6903-6909.
32. H. Abe, H. Makida, M. Inouye, Heterocycles 2012, 86, 955-963.
33. H. Abe, H. Makida, M. Inouye, Tetrahedron 2012, 68, 4353-4361.
34. H. Abe, Y. Ohishi, M. Inouye, J. Org. Chem. 2012, 77, 5209-5214.
35. H. Abe, K. Okada, H. Makida, M. Inouye, Org. Bioorg. Chem. 2012, 10, 6930-6936.
36. S. Takashima, H. Abe, M. Inouye, Chem. Commun. 2012, 48, 3330-3332.
37. S. Takashima, H. Abe, M. Inouye, Chem. Commun. 2011, 47, 7455-7457.
38. H. Abe, S. Takashima, T. Yamamoto, M. Inouye, Chem. Commun. 2009, 2121-2123.
39. H. Abe, H. Machiguchi, S. Matsumoto, M. Inouye, J. Org. Chem. 2008, 73, 4650-4661.
40. M. Waki, H. Abe, M. Inouye, Angew. Chem. 2007, 119, 3119-3121; Angew. Chem. Int. Ed. 2007, 46, 3059 -3061.
41. M. Waki, H. Abe, M. Inouye, Chem. Eur. J. 2006, 12, 7839-7847.
42. H. Abe, N. Masuda, M. Waki, M. Inouye, J. Am. Chem. Soc. 2005, 127, 16189-16196.
43. M. Inouye, M. Waki, H. Abe, J. Am. Chem. Soc. 2004, 126, 2022-2027.
44. For recent reviews regarding association between synthetic host molecules and saccharide guests, see
45. X. Yang, Y. Cheng, B. Wang, in: Carbohydrate Recognition: Biological Problems, Methods, and Applications (Eds.:, B. Wang, G.-J. Boons), Wiley, Hoboken, 2011, pp. 301-327.
46. S. Penadés (Ed.), Host-Guest Chemistry-Mimetic Approaches to Study Carbohydrate Recognition Top. Curr. Chem., vol. 218, Springer-Verlag, Berlin, 2002.
47. M. Mazik, RSC Adv. 2012, 2, 2630-2642.
48. C. N. Carroll, J. J. Naleway, M. M. Haley, D. W. Johnson, Chem. Soc. Rev. 2010, 39, 3875-3888.
49. S. Jin, Y. Cheng, S. Reid, M. Li, B. Wang, Med. Res. Rev. 2010, 30, 171-257.
50. M. Mazik, Chem. Soc. Rev. 2009, 38, 935-956.
51. A. P. Davis, Org. Bioorg. Chem. 2009, 7, 3629-3638.
52. D. B. Walker, G. Joshi, A. P. Davis, Cell. Mol. Life Sci. 2009, 66, 3177-3191.
53. A. P. Davis, R. S. Wareham, Angew. Chem. 1999, 111, 3160-3179; Angew. Chem. Int. Ed. 1999, 38, 2978 -2996.
54. K. J. Edgar, S. N. Falling, J. Org. Chem. 1990, 55, 5287-5291.
55. M. Inouye, J. Chiba, H. Nakazumi, J. Org. Chem. 1999, 64, 8170-8176.
56. P.-Y. Michellys, R. J. Ardecky, J.-H. Chen, J. D'Arrigo, T. A. Grese, D. S. Karanewsky, M. D. Leibowitz, S. Liu, D. A. Mais, C. M. Mapes, C. Montrose-Rafizadeh, K. M. Ogilvie, A. Reifel-Miller, D. Rungta, A. W. Thompson, J. S. Tyhonas, M. F. J. Boehm, J. Med. Chem. 2003, 46, 4087-4103.