Controlled stability of the triple-stranded helical structure of a β-1,3-glucan with a chromophoric aromatic moiety at a peripheral position

Chemistry - An Asian Journal

Volumn 2, Issue 10, 2007, Pages 1290-1298

  Ikeda, Masato ^a,b   Haraguchi, Shuichi ^a   Numata, Munenori ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Helical structures; Metal ligand interactions; Polysaccharides; Self assembly; Structural transitions

Indexed keywords

BETA 1,3 GLUCAN; BETA GLUCAN; BETA-1,3-GLUCAN; CURDLAN; DIMETHYL SULFOXIDE; ION; UNCLASSIFIED DRUG; ZINC;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

BETA-GLUCANS; CIRCULAR DICHROISM; DIMETHYL SULFOXIDE; IONS; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR CONFORMATION; SPECTROPHOTOMETRY, ULTRAVIOLET; ZINC;

EID: 35048867915     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700150     Document Type: Article

References (74)

1. a) J. D. Watson, F. H. C. Crick, Nature 1953, 171, 737-738;
2. b) A. Rich, D. R. Davies, F. H. C. Crick, J. D. Watson. J. Mol. Biol. 1961, 3, 71-86.
3. a) J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995;
4. b) C. Piguet, G. Bernardinelli, G. Hopfgartner, Chem. Rev. 1997, 97, 2005-2062;
5. c) M. Albrecht. Chem. Rev. 2001, 101, 3457-3497.
6. a) V. Berl, I. Hue, R. G. Khoury, M. J. Krische, J.-M. Lehn, Nature 2000, 407, 720-723;
7. b) I. Hue, Eur. J. Org. Chem. 2004, 17-29;
8. c) Y. Tanaka, H. Katagiri, Y. Furusho, E. Yashima, Angew. Chem. 2005, 117, 3935-3938;
9. Angew. Chem. Int. Ed. 2005, 44, 3867-3870;
10. d) Y. Furusho, Y. Tanaka, E. Yashima, Org. Lett. 2006, 8, 2583-2586;
11. e) M. Ikeda, Y. Tanaka, T. Hasegawa, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2006, 128, 6806-6807;
12. f) T. Sugimoto, T. Suzuki, S. Shinkai, K. Sada, J. Am. Chem. Soc. 2007, 129, 270-271.
13. a) H. Kusanagi, Polym. J. 1996, 28, 708-711;
14. b) H. M. Janssen, E. Peeters, M. F. van Zundert, M. H. P. van Genderen, E. W. Meijer, Angew. Chem. 1997, 109, 152-154;
15. Angew. Chem. Im. Ed. Engl. 1997, 36, 122-125;
16. c) H. Goto, H. Katagiri, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2006, 128, 7176-7178.
17. For reviews on helical architecture, see: a) M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook. S. Lifson, Science 1995, 268, 1860-1866;
18. b) T. Nakano, Y. Okamoto, Chem. Rev. 2001, 101, 4013-4038;
19. c) J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 107, 4039-4070;
20. d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011;
21. e) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004, 10, 42-51;
22. f) Y. Furusho, E. Yashima, Chem. Rec. 2007, 7, 1-11.
23. a) R. Krämer, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. 1993, 105, 764-767;
24. Angew. Chem. Int. Ed. Engl. 1993, 32, 703-706;
25. b) A. F. Cotton, L. M. Daniels, G. T. Jordan, C. A. Murillo, J. Am. Chem. Soc. 1997, 179, 10377-10381;
26. c) Y.-H. Chen, C.-C. Lee, C.-C. Wang, G.-H. Lee, S.-Y. Lai, F.-Y. Li, C.-Y. Mou, S.-M. Peng. Chem. Commun. 1999, 1667-1668.
27. a) R. W. Saalfrank, N. Low, S. Trummer, G. M. Sheldrick, M. Teichert, D. Stalke, Eur. J. Inorg. Chem. 1998, 559-563;
28. b) M. Albrecht, K. Witt, H. Röttele, R. Fröhlich, Chem. Commun. 2001, 1330-1331.
29. a) T. Koide, M. Yuguchi, M. Kawakita, H. Konno, J. Am. Chem. Soc. 2002, 124, 9388-9389;
30. b) W. Cai, S. W. Kwok, J. P. Taulane, M. Goodman, J. Am. Chem. Soc. 2004, 126, 15030-15031;
31. c) U. Kusebauch, S. A. Cadamuro, H.-J. Musiol, M. O. Lenz, J. Wachtveitl, L. Moroder, C. Renner, Angew. Chem. 2006, 118, 7170-7173;
32. Angew. Chem. Int. Ed. 2006, 45, 7015-7018.
33. a) D. A. Rees, E. J. Welsh, Angew. Chem. 1977, 89, 228-239;
34. Angew. Chem. Int. Ed. Engl. 1977, 16, 214-224;
35. b) V. S. R. Rao, P. K. Qasba, P. V. Balaji, R. Chandrasekaran, Conformation of Carbohydrates, Harwood, Amsterdam, 1998.
36. a) B. K. Sathyanarayana, V. S. R. Rao, Biopolymers 1971, 10, 1605-1615;
37. b) Y. Deslandes, R. H. Marchessault, A. Sarko, Macromolecules 1980, 13, 1466-1471;
38. c) T. Norisuye, K. Yanaki, H. Fujita, Macromolecules 1980, 13, 1462-1466.
39. K. Sakurai, K. Uezu, M. Numata, T. Hasegawa, C. Li, K. Kaneko, S. Shinkai, Chem. Commun. 2005, 4383-4398, and references cited therein.
40. a) K. Sakurai, S. Shinkai, J. Am. Chem. Soc. 2000, 122, 4520-4521;
41. b) K. Sakurai, M. Mizu, S. Shinkai, Biomacromolecules 2001, 2, 641-650;
42. c) A.-H. Bae, S.-W. Lee, M. Ikeda, M. Sano, S. Shinkai, K. Sakurai, Carbohydr. Res. 2004, 339, 251-258;
43. d) K. Miyoshi, K. Uezu, K. Sakurai, S. Shinkai, Biomacromolecules 2005, 6, 1540-1546.
44. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless. Angew. Chem. 2002, 114, 2708-2711;
45. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
46. a) T. Hasegawa, M. Umeda, M. Numata, C. Li, A.-H. Bae, T. Fujisawa, S. Haraguchi, K. Sakurai, S. Shinkai, Chem. Lett. 2006, 35, 82-83;
47. b) T. Hasegawa, M. Umeda, M. Numata, C. Li, A.-H. Bae, T. Fujisawa, S. Haraguchi, K. Sakurai, S. Shinkai, Carbohydr. Res. 2006, 341, 35-40.
48. a) M. Ikeda, T. Hasegawa, M. Numata, K. Sugikawa, K. Sakurai, M. Fujiki, S. Shinkai, J. Am. Chem. Soc. 2007, 129, 3979-3988.
49. a) P. A. J. de Witte, M. Castriciano, J. J. L. M. Cornelissen, L. M. Scolaro, R. J. M. Nolte, A. E. Rowan, Chem. Eur. J. 2003, 9, 1775-1781;
50. b) P. A. J. de Witte, J. Hernando, E. E. Neuteboom, E. M. H. P. van Dijk, S. C. J. Meskers, R. A. J. Janssen, N. F. van Hulst, J. M. R. Nolte, M. F. García-Parajó, A. E. Rowan, J. Phys. Chem. B 2006, 110, 7803-7812;
51. c) M. F. García-Parajó, J. Hernando, G. S. Mosteiro, J. P. Hoogenboom, E. M. H. P. van Dijk, N. F. van Hulst, ChemPhysChem 2005, 6, 819-827.
52. a) T. Sato, T. Norisuye, H. Fujita, Carbohydr. Res. 1981, 95, 195-204;
53. b) T. Sato, T. Norisuye, H. Fujita, Macromolecules 1983, 16, 185-189;
54. c) S. Kitamura, T. Kuge, Biopolymers 1989, 28, 639-654;
55. d) T. M. McIntire, D. A. Brant, J. Am. Chem. Soc. 1998, 120, 6909-6919.
56. S.-i. Sakurai, K. Kuroyanagi, R. Nonokawa, E. Yashima, J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 5838-5844.
57. a) M. Barboiu, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2002, 99, 5201-5206;
58. b) C. Dolain, V. Maurizot, I. Huc, Angew. Chem. 2003, 115, 2844-2846;
59. Angew. Chem. Int. Ed. 2003, 42, 2738-2740;
60. c) E. Kolomiets, V. Berl, I. Odriozola, A.-M. Stadler, N. Kyritsakas, J.-M. Lehn, Chem. Commun. 2003, 2868-2869;
61. d) H. Abe, N. Masuda, M. Waki, M. Inouye, J. Am. Chem. Soc. 2005, 127, 16189-16196.
62. a) V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J.-M. Lehn, Chem. Eur. J. 2001, 7, 2810-2820;
63. b) H. Goto, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2007, 129, 109-112.
64. a) H. Goto, E. Yashima, J. Am. Chem. Soc. 2002, 124, 7943-7949;
65. b) H. Miyake, K. Yoshida, H. Sugimoto, H. Tsukube, J. Am. Chem. Soc. 2004, 126, 6524-6525;
66. c) T. Tanaka, T. Mizuno, S. Fukui, H. Hiroaki, J. Oku, K. Kanaori, K. Tajima, M. Shirakawa, J. Am. Chem. Soc. 2004, 126, 14023-14028.
67. a) L. G. Purnell, J. C. Shepherd, D. J. Hodgson, J. Am. Chem. Soc. 1975, 97, 2376-2380;
68. b) S. Komeda, M. Lutz, A. L. Spek, Y. Yamanaka, T. Sato, M. Chikuma, J. Reedijk, J. Am. Chem. Soc. 2002, 124, 4738-4746;
69. c) T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853-2855;
70. d) R. Bronisz, Inorg. Chem. 2005, 44, 4463-4465.
71. a) R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271;
72. b) S. Yano, Y. Mikata, Bull. Chem. Soc. Jpn. 2002, 75, 2097-2113.
73. S. J. Paisey, P. J. Sadler, Chem. Commun. 2004, 306-307.
74. W. D. Oosterbaan, P. C. M. van Gerven, C. A. van Walree, M. Koeberg, J. J. Piet, R. W. A. Havenith, J. W. Zwikker, L. W. Jenneskens, R. Gleiter, Eur. J. Org. Chem. 2003, 3117-3130.