Construction of α-helix peptides with β-cyclodextrin and dansyl units and their conformational and molecular sensing properties

Chemistry - A European Journal

Volumn 6, Issue 10, 2000, Pages 1781-1788

  Matsumura, Sachiko ^a   Sakamoto, Seiji ^a   Ueno, Akihiko ^a   Mihara, Hisakazu ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Cyclodextrins; Helical structures; Inclusion compounds; Molecular recognition; Peptides

Indexed keywords

BETA CYCLODEXTRIN; CYCLODEXTRIN; DANSYL CHLORIDE; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; COMPLEX FORMATION; FLUORESCENCE; MOLECULAR GENETICS; MOLECULAR INTERACTION; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; PROTEIN TERTIARY STRUCTURE; SPECTROSCOPY;

AMINO ACID SEQUENCE; BETA-CYCLODEXTRINS; CYCLODEXTRINS; DANSYL COMPOUNDS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN CONFORMATION; SPECTRUM ANALYSIS;

EID: 0034660248     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000515)6:10<1781::aid-chem1781>3.3.co;2-q     Document Type: Article

References (62)

1. Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996.
2. a) J. W. Bryson, S. F. Betz, H. S. Lu, D. J. Suich, H. X. Zhou, K. T. O'Neill, W. F. DeGrado, Science 1995, 270, 935-941;
3. b) S. F. Betz, J. W. Bryson, W. F. DeGrado, Curr. Opin. Struct. Biol. 1995, 5, 457-463.
4. a) L. Brive, G. T. Dolphin, L. Baltzer, J. Am. Chem. Soc. 1997, 119, 8598-8607;
5. b) L. Baltzer, Curr. Opin. Struct. Biol. 1998, 8, 466-470;
6. c) L. Baltzer, K. S. Broo, Biopolymers 1998, 47, 31-40.
7. a) G. K. Walkup, B. Imperiali, J. Am. Chem. Soc. 1997, 119, 3443-3450;
8. b) M. D. Struthers, R. P. Cheng, B. Imperiali, Science 1996, 271, 342-345.
9. a) M. Engels, D. Bashford, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 9151-9158;
10. b) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature (London) 1994, 369, 301-304.
11. J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187.
12. a) Comprehensive Supramolecular Chemistry, Vol. 3 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J. Szejtli, T. Osa), Pergamon, Oxford, 1996;
13. b) R. Breslow, S. D. Dong, Chem. Rev. 1998,. 98, 1997-2011;
14. c) A. R. Hedges, Chem. Rev. 1998, 98, 2035-2044;
15. d) M. L. Bender, M. Komiyama, Cyclodextrin Chemistry, Springer, Berlin, 1978.
16. A. Ueno in Fluorescent Chemosensors for Ion and Molecule Recognition (Ed.: A. W. Czarnick), ACS Symposium Series 538, American Chemical Society, Washington, DC, 1993, pp. 74-84.
17. a) A. Ueno, T. Kuwabara, A. Nakamura, F. Toda, Nature (London) 1992, 356, 136-137;
18. b) T. Aoyagi, A. Nakamura, H. Ikeda, T. Ikeda, H. Mihara, A. Ueno, Anal. Chem. 1997, 69, 659-663;
19. c) K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki, T. Osa, J. Am. Chem. Soc. 1993, 115, 5035-5040.
20. a) A. Ueno, A. Ikeda, H. Ikeda, T. Ikeda, F. Toda, J. Org. Chem. 1999, 64, 382-387;
21. b) M. Nakamura, A. Ikeda, N. Ise, T. Ikeda, H. Ikeda, F. Toda, A. Ueno, J. Chem. Soc. Chem. Commun. 1995, 721-722;
22. c) H. Ikeda, M. Nakamura, N. Ise, N. Oguma, A. Nakamura, T. Ikeda, F. Toda, A. Ueno, J. Am. Chem. Soc. 1996, 118, 10980-10988;
23. d) Y. Wang, T. Ikeda, H. Ikeda, A. Ueno, F. Toda, Bull. Chem. Soc. Jpn. 1994, 67, 1598-1607.
24. a) R. Breslow, B. Zhang, J. Am. Chem. Soc. 1996, 118, 8495-8496;
25. b) R. Breslow, S. Chung, J. Am. Chem. Soc. 1990, 112, 9659-9660;
26. c) R. Breslow, N. Greenspoon, T. Guo, R. Zarzycki, J. Am. Chem. Soc. 1989, 111, 8296-8297.
27. a) W. D. Kohn, C. M. Kay, B. D. Sykes, R. S. Hodges, J. Am. Chem. Soc. 1998, 120, 1124-1132;
28. b) N. E. Zhou, C. M. Kay, B. D. Sykes, R. S. Hodges, Biochemistry 1993, 32, 6190-6197.
29. a) K. R. Shoemaker, P. S. Kim, E. J. York, J. M. Stewart, R. L. Baldwin, Nature (London) 1987, 326, 563-567;
30. b) K. R. Shoemaker, P. S. Kim, D. N. Brems, S. Marqusee, E. J. York, I. M. Chaiken, J. M. Stewart, R. L. Baldwin, Proc. Natl. Acad. Sci. USA 1985, 82, 2349-2353;
31. c) P. B. Harbury, T. Zhang, P. S. Kim, R. L. Baldwin, Science 1993, 262, 1401-1407;
32. d) G. Merutka, W. Shalongo, E. Stellwagen, Biochemistry 1991, 30, 4245-4248.
33. a) M. Allert, M. Kjellatrand, K. Broo, Å. Nilsson, L. Baltzer, Chem. Commun. 1998, 1547-1548;
34. b) K. S. Broo, H. Nilsson, J. Nilsson, L. Baltzer, J. Am. Chem. Soc. 1998, 120, 10287-10295.
35. a) R. B. Hill, W. F. DeGrado, J. Am. Chem. Soc. 1998, 120, 1138-1145;
36. b) S. T. R. Walsh, H. Cheng, J. W. Bryson, H. Roder, W. F. DeGrado, Proc. Natl. Acad. Sci. USA 1999, 96, 5486-5491.
37. R. Corradini, A. Dossena, R. Marchelli, A. Panagia, G. Sartor, M. Saviano, A. Lombardi, V. Pavone, Chem. Eur. J. 1996, 2, 373-381.
38. R. A. Dunbar, F. V. Bright, Supramol. Chem. 1994, 3, 93-99.
39. S. Marqusee, R. L. Baldwin, Proc. Natl. Acad. Sci. USA 1987, 84, 8898-8902.
40. S.-H. Park, W. Shalongo, E. Stellwagen, Biochemistry 1993, 32, 12901-12905.
41. T. Morii, J. Yamane, Y. Aizawa, K. Makino, Y. Sugiura, J. Am. Chem. Soc. 1996, 118, 10011-10017.
42. a) N. Kobayashi, S. Minato, T. Osa, Macromol. Chem. 1983, 184, 2123-2132;
43. b) N. Kobayashi, R. Saito, H. Hino, Y. Hino, A. Ueno, T. Osa, J. Chem. Soc. Perkin. Trans. 2, 1983, 1031-1035.
44. a) K. Harata, H. Uedaira, Bull. Chem. Soc. Jpn. 1975, 48, 375-378:
45. b) K. Harata, Bull. Chem. Soc. Jpn. 1978, 51, 2737-2738;
46. c) H. Shimizu, A. Kaito, M. Hatano, Bull. Chem. Soc. Jpn. 1979, 52, 2678-2684.
47. a) M. Kodaka, J. Phys. Chem. 1991, 95, 2110-2112;
48. b) M. Kodaka, J. Am. Chem. Soc. 1993, 115, 3702-3705.
49. a) M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, R. Chûjô, Bull. Chem. Soc. Jpn. 1988, 61, 4225-4229;
50. b) M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue, R. Chûjô, Carbohydr. Res. 1990, 198, 181-191;
51. c) A. Botsi, K. Yannakopoulou, E. Hadjoudis, J. Waite, Carbohydr. Res. 1996, 283, 1-16.
52. a) R. F. Chen, Arch. Biochem. Biophys. 1967, 120, 609-620;
53. b) J. B. Bridge, P. Johnson, Eur. Polym. J. 1973, 9, 1327-1346.
54. F. V. Bright, G. C. Catena, J. Huang, J. Am. Chem. Soc. 1990, 112, 1343-1346.
55. a) R. Wang, F. V. Bright, Appl. Spectrosc. 1993, 46, 792-799;
56. b) R. Wang, F. V. Bright, Appl. Spectrosc. 1993, 46, 800-806.
57. a) B. R. Gibney, F. Rabanal, J. J. Skalicky, A. J. Wand, P. L. Datton, J. Am. Chem. Soc. 1999, 121, 4952-4960;
58. b) J. K. Myers, C. N. Pace, J. M. Scholtz, Protein Sci. 1995, 4, 2138-2148.
59. E. Atherton, R. C. Sheppard, Solid Phase Peptide Synthesis: A Practical Approach, IRL Press, Oxford, 1989.
60. H. Rink, Tetrahedron Lett. 1987, 28, 3787-3790.
61. E. Kaiser, R. L. Colescott, C. D. Bossinger, Anal. Biochem. 1970, 34, 595-598.
62. N. Fujii, A. Otaka, O. Ikemura, K. Akagi, S. Funakoshi, Y. Hayashi, Y. Kuroda, H. Yajima, J. Chem. Soc. Chem. Commun. 1987, 274-275.