Tuning the cavity of cyclodextrins: Altered sugar adaptors in protein pores

Journal of the American Chemical Society

Volumn 133, Issue 6, 2011, Pages 1987-2001

  Li, Wen Wu ^a   Claridge, Timothy D W ^a   Li, Qiuhong ^a   Wormald, Mark R ^b   Davis, Benjamin G ^a   Bayley, Hagan ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTES; CDS; DISSOCIATION RATE CONSTANT; ELECTRICAL RECORDING; GUEST MOLECULES; HOST-GUEST MOLECULAR RECOGNITION; HYDROPHOBIC CAVITIES; MOLECULAR SIMULATIONS; NMR SPECTROSCOPY; PROTEIN PORES; SINGLE OXYGEN ATOM; SINGLE-CHANNEL; STRUCTURAL PARAMETER; THREE-DIMENSIONAL STRUCTURE; WILD TYPES;

CYCLODEXTRINS; DISSOCIATION; HYDROPHOBICITY; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PROTEINS; SILANES; SUGARS;

RATE CONSTANTS;

ALPHA HEMOLYSIN; BETA CYCLODEXTRIN; DISULFIDE; OXYGEN; PROTEIN; SUGAR;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HETERONUCLEAR MULTIPLE BOND CORRELATION; NUCLEAR OVERHAUSER EFFECT; PROTEIN CONFORMATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

BETA-CYCLODEXTRINS; CARBOHYDRATE CONFORMATION; DISULFIDES; HEMOLYSIN PROTEINS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DYNAMICS SIMULATION; MUTATION; POROSITY; PROTEIN BINDING; PROTEIN CONFORMATION; STEREOISOMERISM;

EID: 79951535324     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1100867     Document Type: Article

References (74)

1. Szejtli, J. Chem. Rev. 1998, 98, 1743-1753
2. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1918
3. Dodziuk, H. Cyclodextrins and Their Complexes. Chemistry, Analytical Methods, Applications; Wiley-VCH: New York, 2006.
4. Davis, M. E.; Brewster, M. Nat. Rev. Drug Discovery 2004, 3, 1023-1035
5. Bom, A.; Bradley, M.; Cameron, K.; Clark, J. K.; van Egmond, J.; Feilden, H.; MacLean, E. J.; Muir, A. W.; Palin, R.; Rees, D. C.; Zhang, M.-Q. Angew. Chem., Int. Ed. 2002, 41, 265-270
6. Wenz, G.; Han, B. H.; Müller, A. Chem. Rev. 2006, 106, 782-817
7. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Chem. Rev. 2009, 109, 5974-6023
8. Chen, Y.; Liu, Y. Chem. Soc. Rev. 2010, 39, 495-505
9. Kuzuya, A.; Ohnishi, T.; Wasano, T.; Nagaoka, S.; Sumaoka, J.; Ihara, T.; Jyo, A.; Komiyama, M. Bioconjugate Chem. 2009, 20, 1643-1649
10. Ashcroft, B. A.; Spadola, Q.; Qamar, S.; Zhang, P.; Kada, G.; Bension, R.; Lindsay, S. Small 2008, 4, 1468-1475
11. Villaonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088-3116
12. Bayley, H.; Cremer, P. S. Nature 2001, 413, 226-230
13. Dekker, C. Nat. Nanotechnol. 2007, 2, 209-215
14. Song, L.; Hobaugh, M. R.; Shustak, C.; Cheley, S.; Bayley, H.; Gouaux, J. E. Science 1996, 274, 1859-1866
15. Braha, O.; Walker, B.; Cheley, S.; Kasianowicz, J. J.; Song, L.; Gouaux, J. E.; Bayley, H. Chem. Biol. 1997, 4, 497-505
16. Howorka, S.; Nam, J.; Bayley, H.; Kahne, D. Angew. Chem., Int. Ed. 2004, 43, 842-846
17. Bayley, H. Curr. Opin. Chem. Biol. 2006, 10, 628-637
18. Guan, X.; Gu, L.-Q.; Cheley, S.; Braha, O.; Bayley, H. ChemBioChem 2005, 6, 1875-1881
19. Wu, H. C.; Bayley, H. J. Am. Chem. Soc. 2008, 130, 6813-6819
20. Bayley, H.; Luchian, T.; Shin, S. H.; Steffensen, M. B. In Single Molecules and Nanotechnology; Rigler, R.; Vogel, H., Eds.; Springer: New York, 2008; pp 251 - 277.
21. Lu, S.; Li, W. W.; Rotem, D.; Mikhailova, E.; Bayley, H. Nat. Chem. 2010, 2, 921-928
22. Gu, L.-Q.; Braha, O.; Conlan, S.; Cheley, S.; Bayley, H. Nature 1999, 398, 686-690
23. Gu, L.-Q.; Cheley, S.; Bayley, H. Science 2001, 291, 636-640
24. Kang, X. F.; Cheley, S.; Guan, X.; Bayley, H. J. Am. Chem. Soc. 2006, 128, 10684-10685
25. Astier, Y.; Braha, O.; Bayley, H. J. Am. Chem. Soc. 2006, 128, 1705-1710
26. Gu, L.-Q.; Bayley, H. Biophys. J. 2000, 79, 1967-1975
27. Gu, L.-Q.; Cheley, S.; Bayley, H. J. Gen. Physiol. 2001, 118, 481-494
28. Banerjee, A.; Mikhailova, E.; Cheley, S.; Gu, L.-Q.; Montoya, M.; Nagaoka, Y.; Gouaux, E.; Bayley, H. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 8165-8170
29. Wu, H. C.; Astier, Y.; Maglia, G.; Mikhailova, E.; Bayley, H. J. Am. Chem. Soc. 2007, 129, 16142-16148
30. Clarke, J.; Wu, H. C.; Jayasinghe, L.; Patel, A.; Reid, S.; Bayley, H. Nat. Nanotechnol. 2009, 4, 265-270
31. Bornaghi, L.; Utille, J.-P.; Penninga, D.; Schmidt, A. K.; Dijkhuizen, L.; Schulz, G. E.; Driguez, H. Chem. Commun. 1996, 2541-2542
32. Morales, J. C.; Zurita, D.; Penades, S. J. Org. Chem. 1998, 63, 9212-9222
33. Kida, T.; Michinobu, T.; Zhang, W.; Nakatsuji, Y.; Ikeda, I. Chem. Commun. 2002, 1596-1597
34. Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265-287
35. Kikuzawa, A.; Kida, T.; Nakatsuji, Y.; Akashi, M. J. Org. Chem. 2005, 70, 1253-1261
36. Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638-1639
37. Kikuzawa, A.; Kida, T.; Akashi, M. Org. Lett. 2007, 9, 3909-3912
38. Kikuzawa, A.; Kida, T.; Akashi, M. Macromolecules 2008, 41, 3393-3395
39. Takeo, K.; Shinmitsu, K. Carbohydr. Res. 1984, 133, 135-145
40. Blanc-Muesser, M.; Driguez, H.; Lehmann, J.; Steck, J. Carbohydr. Res. 1992, 223, 129-136
41. Dong, H.; Pei, Z.; Ramstrom, O. J. Org. Chem. 2006, 71, 3306-3309
42. Varela, O.; Cicero, D.; Lederkremer, R. M. J. Org. Chem. 1989, 54, 1884-1890
43. Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem., Int. Ed. 2004, 43, 828-833
44. Yu, H. N.; Ling, C. C.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 2001, 832-837
45. Schneider, H. J.; Hacket, F.; Rüdiger, V.; Ikeda, H. Chem. Rev. 1998, 98, 1755-1786
46. Saenger, W.; Jacob, J.; Gessler, K.; Steiner, T.; Hoffmann, D.; Sanbe, H.; Koizumi, K.; Smith, S. M.; Takaha, T. Chem. Rev. 1998, 98, 1787-1802
47. Gessler, K.; Usón, I.; Takaha, T.; Krauss, N.; Smith, S. M.; Okada, S.; Sheldrick, G. M.; Saenger, W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4246-51
48. French, A. D.; Johnson, G. P. Carbohydr. Res. 2007, 342, 1223-1237
49. Keepers, J. W.; James, T. L. J. Magn. Reson. 1984, 57, 404-426
50. Thomas, P. D.; Basus, V. J.; James, T. L. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1237-1241
51. Tvaroska, I.; Hricovini, H.; Petrakova, E. Carbohydr. Res. 1989, 189, 359-362
52. Mulloy, B.; Frenkiel, T. A.; Davies, D. B. Carbohydr. Res. 1988, 184, 39-46
53. Cloran, F.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 1999, 121, 9843-9851
54. Steiner, T.; Koellner, G. J. Am. Chem. Soc. 1994, 116, 5122-5128
55. Naidoo, K. J.; Gamieldien, M. R.; Chen, J. Y.; Widmalm, G.; Maliniak, A. J. Phys. Chem. B 2008, 112, 15151-15157
56. Wormald, M. R.; Petrescu, A. J.; Pao, Y. L.; Glithero, A.; Elliott, T.; Dwek, R. A. Chem. Rev. 2002, 102, 371-386
57. Tan, X.; Lindenbaum, S. Int. J. Pharm. 1991, 74, 127-135
58. Yang, Z.; Breslow, R. Tetrahedron Lett. 1997, 38, 6171-6172
59. Cabrer, P. R.; Alvarez-Parrila, E.; Meijide, F.; Seijas, J. A.; Núñez, E. R.; Tato, J. V. Langmuir 1999, 15, 5489-5495
60. Movileanu, L.; Cheley, S.; Bayley, H. Biophys. J. 2003, 85, 897-910
61. Khan, A. R.; Forgo, P.; Stine, K. J.; DSouza, V. T. Chem. Rev. 1998, 98, 1977-1996
62. Hinrichs, W.; Saenger, W. J. Am. Chem. Soc. 1990, 112, 2789-2796
63. Saenger, W.; Niemann, C.; Herbst, R.; Hinrichs, W.; Steiner, T. Pure Appl. Chem. 1993, 65, 809-817
64. Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919-1958
65. Thornton, J. M. J. Mol. Biol. 1981, 151, 261-287
66. Quiocho, F. A. Annu. Rev. Biochem. 1986, 55, 287-315
67. Bush, C. A.; Martin-Pastor, M.; Imberty, A. Annu. Rev. Biophys. Biomol. Struct. 1999, 28, 269-293
68. Aachmann, F. L.; Otzen, D. E.; Larsen, K. L.; Wimmer, R. Protein Eng. 2003, 16, 905-912
69. Sujatha, M. S.; Sasidhar, Y. U.; Balaji, P. V. Biochemistry 2005, 44, 8554-8562
70. Brandl, M.; Weiss, M. S.; Jabs, A.; Sühnel, J.; Hilgenfeld, R. J. Mol. Biol. 2001, 307, 357-377
71. Thrippleton, M. J.; Keeler, J. Angew. Chem., Int. Ed. 2003, 42, 3938-3941
72. Edden, R. A. E.; Keeler, J. J. Magn. Reson. 2004, 166, 53-68
73. Hwang, T.-L.; Shaka, A. J. J. Am. Chem. Soc. 1992, 114, 3157-3159
74. Montal, M.; Mueller, P. Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 3561-3566