Substituent effect on the structural behavior of modified cyclodextrin: A molecular dynamics study on methylated β-CDs

Journal of Physical Chemistry B

Volumn 116, Issue 11, 2012, Pages 3477-3489

  Li, Wan Sheung ^a   Wang, San Chi ^a   Hwang, Tsong Song ^a   Chao, Ito ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; GLUCOSE; PHENOLS;

ANALYSIS APPROACH; CALIXARENES; CAVITY SHAPE; CD COMPLEX; CDS; CORRELATION ANALYSIS; CRYSTAL PACKINGS; DYNAMIC BEHAVIORS; FORCE FIELDS; GEOMETRIC DIMENSIONS; MACROCYCLIC STRUCTURE; MACROCYCLICS; MD SIMULATION; MODIFIED CYCLODEXTRINS; MOLECULAR DYNAMICS SIMULATIONS; STRUCTURAL BEHAVIORS; SUBSTITUENT EFFECT; WATER MODELS;

MOLECULAR DYNAMICS;

EID: 84858967418     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp207985q     Document Type: Article

References (62)

1. Fischer, E. Ber. Dtsch. Chem. Ges. 1894, 27, 2985-2993
2. Cram, D. J. Angew. Chem. 1986, 98, 1041-1060
3. Angew. Chem., Int. Ed. 1986, 25, 1039-1057.
4. Koshland, D. E., Jr. Proc. Natl. Acad. Sci. U. S. A. 1958, 44, 98-104
5. Easson, L. H.; Stedman, E. Biochem. J. 1933, 27, 1257-1266
6. Dalgliesh, C. E. J. Chem. Soc. 1952, 3, 3940-3942
7. Pirkle, W. H.; Pochapsky, T. C. Chem. Rev. 1989, 89, 347-362
8. Kano, K. J. Phys. Org. Chem. 1997, 10, 286-291
9. Inoue, Y. Annu. Rep. NMR Spectrosc. 1993, 27, 59-101
10. Czugler, M.; Eckle, E.; Stezowski, J. J. Chem. Soc., Chem. Commun. 1981, 1291-1922
11. Aree, T.; Saenger, W.; Leibnitz, P.; Hoier, H. Carbohydr. Res. 1999, 315, 199-205
12. Harata, K. Bull. Chem. Soc. Jpn. 1988, 61, 1939-1944
13. Aree, T.; Hoier, H.; Schulz, B.; Reck, G..; Saenger, W. Angew. Chem., Int. Ed. 2000, 39, 897-899
14. Selkti, M.; Navaza, A.; Villain, F.; Charpin, P.; De Rango, C. J. Inclusion Phenom. Macrocyclic Chem. 1997, 27, 1-12
15. Harata, K. J. Chem. Soc., Chem. Commun. 1993, 546-547
16. Harata, K. Chem. Commun. 1999, 191-192
17. Steiner, T.; Saenger, W. Carbohydr. Res. 1995, 275, 73-82
18. Stezowski, J. J.; Parker, W.; Hilgenkamp, S.; Gdaniec, M. J. Am. Chem. Soc. 2001, 123, 3919-3926
19. Aree, T.; Hoier, H.; Reck, G..; Saenger, S. Angew. Chem., Int. Ed. 2000, 39, 897-899
20. Tsorteki, F.; Mentzafos, D. Carbohydr. Res. 2002, 337, 1229-1232
21. Harata, K.; Uekama, K.; Otagiri, M.; Hirayama, F. Bull. Chem. Soc. Jpn. 1983, 56, 1732-1736
22. Harata, K.; Uekama, K.; Imai, T.; Hirayama, F.; Otagiri, M. J. Inclusion Phenom. Macrocyclic Chem. 1988, 6, 443-460
23. Harata, K. J. Chem. Soc., Chem. Commun. 1988, 928-929
24. Harata, K.; Hirayama, F.; Arima, H.; Uekama, K.; Miyaji, T. J. Chem. Soc., Perkin Trans. 2 1992, 1159-1166
25. Caira, M. R.; Griffith, V. J.; Nassimbeni, L. R.; van Oudtshoorn, B. J. Chem. Soc., Perkin Trans. 2 1994, 2071-2072
26. Steiner, T.; Saenger, W. Angew. Chem., Int. Ed. 1998, 37, 3404-3407
27. Mentzafos, D.; Mavridis, I. M.; Schenk, H. Carbohydr. Res. 1994, 253, 39-50
28. Brown, G. R.; Caira, M. R.; Nassimbeni, L.; van Oudtshoorn, B. J. Inclusion Phenom. Macrocyclic Chem. 1996, 26, 281-294
29. Caira, M. R.; Griffith, V. J.; Nassimbeni, L. R.; van Oudtshoorn, B. J. Inclusion Phenom. Macrocyclic Chem. 1995, 20, 277-290
30. Makedonopoulou, S.; Yannakopoulou, K.; Mentzafos, D.; Lamzin, V.; Popov, A.; Mavridis, I. M. Acta Crystallogr. 2001, B57, 399-409
31. Rontoyianni, A.; Mavridis, I. M.; Israel, R.; Beurskens, G. J. Inclusion Phenom. Macrocyclic Chem. 1998, 32, 415-428
32. Cardinael, P.; Peulon, V.; Perez, G.; Coquerel, G.; Toupet, L. J. Inclusion Phenom. Macrocyclic Chem. 2001, 39, 159-167
33. Immel, S.; Fujita, K.; Lichtenthaler, F. W. Chem.-Eur. J. 1999, 5, 3185-3192
34. Fujita, K.; Chen, W.-H.; Yuan, D.-Q.; Nogami, Y.; Koga, T.; Fujioka, T.; Mihashi, K.; Immel, S.; Lichtenthaler, F. W. Tetrahedron: Asymmetry 1999, 10, 1689-1696
35. Lichtenthaler, F. W.; Immel, S. Tetrahedron: Asymmetry 1994, 5, 2045-2060
36. Lindner, H. J.; Yuan, D.-Q.; Fujita, K.; Kubo, K.; Lichtenthaler, F. W. Chem. Commun. 2003, 1730-1731
37. Kida, T.; Michinobu, T.; Zhang, W.; Nakatsuji, Y.; Ikeda, I. Chem. Commun. 2002, 1596-1597
38. Morales, J. C.; Zurita, D.; Penadés, S. J. Org. Chem. 1998, 63, 9212-9222
39. Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265-287
40. Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638-1639
41. Kikuzawa, A.; Kida, T.; Akashi, M. Org. Lett. 2007, 9, 3909-3912
42. Li, W.-W.; Claridge, T. D.W.; Li, Q.; Wormald, M. R.; Davis, B. G.; Bayley, H. J. Am. Chem. Soc. 2011, 133, 1987-2001
43. Bornaghi, L.; Utille, J.-P.; Penninga, D.; Schmidt, A. K.; Dijkhuizen, L.; Schulz, G. E.; Driguez, H. Chem. Commun. 1996, 2541-2542
44. Kikuzawa, A.; Kida, T.; Nakatsuji, Y.; Akashi, M. J. Org. Chem. 2005, 70, 1253-1261
45. Reibenspies, J. H.; Maynard, D. K.; Derecskei-Kovacs, A.; Vigh, G. Carbohydr. Res. 2000, 328, 217-227
46. Añibarro, M.; Gessler, K.; Usón, I.; Sheldrick, G. M.; Harata, K.; Uekama, K.; Hirayama, F.; Abe, Y.; Saenger, W. J. Am. Chem. Soc. 2001, 123, 11854-11862
47. MacroModel, Interactive Molecular Modeling System, Version 6.5, BatchMin, Columbia University, NY. MacroModel Version 9.0, Schrodinger, LLC, New York, NY, 2011.
48. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Chio, C.; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784
49. Weiner, S. J.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 1986, 7, 230-252
50. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129
51. Qiu, D.; Shenkin, P. S.; Hollinger, F. P.; Still, W. C. J. Phys. Chem. A 1997, 101, 3005-3014
52. Weiser, J.; Weiser, A. A.; Shenkin, P. S.; Still, W. C. J. Comput. Chem. 1998, 19, 797-808
53. Weiser, J.; Weiser, A. A.; Shenkin, P. S.; Still, W. C. J. Comput. Chem. 1998, 19, 1110
54. Stigler, S. M. Francis Galton's Account of the invention of Correlation Stat. Sci. 1989, 4 (2) 73-79
55. Cloran, F.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 1999, 121, 9843-9851
56. Szejtli, J. Chem. Rev. 1998, 98, 1743-1753
57. Reibenspies, J. H.; Maynard, D. K.; Derecskei-Kovacs, A.; Vigh, G. Carbohydr. Res. 2000, 328, 217-227
58. Analyses of 160 crystal structures with 112 CD dimers and 48 monomers were obtained from The Cambridge Crystallographic Data Centre. http://www.ccdc.cam.ac.uk (accessed March, 2011). New software for searching the Cambridge Structural Database and visualising crystal structures. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389-397
59. Thaning, J.; Stevensson, B.; Ostervall, J.; Naidoo, K. J.; Widmalm, G.; Maliniak, A. J. Phys. Chem. B 2008, 112, 8434-8436
60. Naidoo, K. J.; Gamieldien, M. R.; Chen, J. Y.-J.; Widmalm, G.; Maliniak, A. J. Phys. Chem. B 2008, 112, 15151-15157
61. Schneider, H.-J.; Hacket, F.; Rudiger, V. Chem. Rev. 1998, 98, 1755-1784
62. Gelb, R. I.; Schartz, L. M.; Johnson, R. F.; Laufer, D. A. J. Am. Chem. Soc. 1978, 100, 3553-3559