Molecular Modeling of Enantio-discrimination of α-Methoxy-α -trifluoromethylphenylacetic Acid (MTPA) by Cyclomaltoheptaose (β-Cyclodextrin) and 6-Amino-6-deoxy-cyclomaltoheptaose

Bulletin of the Korean Chemical Society

Volumn 24, Issue 11, 2003, Pages 1627-1631

  Jung, Eunkyoung ^a   Jeong, Karpjoo ^a   Lee, Sangsan ^b   Kim, Jee In ^a   Jung, Seunho ^a  

^a Konkuk University   (South Korea)

^b Korea Institute of Science and Technology Information (KISTI)   (South Korea)

Author keywords

Chiral recognition; Cyclodextrin; Inclusion complex; Molecular modeling

Indexed keywords

6 AMINO 6 DEOXYCYCLOMALTOHEPTAOSE; ALPHA METHOXY ALPHA TRIFLUOROMETHYLPHENYLACETIC ACID; BETA CYCLODEXTRIN; HEPTOSE; MALTOSE; PHENYLACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR RECOGNITION; MONTE CARLO METHOD; THERMODYNAMICS;

EID: 0347635452     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.11.1627     Document Type: Article

References (29)

1. Amstrong, D. W.; Ward, T. J.; Armstrong, R. D.; Beesley, T. E. Science 1986, 232, 1132.
2. Redondo, J.; Blazquez, M. A.; Torrens, A. Chirality 1999, 11, 694.
3. Hamilton, J. A.; Chen, L. J. Am. Chem. Soc. 1998, 110, 5833.
4. Berthod, A.; Jin, H. L.; Beesley, T. E.; Duncan, J. D.; Amstrong, D. W. J. Pharm. Biomed, Anal. 1990, 8, 123.
5. Pergaman; Comprehensive Supramolecular Chemistry in Cyclodextrin; Szejtli, J., Osa, T., Eds.; Oxford, U. K., 1996; Vol. 3.
6. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
7. Roseman, M.; Jencks, W. P. J. Am. Chem. Soc. 1975, 97, 631
8. Connors, K. A. Chem. Rev. 1997, 97, 1325.
9. Rekharsky, M. V.; Inoue, Y. J. Am. Chem. Soc. 2002, 124, 813.
10. Kitae, T.; Takashima, H.; Kano, K. J. Inclusion Phenom. Macrocyclic Chem. 1999, 33, 345.
11. Kitae, T.; Nakayama, T.; Kano, K. J. Chem. Soc., Perkin Trans. 2 1998, 207.
12. Kano, T. J. Phys. Org. Chem. 1997, 10, 286.
13. Brown, S. E.; Coates, J. H.; Duckworth, P. A.; Lincoln, S. F.; Easton, C. J.; May, B. L. J. Chem. Soc. 1993, 89, 1035.
14. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
15. Kim, H.; Choi, J.; Kim, H.-W.; Jung, S. Carbohydr. Res. 2002, 337, 549.
16. Dauber-Osguthorpe, P.; Roberts, V. A.; Osguthorpe, D. J.; Wolff, J.; Genest, M.; Hagler, A. T. Proteins 1988, 4, 31.
17. Betzel, C.; Saenger, W.; Hingerty, B. E.; Brown, G. M. J. Am. Chem. Soc. 1984, 106, 7545.
18. Choi, Y.; Kang, S.; Yang, C.-H.; Kim, H.-W.; Jung, S. Bull. Korean Chem. Soc. 1999, 20, 753.
19. Choi, Y.; Yang, C.-H.; Kim, H.-W.; Jung, S. Carbohydr. Res. 2000, 326, 227.
20. Choi, Y.; Yang, C.-H.; Kim, H.-W.; Jung, S. Carbohydr. Res. 2000, 328, 393.
21. Hart, T. N.; Read, R. J. Proteins 1992, 13, 206.
22. Metropolis, N.; Rosenbluth, A. W.; Rosenbluth, M. N.; Teller, A. H.; Teller, E. J. Chem. Phys. 1953, 21, 1087.
23. Choi, Y.; Yang, C.-H.; Kim, H.-W.; Jung, S. J. Incl. Phenom. 2001, 39, 71.
24. Kim, H.; Kang, S.; Jung, S. Bull. Korean Chem. Soc. 2001, 22, 979.
25. Kim, H.; Jeong, K.; Lee, S.; Jung, S. Bull. Korean Chem. Soc. 2003, 24, 1.
26. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684.
27. Luty, B. A.; Wasserman, Z. R.; Stouten, P. F. W.; Hodge, C. N.; Zacharias, M.; McCammon, J. A. J. Comp. Chem. 1995, 16, 454.
28. Shiona, F.; Kusaka, H.; Wada, K.; Azami, H.; Yasunami, M.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Org. Chem. 1998, 63, 920.
29. Rekharsky, M. V.; Inoue, Y. J. Am. Chem. Soc. 2000, 122, 4418.