Molecular dynamics (MD) simulations for the prediction of chiral discrimination of N-acetylphenylalanine enantiomers by cyclomaltoheptaose (β-cyclodextrin, β-CD) based on the MM-PBSA (molecular mechanics-Poisson-Boltzmann surface area) approach

Carbohydrate Research

Volumn 339, Issue 11, 2004, Pages 1961-1966

  Choi, Youngjin ^a   Jung, Seunho ^a  

^a Konkuk University   (South Korea)

Author keywords

Chiral discrimination; Cyclodextrin; Molecular dynamics simulations; Molecular mechanics

Indexed keywords

AROMATIC COMPOUNDS; COMPUTER SIMULATION; CONFORMATIONS; POISSON DISTRIBUTION;

CHIRAL DISCRIMINATION; CONFORMATIONAL PROPERTIES; ENANTIOMERS;

MOLECULAR DYNAMICS;

ACETIC ACID DERIVATIVE; BETA CYCLODEXTRIN; HEPTOSE; MALTOSE; PHENYLALANINE DERIVATIVE;

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; ENANTIOSELECTIVITY; EXPERIMENTAL TEST; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; POISSON DISTRIBUTION; PREDICTION; PRIORITY JOURNAL; SIMULATION; SURFACE PROPERTY; TECHNIQUE;

BETA-CYCLODEXTRINS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENYLALANINE; STEREOISOMERISM; THERMODYNAMICS;

EID: 3142740828     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.05.026     Document Type: Article

References (33)

1. D'Souza V.T., Lipkowitz K.B. Chem. Rev. 98:1998;1741-2076
2. Singh M., Sharma R., Banerjee U.C. Biotechnol. Adv. 20:2002;341-359
3. Kim H., Jeong K., Lee S., Jung S. J. Comput. Aided Mol. Des. 16:2002;601-610
4. Stella V.J., Rao V.M., Zannou E.A., Zia V. Adv. Drug Delivery Rev. 36:1999;3-16
5. Schneiderman E., Stalcup A.M. J. Chromatogr. B. 745:2000;83-102
6. Armstrong D.W., Ward T.J., Armstrong R.D., Beesley T.E. Science. 232:1986;1132-1135
7. Cram D.J. Science. 240:1988;760-767
8. Lipkowitz K.B. Chem. Rev. 98:1998;1829-1873
9. Lee S., Jung S. Carbohydr. Res. 338:2003;1143-1146
10. Maier N.M., Schefzick S., Lombardo G.M., Feliz M., Rissanen K., Lindner W., Lipkowitz K.B. J. Am. Chem. Soc. 124:2002;8611-8629
11. Lipkowitz K.B., Coner R., Peterson M.A. J. Am. Chem. Soc. 119:1997;11269-11276
12. Dodziuk H., Lukin O. Chem. Phys. Lett. 327:2000;18-22
13. Srinivasan J., Cheatham T.E., Cieplak P., Kollman P.A., Case D.A. J. Am. Chem. Soc. 120:1998;9401-9409
14. Huo S., Massova I., Kollman P.A. J. Comput. Chem. 23:2002;15-27
15. Bea I., Jaime C., Kollman P.A. Theor. Chem. Acc. 108:2002;286-292
16. Gouda H., Kuntz I.D., Case D.A., Kollman P.A. Biopolymers. 68:2003;16-34
17. Wang J., Morin P., Wang W., Kollman P.A. J. Am. Chem. Soc. 123:2001;5221-5230
18. Kuhn B., Kollman P.A. J. Med. Chem. 43:2000;3786-3791
19. Clark J.L., Stezowski J.J. J. Am. Chem. Soc. 123:2001;9880-9888
20. Rekharsky M.V., Inoue Y. J. Am. Chem. Soc. 124:2002;12361-12371
21. Rekharsky M.V., Inoue Y. J. Am. Chem. Soc. 124:2002;813-826
22. Alexander J.M., Clark J.L., Brett T.J., Stezowski J.J. Proc. Natl. Acad. Sci. U.S.A. 99:2002;5115-5120
23. Inoue Y. Ann. Rep. NMR Spectrosc. 27:1993;59-101
24. Takahashi S., Suzuki E., Nagashima N. Bull. Chem. Soc. Jpn. 59:1986;1129-1132
25. Brooks B.R., Bruccoleri R.E., Olafson B.D., States D.J., Swaminathan S., Karplus M. J. Comput. Chem. 4:1983;187-217
26. Kirschner K.N., Woods R.J. Proc. Natl. Acad. Sci. U.S.A. 98:2001;10541-10545
27. Kano K. J. Phys. Org. Chem. 10:1997;286-291
28. Jorgensen W.L. J. Chem. Phys. 77:1982;4156-4163
29. Darden T., York D., Pedersen L. J. Chem. Phys. 98:1993;10089-10092
30. Ryckaert J.P., Ciccotti G., Berendsen H.J.C. J. Comput. Phys. 23:1977;327-341
31. Feller S.E., Zhang Y., Pastor R.W., Brooks B.R. J. Chem. Phys. 103:1995;4613-4621
32. Sitkoff D., Sharp K.A., Honig B. J. Phys. Chem. 98:1994;1978-1988
33. Wang W., Lim W.A., Jakalian A., Wang J., Wang J., Luo R., Bayly C.I., Kollman P.A. J. Am. Chem. Soc. 123:2001;3986-3994