Chiral separation of racemic phenylglycines in thermolysin crystal: A molecular simulation study

Journal of Physical Chemistry B

Volumn 113, Issue 48, 2009, Pages 15851-15857

  Hu, Zhongqiao ^a   Jiang, Jianwen ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; CHROMATOGRAPHIC ANALYSIS; COMPUTER SIMULATION; DRUG PRODUCTS PLANTS; ENANTIOSELECTIVITY; LIQUID CHROMATOGRAPHY; MACHINE DESIGN; STRUCTURAL ANALYSIS;

CHIRAL CENTERS; CHIRAL DISCRIMINATION; CHIRAL SEPARATIONS; CHIRAL STATIONARY PHASE; ELUTION ORDER; ENANTIOSEPARATIONS; L-PHENYLGLYCINE; MOBILE PHASE; MOLECULAR SIMULATIONS; OPTIMIZATION OF SEPARATION; PHARMACEUTICAL INDUSTRY; PHENYLGLYCINES; RATIONAL DESIGN; STATIONARY PHASIS; THERMOLYSIN; UNDERLYING MECHANISM; WATER ACT;

PHASE SEPARATION;

EID: 72149084118     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9055889     Document Type: Article

References (44)

1. McConnell, O.; Bach, A.; Balibar, C.; Byrne, N.; Cai, Y. X.; Carter, G.; Chlenov, M.; Di, L.; Fan, K.; Goljer, I.; He, Y. N.; Herald, D.; Kagan, M.; Kerns, E.; Koehn, F.; Kraml, C.; Marathias, V.; Marquez, B.; McDonald, L.; Nogle, L.; Petucci, C.; Schlingmann, G.; Tawa, G.; Tischler, M.; Williamson, R. T.; Sutherland, A.; Watts, W.; Young, M.; Zhang, M. Y.; Zhang, Y. R.; Zhou, D. H.; Ho, D. Chirality 2007, 19, 658.
2. Lipkowitz, K. B.; Coner, R.; Peterson, M. A. J. Am. Chem. Soc. 1997, 119, 11269.
3. Lipkowitz, K. B. Acc. Chem. Res. 2000, 33, 555.
4. Zhao, C.; Cann, N. M. J. Chromatogr. A 2006, 1131, 110.
5. Zhao, C. F.; Cann, N. M. J. Chromatogr. A 2007, 1149, 197.
6. Zhao, C. F.; Cann, N. M. Anal. Chem. 2008, 80, 2426.
7. Nita, S.; Cann, N. M. J. Phys. Chem. B 2008, 112, 13022.
8. Szabelski, P. Appl. Surf. Sci. 2007, 253, 5387.
9. Szabelski, P.; Sholl, D. S. J. Chem. Phys. 2007, 126, 144709.
10. Kasat, R. B.; Wang, N. H. L.; Franses, E. I. J. Chromatogr. A 2008, 1190, 110.
11. Kasat, R. B.; Wee, S. Y.; Loh, J. X.; Wang, N. H. L.; Franses, E. I. J. Chromatogr. B 2008, 875, 81.
12. Haginaka, J. J. Chromatogr. A 2001, 906, 253.
13. Vilenchik, L. Z.; Griffith, J. P.; St. Clair, N.; Navia, M. A.; Margolin, A. L. J. Am. Chem. Soc. 1998, 120, 4290.
14. Margolin, A. L.; Navia, M. A. Angew. Chem., Int. Ed. 2001, 40, 2205.
15. Falkner, J. C.; Al-Somali, A. M.; Jamison, J. A.; Zhang, J. Y.; Adrianse, S. L.; Simpson, R. L.; Calabretta, M. K.; Radding, W.; Phillips, G. N.; Colvin, V. L. Chem. Mater. 2005, 17, 2679.
16. Roy, J. J.; Abraham, T. E. Chem. Rev. 2004, 104, 3705.
17. Lee, T. S.; Vaghjiani, J. D.; Lye, G. J.; Turner, M. K. Enzyme Microb. Technol. 2000, 26, 582.
18. Pastinen, O.; Jokela, J.; Eerikainen, T.; Schwabe, T.; Leisola, M. Enzyme Microb. Technol. 2000, 26, 550.
19. Leisola, M.; Jokela, J.; Finell, J.; Pastinen, O. Biotechnol. Bioeng. 2001, 72, 501.
20. Jokela, J.; Pastinen, O.; Leisola, M. Enzyme Microb. Technol. 2002, 31, 67.
21. Cvetkovic, A.; Straathof, A. J. J.; Hanlon, D. N.; Van der Zwaag, S.; Krishna, R.; Van der Wielen, L. A. M. Biotechnol. Bioeng. 2004, 86, 389.
22. Cvetkovic, A.; Picioreanu, C.; Straathof, A. J. J.; Krishna, R.; van der Wielent, L. A. M. J. Am. Chem. Soc. 2005, 127, 875.
23. Malek, K.; Coppens, M. O. J. Phys. Chem. B 2008, 112, 1549.
24. Hu, Z. Q.; Jiang, J. W. Langmuir 2008, 24, 4215.
25. Hu, Z. Q.; Jiang, J. W. Biophys. J. 2008, 95, 4148.
26. Hu, Z. Q.; Jiang, J. W. J. Membr. Sci. 2008, 324, 192.
27. Hu, Z. Q.; Jiang, J. W. J. Chromatogr. A 2009, 1216, 5122.
28. Hausrath, A. C.; Matthews, B. W. Acta Crystallogr. Sect. D-Biol. Crystallogr. 2002, 58, 1002.
29. Schuler, L. D.; Daura, X.; Van Gunsteren, W. F. J. Comput. Chem. 2001, 22, 1205.
30. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; Hermans, J. Interaction models for water in relation to protein hydration. In Intermolecular Forces; Pullman, B., Ed.; D. Reidel Publishing Co.: Dordrecht, The Netherlands, 1981; pp 331.
31. Van der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. C. J. Comput. Chem. 2005, 26, 1701.
32. Darden, T.; York, D.; Pedersen, L. J. Chem. Phys. 1993, 98, 10089.
33. Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. J. Chem. Phys. 1995, 103, 8577.
34. Hess, B.; Bekker, H.; Berendsen, H. J. C.; Fraaije, J. J. Comput. Chem. 1997, 18, 1463.
35. Miyamoto, S.; Kollman, P. A. J. Comput. Chem. 1992, 13, 952.
36. Koplik, J.; Banavar, J. R.; Willemen, J. F. Phys. Rev. Lett. 1988, 60, 1282.
37. Siu, S. W. I.; Bockmann, R. A. J. Struct. Biol., 2007, 157, 545.
38. Wang, S. H.; Cann, N. M. J. Chem. Phys. 2009, 130, 244701.
39. Szaleniec, M.; Dudzik, A.; Pawul, M.; Kozik, B. J. Chromatogr. A 2009, 1216, 6224.
40. Zhao, C. F.; Diemert, S.; Cann, N. M. J. Chromatogr. A 2009, 1216, 5968.
41. Job, G. E.; Shvets, A.; Pirkle, W. H.; Kuwahara, S.; Kosaka, M.; Kasai, Y.; Taji, H.; Fujita, K.; Watanabe, M.; Harada, N. J. Chromatogr. A 2004, 1055, 41.
42. Wolf, C.; Pranatharthiharan, L.; Volpe, E. C. J. Org. Chem. 2003, 68, 3287.
43. Hyun, M. H.; Ryoo, J. J.; Pirkle, W. H. J. Chromatogr. A 2000, 886, 47.
44. Van der Spoel, D.; Lindahl, E.; Hess, B.; et al. Gromacs User Mannal V3.3, 2006.