Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column

Analytical Chemistry

Volumn 75, Issue 3, 2003, Pages 535-542

  Massolini, Gabriella ^a   Calleri, Enrica ^a   Lavecchia, Antonio ^b   Loiodice, Fulvio ^c   Lubda, Dieter ^d   Temporini, Caterina ^a   Fracchiolla, Giuseppe ^c   Tortorella, Paolo ^e   Novellino, Ettore ^b   Caccialanza, Gabriele ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Dipartimento Farmaco Chimico   (Italy)

^d MERCK KGAA   (Germany)

^e UNIVERSITY OF CHIETI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROLYSIS; LIQUID CHROMATOGRAPHY; SILICA;

ENANTIOSELECTIVITY;

ESTERS;

ALKANOIC ACID; METHYL GROUP; PENICILLIN G;

ARTICLE; ENANTIOSELECTIVITY; ENZYME REACTOR; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; MATHEMATICAL ANALYSIS; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; MOLECULAR RECOGNITION; PROTEIN HYDROLYSIS; REACTION ANALYSIS;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYMES, IMMOBILIZED; ESTERS; HYDROLYSIS; PENICILLIN AMIDASE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 12244254474     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac0204193     Document Type: Article

References (40)

1. Duggleby, H. J.; Tolley, S. P.; Hill, C. P.; Dodson, E. J.; Moody, P. C. E. Nature 1995, 373, 264-268.
2. Fuganti, C.; Rosell, C. M.; Servi, S.; Tagliani, A.; Terreni, M. Tetrahedron Asymmetry 1992, 3, 383-386.
3. Rossi, D.; Calcagni, A.; Romeo, A.J. Org. Chem. 1979, 44, 2222-2225.
4. Rossi, D.; Romeo, A.; Lucente, G. J. Org. Chem. 1978, 43, 2576-2581.
5. Baldaro, E.; D'Arrigo, P.; Pedrocchi-Fantoni, G.; Rosell, C. M.; Servi, S.; Tagliani, A.; Terreni, M. Tetrahedron Asymmetry 1993, 4, 1031-1034.
6. Done, S. H.; Brannigan, J. A.; Moody, P. C. E.; Hubbard, R. E. J. Mol. Biol. 1998, 284, 463-475.
7. McVey, C. E.; Walsh, M. A.; Dodson, G. G.; Wilson, K. S.; Brannigan, J. A. J. Mol. Biol. 2001, 313, 139-150.
8. Brannigan, J. A.; Dodson, G.; Duggleby, H. J.; Moody, P. C. E.; Smith, J. L.; Tomchick, D. R.; Murzin, A. G. Nature 1995, 378, 416-419.
9. Mononen, I.; Fischer, K. J.; Kaartinen, V.; Aronson, N. N. FASEB J. 1993, 7, 1247-1256.
10. Löwe, J.; Stock, D.; Jap, B.; Zwickl, P.; Baumeister, W.; Huber, R. Science 1995, 268, 533-539.
11. Smith, J. L.; Zaluzec, E. J.; Wery, J. P.; Niu, L.; Switzer, R. L.; Zalkin, H.; Satow, Y. Science 1994, 264, 1427-1433.
12. Warshel, A.; Naray-Szabo, G.; Sussman. F.; Hwang, J.-K. Biochemistry 1989, 28, 3629-3637.
13. Daggett. V.; Schröder, S.; Kollman, P. J. J. Am. Chem. Soc. 1991, 113, 8926-8935.
14. Warshel, A.; Russell, S. J. Am. Chem. Soc. 1986, 108, 6569-6579.
15. Nakagawa, S.; Yu, H.-A.; Karplus, M.; Umeyama, H. Proteins 1993, 16, 172-194.
16. Kraut, J. Annu. Rev. Biochem. 1977, 46, 331-358.
17. Kaartinen, V.; Williams, J. C.; Tomich, J.; Yates, J. R.; Hood, L. E.; Mononen, I. J. Biol. Chem. 1991, 266, 5860-5869.
18. Seemüller, E.; Lupas, A.; Zühl, F.; Zwickl, P.; Baumeister, W. FEBS Lett. 1995, 359, 173-178.
19. Nakanishi, K.; Soga, N. J. Non Cryst. Solids 1992, 139, 1-13, 14-24.
20. Tanaka, N.; Kobayashi, H.; Ishizuka, N.; Minakuchi, H.; Nakanishi, K; Hosoya, K.; Ikegami, T. J. Chromatogr., A 2002, 965, 35-49.
21. Minakuchi, H.; Nakanishi, K; Soga, N.; Ishizuka, N.; Tanaka, N. Anal. Chem. 1996, 68, 3498-3501.
22. Cabrera, K; Lubda, D.; Eggenweiler, H-M.; Minakuchi, H.; Nakanishi, K. J. High Resolut. Chromatogr. 2000, 23, 99-104.
23. Romstedt, K. J.; Lei, L-P.; Feller, D. R.; Witiak, D. T.; Loiodice, F.; Tortorella, V. Farmaco 1996, 51, 107-114.
24. Bettoni, G.; Ferorelli, S.; Loiodice, F.; Tangari, N.; Tortorella, V.; Gasparrini, F.; Misifi, D.; Villani, C. Chirality 1992, 4, 193-203.
25. Ferorelli, S.; Loiodice, F.; Tortorella, V.; Amoroso, R.; Bettoni, G.; Conte-Camerino, D.; De Luca, A. Farmaco 1997, 52, 367-374.
26. Calleri, E.; Massolini, G.; Loiodice, F.; Fracchiolla, G.; Temporini, C.; Felix. G.; Tortorella, P.; Caccialanza, G. J. Chromatogr., A 2002, 958, 131-140.
27. Massolini, G.; Calleri, E.; De Lorenzi, E.; Pregnolato, M.; Terreni, M.; Felix, G.; Gandini, C. J. Chromatogr., A 2001, 921, 147-160.
28. Felix, G.; Descorps, V. Chromatographia 1999, 49, 595-605.
29. Andrisano, V.; Bartolini, M.: Gotti, R.: Cavrini, V.; Felix, G. J. Chromatogr., B 2001, 753, 375-383.
30. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
31. Sybyl Molecular Modelling System (version 6.8); Tripos Inc.: St. Louis, MO.
32. Vinter, J. G.; Davis, A.; Saunders, M. R. J. Comput.-Aided Mol. Des. 1987, 1, 31-55.
33. Gasteiger, J.; Marsili, M. Tetrahedron 1980, 36, 3219-3228.
34. Purcel, V. P.; Singer, J. A. J. Chem. Eng. Data 1967, 12, 235-246.
35. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784.
36. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J. B.; Meyer, E. F., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, T. J. Mol. Biol. 1977, 112, 535-542.
37. Jacobs, J.; Schultz, P. G.; Sugasawara, R; Powell, M. J. Am. Chem. Soc. 1987, 109, 2174-2176.
38. Hanson, J. E.; Kaplan, A. P.; Bartlett, P. A. Biochemistry 1989, 28, 6294-6305.
39. Burely, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
40. Burely, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189.