Insights into the solvent dependence of chymotryptic prochiral selectivity

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4259-4263

  Ke, Tao ^a   Klibanov, Alexander M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 PROPANEDIOL; CHYMOTRYPSIN; SOLVENT; VINYL ACETATE;

ACYLATION; ARTICLE; CATALYSIS; CHIRALITY; COMPUTER MODEL; ENZYME CONFORMATION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SPECIFICITY;

EID: 0032513720     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9802201     Document Type: Article

References (29)

1. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1-9. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70.
2. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1-9. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70.
3. Koskinen, A. M. P.; Klibanov, A. M., Eds.; Enzymatic Reactions in Organic Media; Blackie: London, 1996.
4. Poppe, L.; Novak, L. Selective Biocatalysis; VCH Publishers: New York, 1992. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Publishers: New York, 1995. Faber, K. Biotransformations in Organic Chemisry; Springer-Verlag: Berlin, 1996.
5. Poppe, L.; Novak, L. Selective Biocatalysis; VCH Publishers: New York, 1992. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Publishers: New York, 1995. Faber, K. Biotransformations in Organic Chemisry; Springer-Verlag: Berlin, 1996.
6. Poppe, L.; Novak, L. Selective Biocatalysis; VCH Publishers: New York, 1992. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Publishers: New York, 1995. Faber, K. Biotransformations in Organic Chemisry; Springer-Verlag: Berlin, 1996.
7. Poppe, L.; Novak, L. Selective Biocatalysis; VCH Publishers: New York, 1992. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Publishers: New York, 1995. Faber, K. Biotransformations in Organic Chemisry; Springer-Verlag: Berlin, 1996.
8. Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157-7160. Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M J. Am. Chem. Soc. 1993, 115, 390-396. Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 91-132.
9. Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157-7160. Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M J. Am. Chem. Soc. 1993, 115, 390-396. Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 91-132.
10. Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157-7160. Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M J. Am. Chem. Soc. 1993, 115, 390-396. Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 91-132.
11. Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366-3374.
12. Chen, C-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299. Straathof, A. J. J.; Jongejan, J. A. Enzyme Microbial Technol. 1997, 21, 559-571.
13. Chen, C-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299. Straathof, A. J. J.; Jongejan, J. A. Enzyme Microbial Technol. 1997, 21, 559-571.
14. Yennawar, N. H.; Yennawar, H. P.; Farber, G. K. Biochemistry 1994, 33, 7326-7336. Yennawar, H. P.; Yennawar, N. H.; Farber, G. K. J. Am. Chem. Soc. 1995, 117, 577-585.
15. Yennawar, N. H.; Yennawar, H. P.; Farber, G. K. Biochemistry 1994, 33, 7326-7336. Yennawar, H. P.; Yennawar, N. H.; Farber, G. K. J. Am. Chem. Soc. 1995, 117, 577-585.
16. Wescott, C. R.; Noritomi, H.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 10365-10370.
17. Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 10362-10363.
18. Chatterjee, S.; Russell, A. J. Biotechnol. Bioeng. 1992, 40, 1069-1077.
19. Throughout this paper, we use double-logarithmic coordinates to give equal weight to all experimental points. Given a wide range in which the measured parameters vary (Table 1), linear coordinates would not afford such a possibility.
20. Stoddard, B. L.; Bruhnke, J.; Porter, N.; Ringe, D.; Petsko, G. A. Biochemistry 1990, 29, 4871-4876.
21. Schmitke, J. L.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3360-3365.
22. Warshel, A.; Naray-Szabo, G.; Sussman, F.; Hwang, J.-K. Biochemistry 1989, 28, 3629-3637.
23. Connolly, M. L. Science 1983, 221, 709-712.
24. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.
25. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.
26. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.
27. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.
28. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.
29. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equi-libria Using UNIFAC; Elsevier: New York, 1977. Steen, S.-J.; Bärbel, K.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1979, 18, 714-722. Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1982, 21, 118-127. Macedo, E. A.; Weidlich, U.; Gmehling, J.; Rasmussen, P. Ind. Eng. Chem. Proc. Des. Dev. 1983, 22, 676-678. Tiegs, D.; Gmehling, J.; Rasmussen, P.; Fredenslund, A. Ind. Eng. Chem. Proc. Des. Dev. 1987, 26, 159-161. Hansen, H. K.; Rasmussen, P.; Schiller, M.; Gmehling, J. Ind. Eng. Chem. Res. 1991, 30, 2352-2355.