Quick E. A Fast Spectrophotometric Method to Measure the Enantioselectivity of Hydrolases

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4560-4561

  Janes, Lana E ^a   Kazlauskas, Romas J ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342754143     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707803     Document Type: Article

References (19)

1. Roberts, S. M., Ed. Preparative Biotransformations; Wiley: New York, 1992-1997. Faber, K Biotransformations in Organic Chemistry, 2nd ed.; Springer: Berlin, 1995.
2. Roberts, S. M., Ed. Preparative Biotransformations; Wiley: New York, 1992-1997. Faber, K Biotransformations in Organic Chemistry, 2nd ed.; Springer: Berlin, 1995.
3. Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985; pp 103-106.
4. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
5. (a) Jongejan, J. A.; van Tol, J. B. A.; Geerlof, A.; Duine, J. A. Recl. Trav. Chim. Pays-Bas 1991, 110, 247-254.
6. (b) van Tol, J. B. A.; Jongejan, J. A.; Geerlof, A.; Duine, J. A. Recl. Trav. Chim. Pays-Bas 1991, 110, 255-262.
7. (a) Lu, Y.; Zhao, X.; Chen, Z. N. Tetrahedron: Asymmetry 1995, 6, 1093-1096.
8. (b) Rakels, J. L. L.; Romein, B.; Straathof, A. J. A.; Heijnen, J. J. Biotechnol. Bioeng. 1993, 43, 411-422.
9. (c) Fourneron, J. D.; Combemel, A.; Buc, J.; Piéroni, G. Tetrahedron Lett. 1992, 33, 2469-2472.
10. (a) Berman, J.; Green, M.; Sugg, E.; Anderegg, R.; Millington, D. S.; Norwood, D. L.; McGeehan, J.; Wiseman, J. J. Biol. Chem. 1992, 267, 1434-1437.
11. (b) Petithorny, J. R.; Masiarz, F. R.; Kirsch, J. F.; Santi, D. V. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 11510-11514.
12. Schellenberger, V.; Siegel, R. A.; Rutter, W. J. Biochemistry 1993, 32, 4344-4348.
13. s = 1.66). For analysis, samples of 1 were hydrolyzed to the acid in aqueous NaOH.
14. Wu, S. H.; Guo, Z. W.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 1990-1995; van der Lugt, J. P.; Elfrink, H.; Evenaar, J.; Doddema, H. J. In Microbial Reagents in Organic Synthesis; Servi, S., Ed.; Kluwer Academic: Dordrecht, 1992; pp 261-272.
15. Wu, S. H.; Guo, Z. W.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 1990-1995; van der Lugt, J. P.; Elfrink, H.; Evenaar, J.; Doddema, H. J. In Microbial Reagents in Organic Synthesis; Servi, S., Ed.; Kluwer Academic: Dordrecht, 1992; pp 261-272.
16. Resorufin acetate can also serve as a reference compound. Previous use of resorufin acetate as a chromogenic lipase substrate: Kramer, D. N.; Guilbault, G. G. Anal. Lett. 1964, 36, 1662-1663. Herrmann, R. Chimia 1991, 45, 317-318.
17. Resorufin acetate can also serve as a reference compound. Previous use of resorufin acetate as a chromogenic lipase substrate: Kramer, D. N.; Guilbault, G. G. Anal. Lett. 1964, 36, 1662-1663. Herrmann, R. Chimia 1991, 45, 317-318.
18. Moore, J. C.; Arnold, F. H. Nature Biotechnol. 1996, 14, 458-468.
19. Due to assumptions made in deriving eq 1, both the endpoint method and quick E will give inaccurate enantioselectivities in two common situations-impure biocatalyst and reactions inhibited by product.