Dynamic enzymatic resolution of thioesters

Journal of the American Chemical Society

Volumn 120, Issue 23, 1998, Pages 5605-5610

  Um, Pil Je ^a   Drueckhammer, Dale G ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID ETHYL ESTER; ENZYME; ESTERASE; PROPIONIC ACID DERIVATIVE; PROTON; THIOESTER;

ARTICLE; DYNAMICS; ENZYME ACTIVITY; ENZYME SUBSTRATE; HYDROLYSIS; KINETICS;

EID: 0032540651     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980445b     Document Type: Article

References (27)

1. Kagan, H. B.; Fiaud, J. C. Topics Stereochem. 1988, 18, 249-330.
2. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; Krieger Publishing Co.: Malaber, FL, 1994.
3. Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989, 19, 63-125.
4. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584-2585.
5. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
6. Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1498.
7. Stecher, H.; Faber, K. Synthesis 1997, 1-16.
8. Ebbers, E. J.; Ariaans, G. j. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417-9476.
9. Tan, D. S.; Gunter, M. M.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 9093-9094.
10. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1992, 114, 10297-10302.
11. Gu, Q.-M.; Chen, C. S.; Sih, C. J. Tetrahedron Lett. 1986, 27, 1763-1766.
12. Lalonde, J. J.; Govardhan, C.; Khalaf, N.; Martinez, A. G.; Visuri, K.; Margolin, A. L. J. Am. Chem. Soc. 1995, 117, 6845-6852.
13. Moreno, J. M.; Samoza, A.; del Campo, C.; Llama, E. F.; Sinisterra, J. V. J. Mol. Catal., A: Chem. 1995, 95, 179-192.
14. Wells, P. R. Prog. Phys. Org. Chem. 1968, 6, 111-145.
15. Kreevoy, M. M.; Harper, E. T.; Duvall, R. E.; Wilgus, H. S., III.; Ditsch, L. T. J. Am. Chem. Soc. 1960, 82, 4899-4902.
16. Lyman, W. J. Handbook of Chemical Property Estimation Methods, American Chemical Society: Washington, DC, 1990; p 6-21.
17. Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119-251.
18. Janssen, M. J. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience Publishers: New York, 1969; pp 730-736.
19. Bianchi, D.; Cesti, P. J. Org. Chem. 1990, 55, 5657-5659.
20. Iriuchijima, S.; Kojima, N. J. Chem. Soc., Chem. Commun. 1981, 185-186.
21. Frykman, H.; Öhrner, N.; Norin, T.; Hult, K. Tetrahedron Lett. 1993, 34, 1367-1370.
22. Patel, R. N.; Howell, J. M.; McNamee, C. G.; Fortney, K. F.; Szarka, L. J. Biotechnol. Appl. Biochem. 1992, 16, 34-47.
23. Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1964, 86, 4651-4654.
24. Bruice, T. C.; Benkovic, S. J. Bioorganic Mechanisms; W. A. Benjamin: New York, 1966; pp 268-294.
25. Connors, K. A.; Bender, M. L. J. Org. Chem. 1961, 26, 2498-2504.
26. Akerfeldt, S. Acta Chem. Scand. 1960, 14, 1980-1984.
27. Fulwood, R.; Parker, D. Tetrahedron: Asymmetry 1992, 3, 25-28.