Asymmetric synthesis of β-hydroxy esters and α-alkyl-β-hydroxy esters by recombinant Escherichia coli expressing enzymes from baker's yeast

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2586-2587

  Rodríguez, Sonia ^a   Schroeder, Kersten T ^a   Kayser, Margaret M ^b   Stewart, Jon D ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ESTER DERIVATIVE; HYDROXYL GROUP;

CHEMICAL REACTION; ENZYME SYNTHESIS; ESCHERICHIA COLI; GENE EXPRESSION; NONHUMAN; NOTE; SACCHAROMYCES CEREVISIAE;

BIOTRANSFORMATION; ESCHERICHIA COLI; ESTERS; KETO ACIDS; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE;

EID: 0037664931     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9917036     Document Type: Note

References (28)

1. Mori, K. Tetrahedron 1989, 45, 3233-3298.
2. Pereira, R. Crit. Rev. Biotechnol. 1998, 18, 25-83.
3. Soai, K.; Yamanoi, T.; Hikima, H.; Oyamada, H. J. Chem. Soc., Chem. Commun. 1985, 138-139.
4. Noyori, R.; Ohkuma, T.; Kitamura, M. J. Am. Chem. Soc. 1987, 109, 5856-5858.
5. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134-9135.
6. Genêt, J. P.; Pinel, C.; Mallart, S.; Juge, S.; Thorimbert, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 555-567.
7. Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424.
8. Marcantoni, E.; Alessandrini, S.; Malavolta, M. J. Org. Chem. 1999, 64, 1986-1992.
9. Jones, J. B. In Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry; Trost, B. M., Flemming, I., Eds.; Pergamon Press: New York, 1991; Vol. 8, pp 183-209.
10. Csuk, R.; Glanzer, B. Chem. Rev. 1991, 91, 49-97.
11. Miya, H.; Kawada, M.; Sugiyama, Y. Biosci. Biotechnol. Biochem. 1996, 60, 95-98.
12. Shieh, W.-R.; Sih, C. J. Tetrahedron: Asymmetry 1993, 4, 1259-1269.
13. Nakamura, K.; Kawai, Y.; Nakajima, N.; Ohno, A. J. Org. Chem. 1991, 56, 4778-4783.
14. Zhou, B.; Gopalan, A. S.; VanMiddlesworth, F.; Shieh, W.-R.; Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925-5926.
15. Kawai, Y.; Kondo, S.; Tsujimoto, M.; Nakamura, K.; Ohno, A. Bull. Chem. Soc. Jpn. 1994, 67, 2244-2247.
16. D'Arrigo, P.; Pedrocchi-Fantoni, G.; Servi, S.; Strini, A. Tetrahedron: Asymmetry 1997, 8, 2375-2379.
17. Rodríguez, S.; Kayser, M.; Stewart, J. D. Org. Lett. 1999, 1, 1153-1155.
18. Sybesma, W. F. H.; Straathof, A. J. J.; Jongejan, J. A.; Pronk, J. T.; Heijnen, J. J. Biocat. Biotrans. 1998, 16, 95-134.
19. Stewart, J. D.; Rodríguez, S.; Kayser, M. M. In Enzyme Technologies for Pharmaceutical and Biotechnological Applications; Zmijewski, M. H, Kirst, H. A., Yeh, W.-K., Eds.; Marcel Dekker: New York, in press.
20. Kawai, Y.; Tsujimoto, M.; Kondo, S.; Takanobe, K.; Ohno, A.; Nakamura, K. Bull. Chem. Soc. Jpn. 1994, 67, 524-528.
21. Oechsner, U.; Magdolen, V.; Bandlow, W. FEBS Lett. 1988, 238, 123-128.
22. Kuhn, A.; van Zyl, C.; van Tonder, A.; Prior, B. A. Appl. Environ. Biotechnol. 1995, 61, 1580-1585.
23. Stecher, H.; Faber, K. Synthesis 1997, 1-16.
24. Fráter, G.; Müller, U.; Gunther, W. Tetrahedron 1984, 40, 1269-1277.
25. Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 3787-3793.
26. Harwood: L. M.; Moody, C. J. Experimental Organic Chemistry. Principles and Practice; 2nd ed.; Blackwell Scientific Publications: London, 1992.
27. LB (Luria-Bertani medium)-ampicillin: per liter, Bacto-Tryptone (10 g), Bacto-Yeast extract (5 g), NaCl (10 g), ampicillin (0.2 g; added after cooling), Bacto-Agar (15 g; included for solid media).
28. Centrifugation of the extraction mixture (4000 × g, 10 min) was useful to break the emulsions formed during some extractions.