Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11156-11157

  Zhao, Lishan ^a   Han, Bin ^a   Huang, Zilin ^a   Miller, Mark ^a   Huang, Hongjun ^a   Malashock, Dan S ^a   Zhu, Zuolin ^a   Milan, Aileen ^a   Robertson, Dan E ^a   Weiner, David P ^a   Burk, Mark J ^a  

^a DIVERSA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; EPOXIDE HYDROLASE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; HYDROLYSIS; PROTEIN EXPRESSION; SYNTHESIS;

ALCOHOLS; CATALYSIS; EPOXIDE HYDROLASES; EPOXY COMPOUNDS; STEREOISOMERISM;

EID: 4544314193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0466210     Document Type: Article

References (20)

1. Hannessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon Press: New York, 1983; Chapter 2.
2. For an alternative approach to the synthesis of optically active 1,2-diols, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
3. (a) Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776.
4. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252-2260.
5. For example, only two meso-epoxides were ring-opened at high ee and others were at <80% ee in the (salen)-Co-catalyzed addition of benzoic acid.
6. (a) Archelas, A.; Furstoss, R. Annu. Rev. Microbiol. 1997, 51, 491-525.
7. (b) Armstrong, R. N. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon Press: New York, 1999; Vol. 5, Chapter 4, pp 51-70.
8. Hydrolysis of several meso-epoxides by liver microsomes containing mammalian EH has been reported: (a) Bellucci, G.; Capitani, I.; Chiappe, C.; Marioni, F. J. Chem. Soc., Chem. Commun. 1989, 1170-1171.
9. (b) Bellucci, G.; Chiappe, C.; Marioni, F. J. Chem. Soc., Perkin Trans. 1 1989, 2369-2373.
10. (a) Faber, K.; Orru, R. V. A. In Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook; Drauz, K., Waldmann, H., Eds.; Wiley-VCH: Weinheim, 2002; Vol. II, p 592, and references therein.
11. (b) The only reported example using a bacterial epoxide hydrolase was the hydrolysis of cyclohexene oxide and N-benezyloxycarbonyl-3,4-epoxypyrrolidine: Chang, D.; Wang, Z.; Heringa, R. W.; Witholt, B.; Li, Z. Chem. Commun. 2003, 960-961. Whole cells were used, and the sequence and identity of the responsible EH were unknown.
12. (a) Robertson, D. E.; Mathur, M. J.; Swanson, R. V.; Marrs, B. L.; Short, J. M. SIM News 1996, 46, 3-8.
13. (b) Short, J. M. Nature Biotech. 1997, 15, 1322-1323.
14. (c) Henne, A.; Daniel, R.; Schmitz, R. A.; Gottschalk, G. Appl. Environ. Microbiol. 1999, 65, 3901-3907.
15. (d) Short, J. M. U.S. Patent 5,958,672, 1999.
16. For further details, see the Supporting Information.
17. The formed acyloxy intermediate is subsequently hydrolyzed by water to afford 1,2-diol product. Lacourciere, G. M.; Armstrong, R. N. J. Am. Chem. Soc. 1993, 115, 10466-10467.
18. (a) Rink, R.; Fennema, M.; Smids, M.; Dehmel, U.; Janssen, D. B. J. Biol. Chem. 1997, 272, 14650-14657.
19. (b) Morisseau, C.; Archelas, A.; Guitton, C.; Faucher, D.; Furstoss, R.; Baratti, J. C. Eur. J. Biochem. 1999, 263, 386-395.
20. Mammalian EH showed opposite enantioselectivity on several substrates with rigid tricyclic structures: Bellucci, G.; Berti, G.; Chiappe, C.; Fabri, F.; Marioni, F. J. Org. Chem. 1989, 54, 968-970.