Enzyme-Catalyzed Asymmetric Synthesis: Kinetic Resolution of Racemic Hydroperoxides by Enantioselective Reduction to Alcohols with Horseradish Peroxidase

Journal of the American Chemical Society

Volumn 117, Issue 48, 1995, Pages 11898-11901

  Adam, Waldemar ^a   Saha Möller, Chantu R ^a   Hoch, Ute ^a   Lazarus, Michael ^a   Schreier, Peter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0029176375     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00153a010     Document Type: Article

References (39)

1. Ojima, I. Catalytic Asymmetric Synthesis; VCH Verlagsgesell-schaft: Weinheim, 1993.
2. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley Intescience Press: New York, 1994.
3. Johnson, R.A.; Sharpless, B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993, pp 103–158.
4. Jacobsen, E.N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993; pp 159—202.
5. Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.-S.; Kwong, H.L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768–2771.
6. Zhao, S.; Samuel, O.; Kagan, H.B. Org. Synth. 1989, 68, 49—56.
7. Zhao, S.; Samuel, O.; Kagan, H.B. Tetrahedron 1987, 43, 5135—5144.
8. Wong, C.H.; Whitesides, G.M. Enzymes in Synthetic Organic Chemistry: Pergamon: New York, 1994.
9. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Verlagsgesellschaft: New York/Weinheim, 1995.
10. Poppe, L.; Novak, L. Selective Biocatalysis; VCH Verlags-gesellschaft: Weinheim, 1992.
11. Dunford, H.B. In Peroxidases in Chemistry and Biology; Everse, J., Everse, K.E., Grisham. M.B., Eds.; CRC Press: Bota Raton, 1991; Vol. 2.
12. Fu, H.; Kondo, H.; Ichikawa, Y.; Look, G.C.; Wong, C.-H. J. Org. Chem. 1992, 57, 7265–7270.
13. Allain, E.J.; Hager, L.P.; Deng, L.; Jacobsen, E.N. J. Am Chem. Soc. 1993, 115, 4415–4416.
14. Dexter, A.F.; Lakner, F.J.; Cambell, R.A.; Hager, L.P. J. Am. Chem. Soc. 1995, 117, 6412–6413.
15. Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P. J. Chem. Soc., Chem. Commun. 1992, 357–358.
16. Harris, R.Z.; Newmeyer, S.L.; Ortiz de Montellano, P.R. J. Biol. Chem. 1993, 268, 1637–1645.
17. Ozaki, S.Y.; Ortiz de Montellano, P.R. J. Am. Chem. Soc. 1994, 116, 4487–4488.
18. Adam, W.; Hoch, U.; Saha-Moller, C.R.; Schreier, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1737–1739.
19. Hoft, E.; Hamann, H.-J.; Kunath, A.; Adam, W.; Hoch, U.; Saha-Moller, C.R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 603—608.
20. Adam, W.; Fell, T.R.; Hoch, U.; Saha-Moller, C.R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047–1050.
21. Dussault, P.; Porter, N.A. J. Am. Chem. Soc. 1988, 110, 6276—6277.
22. Dussault, P.; Lee, L.Q.; Kreifels, S. J. Org. Chem. 1991, 56, 4087–4089.
23. Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717—2720.
24. Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455–1460.
25. Hoft, E.; Haman, H.-J.; Kunath, A. J. Prakt. Chem. 1994, 336, 534–537.
26. Baba, N.; Mimura, M.; Hiratake, J.; Uchida, K.; Oda, J. Agric. Biol. Chem. 1988, 52, 2685–2687.
27. Shannon, L.M.; Kay, E.; Lew, J.Y. J. Biol. Chem. 1966, 241, 2166–2172.
28. Welinder, K.G. Eur. J. Biochem. 1985, 151, 497–504.
29. Ohlsson, P.J.; Paul, K.-G.; Wold, S. Acta Chem. Scand. 1984, B38, 853–859.
30. Marklud, S.; Ohlsson, P.J.; Opera, A.; Paul, K.G. Biochim. Biophys. Acta 1974, 350, 304—313.
31. Choudary, B.M.; Narender, N.; Bhuma, V. Synlett 1994, 641—642.
32. Matsushita, Y.; Matsui, T.; Sugamoto, K. Chem. Lett. 1992. 7, 1381–1384.
33. Burghardt, A. Chem. Stosow. 1988, 32, 523—533.
34. Sliwiok, J.; Ogierman, L. Microchem. J. 1979, 20, 547—552.
35. Davies, A.G.; Feld, F. J. Chem. Soc. 1956.
36. von Bussche-Hunnefeld, J.L.; Seebach, D. Tetrahedron 1992, 48, 5719—5730.
37. Jacquet, I.; Vigneron, J.P. Tetrahedron Lett. 1974, 24, 2065–2068.
38. Chance, B.; Maehly, A.C. Methods Enzymol. 1955, 2, 764—775.
39. Koch. R.B.; Stern, B.; Ferrari, C.G. Arch. Biochem. Biophys. 1958, 78, 165–179.