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40 hydrolysis, oxidation and reduction
6. A detailed review of the literature of non-enzymic catalysts is given in Comprehen-
sive Asymmetric Catalysis eds Jacobsen, E.N., Pfaltz, A. and Yamamoto, H.
Springer-Verlag, Berlin/Heidelberg, 1999. As an introductory text for post-graduate
students see Catalysis in Asymmetric Synthesis, Williams, J.M.J. Sheffield Academic
Press, Sheffield, UK, 1999. A comparison of biocatalysis versus chemical catalysis
has also been made by Averill, B.A., Laane, N.W.M., Straathof, A.J.J. and
Tramper, J., in Catalysis: An Integrated Approach (eds van Santen, R.A.; van
Leeuwen, P.W.N.M., Moulijn, J.A. and Averill, B.A.) Elsevier, The Netherlands,
1999, Chapter 7.
7. E ln[(1 ÿ c)(1 ÿ ee s )]=ln[(1 ÿ c)(1 ee s )] where c conversion (100 % 1.0);
ee s enantiomeric excess of substrate (100 % 1.0).
8. Ozaki, E. and Sakashita, K. Chem. Lett., 1997, 741.
9. Sakai, T., Miki, M., Nakatoni, M., Ema, T., Uneyama, K. and Utaka, M. Tetrahe-
dron Lett., 1998, 39 5233.
10. Models of lipases and esterases, Jones, L.E. and Kazlauskas, R. Tetrahedron:
Asymmetry, 1997, 8, 3719; references in Schmid, R.D. and Verger, R. Angew.
Chem. Int. Ed 1998, 37, 1609; Colombo, G., Toba, S. and Merz, K.M. J. Am.
Chem. Soc. 1999, 121, 3486.
11. Bakke, M., Takizawa, M., Sugai, T. and Ohta, H. J. Org. Chem. 1998, 63, 6929.
12. Guanti, G., Narisano, E. and Riva, R. Tetrahedron: Asymmetry, 1998, 9, 1859.
13. Bonini, C., Giugliano, A., Racioppi, R. and Righi, G. Tetrahedron Lett., 1996, 37
2487.
14. Hydrolases in Organic Synthesis by Bornscheuer, U.T. and Kazlauskas, R.J. Wiley-
VCH, Weinheim, 1999.
15. Luna, A., Astorga, C., Fu Èlo Èp, F. and Gotor, V. Tetrahedron: Asymmetry, 1998, 9,
4483.
16. Fujita, T., Tanaka, M., Norimine, Y., Suemune, H. and Sakai, K. J. Org. Chem.,
1997, 62, 3824.
17. Copeland, G.T., Jarvo, E.R. and Miller, S.J. J. Org. Chem., 1998, 63, 6784.
18. Oriyama, T., Imai, K., Hosoya, T. and Sano, T. Tetrahedron Lett., 1998, 39, 397.
19. Vedejs, E. and Daugulis, O. J. Am. Chem. Soc., 1999, 121, 5813; Tao, B., Ruble,
I.C., Hoic, D.A. and Fu, G.C. ibid, 1999, 121, 5091; Jarvo, E.R., Copeland, G.T.,
Papaioannou, N., Bonitatebus, P.J., Jr. and Miller, S.J. ibid, 1999, 121, 11638.
20. Effenberger, F., Graef, B.W. and Osswald, S. Tetrahedron Asymmetry, 1997, 8,
2749.
21. Taylor, S.J.C., Brown, R.C., Keene, P.A. and Taylor, I.N. Bioorg. Med. Chem.,
1999, 7, 2163.
22. Faber, K., Mischitz, M. and Kroutil, W. Acta Chem. Scand., 1996, 50, 249; Arche-
las, A. and Furstoss, R. Ann. Rev. Microbiol., 1997, 51, 491; see also C.A.G.M.
Weijers, Tetrahedron: Asymmetry, 1997, 8, 639.
23. Pedragosa-Moreau, S., Archelas, A. and Furstoss, R. Tetrahedron Lett., 1996, 37,
3319.
24. Pedragosa-Moreau, S., Archelas, A. and Furstoss, R. Tetrahedron, 1996, 52, 4593;
Pedragosa-Moreau, S., Morisseau, C., Zylber, J., Archelas, A., Baratti, J. and
Furstoss, R. J. Org. Chem., 1996, 61, 7402. A theoretical analysis of such epoxide
ring-opening reactions has been published, Moussou, P., Archelas, A., Baratti, J.
and Furstoss, R. Tetrahedron: Asymmetry, 1998, 9, 1539.
25. A review of the present position is available, Orru, R.V.A., Archelas, A., Furstoss,
R. and Faber, K. Adv. Biochem. Eng. Biotechnol. 1999, 63, 146; note that the
