Biocatalytic Asymmetric Oxidation for the Production of Bicyclic Proline Peptidomimetics

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions: Second Edition

Volumn , Issue , 2010, Pages 41-60

  Lalonde, James J ^a   Liang, Jack ^a  

^a Codexis Inc ^*  (United States)

Author keywords

Bicyclic proline peptidomimetics; Biocatalytic asymmetric oxidation; Boceprevir; Enzyme catalysis; Hepatitis C virus; Protease ketoamide inhibitor; Telaprevir

Indexed keywords

EID: 84885726478     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630639.ch4     Document Type: Chapter

References (33)

1. Njoroge, F.G., Chen, K.X., Shih, N.-Y., and Piwinski, J.J. (2008) Acc. Chem. Res., 41 (1), 50-59.
2. Love, R.A., Parge, H.E., Wichersham, J.A., Hostomsky, Z., Habuka, N., Moomaw, E.W., Adachi, T., and Hostomska, Z. (1996) Cell, 87, 331-342.
3. Trabocchi, A., Scarpi, D., and Guarna, A. (2008) Amino Acids, 34 (1), 1-24.
4. Zhang, R., Mamai, A., and Madalengoitia, J.S. (1999) J. Org. Chem., 64 (2), 547-555.
5. Baldwin, J.E., Moloney, M.G., and Bo Shim, S. (1991) Tetrahedron Lett., 32 (10), 1379-1380.
6. Garner, P. and Ramakanth, S.J. (1986) J. Org. Chem., 51, 2609.
7. Hendrata, S., Bennett, F., Huang, Y., Sannigrahi, M., Pinto, P.A., Chan, T.-M., Anderson Evans, C., Osterman, R., Buevich, A., and McPhail, A.T. (2006) Tetrahedron Lett., 47 (36), 6469-6472.
8. Park, J., Sudhakar, A., Tong, W., Vater, E.J., Wong, G.S., Chen, M., Weber, J., Yang, X., Kwok, D.-J., Jeon, I., Raghavan, R.R., and Tamarez, M. (2007) US Patent 7 309 717, to Schering Corp.
9. Nomura, Y., Ogawa, K., Takeuchi, Y., and Tomoda, S. (1977) Chem. Lett., 6 (6), 693-696.
10. Kollmeyer, W.D. (1980) US Patent 4 183 857, to Shell Oil Company, USA.
11. Henning, R., and Urbach, U. (1987) US Patent 4 691 022, to Hoechst AG.
12. Wu, G., Chen, F.X., Rashatasakhon, P., Eckert, J.M., Lee, H.-C., Erickson, N.C., Vance, J.A., Nichirio, P.C., Weber, J., Tsai, D.J.S., and Nanfei, Z. (2007) Patent WO 2007/075790, to Schering Corp.
13. Monn, J.A. and Valli, M.J. (1994) J. Org. Chem., 59 (10), 2773-2778.
14. Njoroge, F.G., Venkatraman, S., Arasappan, A., Velazquez, F., and Girijavallabhan, V. (2005) US Patent Application 2005/0197301, to Schering Corp.
15. Jao, E., Bogen, S., Saksena, A.K., and Girijavallabhan, V. (2003) Tetrahedron Lett., 44 (27), 5033-5035.
16. Tanoury, G.J., Chen, M., and Cochran, J.E. (2008) Patent WO 2007/022459, to Vertex Pharm, Inc.
17. Elkhatib, M., Peyrot, L., Scharff, J.P., and Delalu, H. (1998) Int. J. Chem. Kinet., 30 (2), 129-136.
18. Victorovna, A.M., Enright, A., Turner, N., John, and Mahmoudian, M. (2003) Patent WO 2003/080855, to Glaxo Group Ltd.
19. Liu, W., Laneman, S., Ager, D.J., and Taylor, P.P. (2002) US Patent 6 365 380, to P.C.B.U. Services.
20. Alexandre, F.-R., Pantaleone, D.P., Taylor, P.P., Fotheringham, I.G., Ager, D.J., and Turner, N.J. (2002) Tetrahedron Lett., 43 (4), 707-710.
21. Carr, R., Alexeeva, M., Enright, A., Eve, T.S., Dawson, M.J., and Turner, N.J. (2003) Angew. Chem. Int. Ed. Engl., 42 (39), 4807-4810.
22. Alexeeva, M., Enright, A., Dawson, M.J., Mahmoudian, M., and Turner, N. (2002) Angew. Chem. Int. Ed., 41, 3177.
23. Carr, R., Alexeeva, M., Dawson, M.J., Gotor-Fernandez, V., Humphrey, C.E., and Turner, N.J. (2005) ChemBioChem, 6, 637-639.
24. Dunsmore, C.J., Carr, R., Fleming, T., and Turner, N.J. (2006) J. Am. Chem. Soc., 128, 2224-2225.
25. Atkin, K.E., Reiss, R., Koehler, V., Bailey, K.R., Hart, S., Turkenburg, J.P., Turner, N.J., Brzozowski, A.M., and Grogan, G. (2008) J. Mol. Biol., 384 (5), 1218-1231.
26. Drauz, K. and Waldmann, H. (2002) Enzyme Catalysis in Organic Synthesis, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.
27. Liese, A., Seelbach, K., and Wandrey, C. (2006) Industrial Biotransformations, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.
28. Bommarius, A. and Bommarius-Riebel, B. (2005) Fundamentals of Biocatalysis, Wiley-VCH Verlag GmbH, Weinheim.
29. Fox, R.J. and Clay, M.D. (2009) Trends Biotechnol., 27 (3), 137-140.
30. Rothlisberger, D., Khersonsky, O., Wollacott, A.M., Jiang, L., DeChancie, J., Betker, J., Gallaher, J.L., Althoff, E.A., Zanghellini, A., Dym, O., Albeck, S., Houk, K.N., Tawfik, D.S., and Baker, D. (2008) Nature, 453 (7192), 190-195.
31. Luetz, S., Giver, L., and Lalonde, J. (2008) Biotechnol. Bioeng., 101 (4), 647-653.
32. Fox, R.J. and Huisman, G.W. (2008) Trends Biotechnol., 26 (3), 132-138.
33. Fox, R.J., Davis, S.C., Mundorff, E.C., Newman, L.M., Gavrilovic, V., Ma, S.K., Chung, L.M., Ching, C., Tam, S., Muley, S., Grate, J., Gruber, J., Whitman, J.C., Sheldon, R.A., and Huisman, G.W. (2007) Nat. Biotechnol., 25 (3), 338-344.