Enzymes Catalyzing C-C Bond Formation for the Synthesis of Monosaccharide Analogs

Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions

Volumn , Issue , 2009, Pages 287-298

  Hecquet, Laurence ^a   Hélaine, Virgil ^a   Charmantray, Franck ^a   Lemaire, Marielle ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

C C bond formation; Chemoenzymatic synthesis; Monosaccharide analogs; Transketolase

Indexed keywords

EID: 84891032084     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527623839.ch18     Document Type: Chapter

References (50)

1. Machajewski, T.D. and Wong, C.H. (2000) Angewandte Chemie-International Edition, 39, 1352-1374.
2. Dean, S.M., Greenberg, W.A. and Wong, C.-H. (2007) Advanced Synthesis Catalysis, 349, 1308-1320 (and ref cited therein).
3. Samland, A.K. and Sprenger, G.A. (2006) Applied Microbiology and Biotechnology, 71, 253-264.
4. Wong, C.H., Mazenod, F.P. and Whitesides, G.M. (1983) The Journal of Organic Chemistry, 48, 3493-3497.
5. Straub, A., Effenberger, F. and Fischer, P. (1990) The Journal of Organic Chemistry, 55, 3926-3932.
6. Bednarski, M.D., Waldmann, H.J. and Whitesides, G.M. (1986) Tetrahedron Letters, 27, 5807-5810.
7. Bednarski, M.D., Simon, E.S., Bischofberger, N., Fessner, W.D., Kim, M.J., Lees, W., Saito, T., Waldmann, H. and Whitesides, G.M. (1989) Journal of the American Chemical Society, 111, 627-635.
8. Lemaire, M., Valentin, M.L., Hecquet, L., Demuynck, C. and Bolte, J. (1995) Tetrahedron: Asymmetry, 6, 67-70.
9. Andre, C., Guérard, C., Hecquet, L., Demuynck, C. and Bolte, J. (1998) Journal of Molecular Catalysis B: Enzymatic, 5, 459-466.
10. Crestia, D., Demuynck, C. and Bolte, J. (2004) Tetrahedron, 60, 2417-2425.
11. Schümperli, M., Pellaux, R. and Panke, S. (2007) Applied Microbiology and Biotechnology, 75, 33-45.
12. Ballou, C.E. and Fischer, H.O.L. (1956) Journal of the American Chemical Society, 78, 1659.
13. Valentin, M.-L. and Bolte, J. (1995) Bulletin de la Societe Chimique de France, 132, 1167-1171.
14. Gefflaut, T., Lemaire, M., Valentin, M.L. and Bolte, J. (1997) The Journal of Organic Chemistry, 62, 5920-5922.
15. Charmantray, F., El Blidi, L., Gefflaut, T., Hecquet, L., Bolte, J. and Lemaire, M. (2004) The Journal of Organic Chemistry, 69, 9310-9312.
16. Charmantray, F., Dellis, P., Samreth, S. and Hecquet, L. (2006) Tetrahedron Letters, 47, 3261-3263.
17. Bolte, J., Demuynck, C. and Samaki, H. (1987) Tetrahedron Letters, 27, 5525-5528.
18. Bolte, J., Demuynck, C., Hecquet, L. and Samaki, H. (1990) Carbohydrate Research, 206, 79-85.
19. Hecquet, L., Bolte, J. and Demuynck, C. (1993) Bioscience, Biotechnology, and Biochemistry, 57, 2174-2176.
20. Hecquet, L., Bolte, J. and Demuynck, C. (1996) Tetrahedron, 52, 8223-8232.
21. Morris, K.G., Smith, M.E.B. and Turner, N.J. (1996) Tetrahedron: Asymmetry, 7, 2185-2188.
22. Zimmermann, F.T., Schneider, A., Schörken, Y., Sprenger, G.A. and Fessner, W.D. (1999) Tetrahedron: Asymmetry, 10, 1643-1646.
23. Ziegler, T., Straub, A. and Effenberger, F. (1988) Angewandte Chemie-International Edition in English, 27, 716-721.
24. Kobori, Y., Myles, D.C. and Whitesides, G.M. (1991) The Journal of Organic Chemistry, 22, 5899-5907.
25. André, C., Guérard, C., Hecquet, L., Demuynck, C. and Bolte, J. (1998) Journal of Molecular Catalysis B: Enzymatic, 5, 459-466.
26. Guérard, C., Alphand, V., Archelas, A., Demuynck, C., Hecquet, L., Furstoss, R. and Bolte, J. (1999) European Journal of Organic Chemistry, 1, 3399-3402.
27. Crestia, D., Guérard, C., Veschambre, H., Hecquet, L., Demuynck, C. and Bolte, J. (2001) Tetrahedron: Asymmetry, 12, 869-876.
28. Charmantray, F., Dellis, P., Samreth, S. and Hecquet, L. (2006) European Journal of Organic Chemistry, 24, 5526-5532.
29. Sánchez-Moreno, I., García-García, J.F., Bastida, A. and García-Junceda, E. (2004) Chemical Communications, 14, 1634-1635.
30. Schoevaart, R., van Rantwijk, F. and Sheldon, R.A. (1999) Chemical Communications, 24, 2465-2466.
31. Schoevaart, R., van Rantwijk, F. and Sheldon, R.A. (2000) The Journal of Organic Chemistry, 65, 6940-6943.
32. Fessner, W.-D. and Sinerius, G. (1994) Angewandte Chemie-International Edition in English, 33, 209-212.
33. Krämer, L. and Steckhan, E. (1997) Tetrahedron, 53, 14645-14650.
34. El Blidi, L., Crestia, D., Gallienne, E., Demuynck, C., Bolte, J. and Lemaire, M. (2004) Tetrahedron: Asymmetry, 15, 2951-2954.
35. El Blidi, L., Ahbala, M., Bolte, J. and Lemaire, M. (2006) Tetrahedron Asymmetry, 17, 2684-2688.
36. Samreth, S., Barberousse, V., Bellamy, F., Horton, D., Masson, P., Millet, J., Renaut, P. and Sepulchre, C. (1994) Theveniaux. Actualites de Chimie Therapeutique, 21, 23-33.
37. Bellamy, F., Horton, D., Millet, J., Picard, F., Samreth, S. and Chazan, J.B. (1993) Journal of Medicinal Chemistry, 36, 898-903.
38. Paulsen, H. (1982) Angewandte Chemie-International Edition in English, 21, 155-173.
39. Schmidt, R.R. (1986) Angewandte Chemie-International Edition in English, 25, 212-235.
40. Kunz, H. (1987) Angewandte Chemie-International Edition in English, 26, 294-308.
41. Lalot, J., Stasik, I., Demailly, G. and Beaupère, D. (2003) Carbohydrate Research, 338, 2241-2245.
42. Durrwachter, J.R., Drueckhammer, D.G., Nozaki, K., Sweers, H.M. and Wong, C.-H. (1986) Journal of the American Chemical Society, 108, 7812-7818.
43. Chou, W.-C., Chen, L., Fang, J.-M. and Wong, C.-H. (1994) Journal of the American Chemical Society, 116, 6191-6194.
44. Fessner, W.-D., Gosse, C., Jaeschke, G. and Eyrisch, O. (2000) European Journal of Organic Chemistry, 1, 125-132.
45. Wikner, C., Meshalkina, L., Nilsson, U., Nikkola, M., Lindqvist, Y. and Schneider, G. (1994) The Journal of Biological Chemistry, 269, 32144-32150.
46. Nilsson, U., Hecquet, L., Gefflaut, T., Guérard, C. and Schneider, G. (1998) FEBS Letters, 424, 49-52.
47. Sevestre, A., Helaine, V., Guyot, G., Martin, C. and Hecquet, L. (2003) Tetrahedron Letters, 44, 827-830.
48. Klein, G. and Reymond, J.L. (1998) Bioorganic and Medicinal Chemistry Letters, 8, 1113-1116.
49. Jourdain, N., Carlon, R.P. and Reymond, J.L. (1998) Tetrahedron Letters, 39, 9415-9418.
50. Sevestre, A., Charmantray, F., Helaine, V., Lasikova, A. and Hecquet, L. (2006) Tetrahedron, 62, 3969-3976.