Novel Strategies in Aldolase-Catalyzed Synthesis of Iminosugars

Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions

Volumn , Issue , 2009, Pages 299-311

  Clapés, Pere ^a   Sprenger, Georg A ^b   Joglar, Jesús ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Aldolase catalyzed synthesis; D fructose 1,6 diphosphate aldolase from rabbit muscle; Glycosidases; Glycosyltransferases; Iminosugars

Indexed keywords

EID: 84886028660     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527623839.ch19     Document Type: Chapter

References (73)

1. Koeller, K.M. and Wong, C.H. (2000) Nature Biotechnology, 18, 835-841.
2. Asano, N. (2000) Journal of Enzyme Inhibition, 15, 215-234.
3. Asano, N. (2003) Glycobiology, 13, 93R-104R.
4. Wong, C.-H. (ed.) (2003) Carbohydrate-Based Drug Discovery, Vol. 1, 2, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
5. Fiaux, H., Popowycz, F., Favre, S., Schutz, C., Vogel, P., Gerber-Lemaire, S. and Juillerat-Jeanneret, L. (2005) Journal of Medicinal Chemistry, 48, 4237-4246.
6. Kolter, T. and Wendeler, M. (2003) Chembiochem, 4, 260-264.
7. Asano, N., Nash, R.J., Molyneux, R.J. and Fleet, G.W.J. (2000) Tetrahedron: Asymmetry, 11, 1645-1680.
8. Compain, P. and Martin, O.R. (2001) Bioorganic and Medicinal Chemistry, 9, 3077-3092.
9. Watson, A.A., Fleet, G.W.J., Asano, N., Molyneux, R.J. and Nash, R.J. (2001) Phytochemistry, 56, 265-295.
10. Butters, T.D., Dwek, R.A. and Platt, F.M. (2003) Current Topics in Medicinal Chemistry, 3, 561-574.
11. Heightman, T.D. and Vasella, A.T. (1999) Angewandte Chemie-International Edition, 38, 750-770.
12. Vasella, A., Davies, G.J. and Bohm, M. (2002) Current Opinion in Chemical Biology, 6, 619-629.
13. Cipolla, L., La Ferla, B. and Gregori, M. (2006) Combinatorial Chemistry and High Throughput Screening, 9, 571-582.
14. Wrodnigg, T.M. and Sprenger, F.K. (2004) Mini Reviews in Medicinal Chemistry, 4, 437-459.
15. Ayad, T., Genisson, Y. and Baltas, M. (2004) Current Organic Chemistry, 8, 1211-33.
16. Cipolla, L., La Ferla, B. and Nicotra F. (2003) Current Topics in Medicinal Chemistry, 3, 485-511.
17. Whalen, L.J. and Wong, C.H. (2006) Aldrichimica Acta, 39, 63-71.
18. Kato, A., Kato, N., Kano, E., Adachi, I., Ikeda, K., Yu, L., Okamoto, T., Banba, Y., Ouchi, H., Takahata, H. and Asano, N. (2005) Journal of Medicinal Chemistry, 48, 2036-2044.
19. Ouchi, H., Mihara, Y., Watanabe, H. and Takahata, H. (2004) Tetrahedron Letters, 45, 7053-7056.
20. Asano, N., Ikeda, K., Yu, L., Kato, A., Takebayashi, K., Adachi, I., Kato, I., Ouchi, H., Takahata, H. and Fleet, G.W.J. (2005) Tetrahedron: Asymmetry, 16, 223-229.
21. Takahata, H., Banba, Y., Ouchi, H., Nemoto, H., Kato, A. and Adachi, I. (2003) The Journal of Organic Chemistry, 68, 3603-3607.
22. Fessner, W.D. (2007) Asymmetric Synthesis with Chemical and Biological Methods (eds D. Enders and K.-E. Jaeger), Wiley-VCH Verlag GmbH & Co KGaA, Weinheim, pp. 351-375.
23. Dean, S.M., Greenberg, W.A. and Wong, C.-H. (2007) Advanced Synthesis Catalysis, 349, 1308-1320.
24. Samland, A.K. and Sprenger, G.A. (2006) Applied Microbiology and Biotechnology, 71, 253-264.
25. Hung, R.R., Straub, J.A. and Whitesides, G.M. (1991) The Journal of Organic Chemistry, 56, 3849-3855.
26. Look, G.C., Fotsch, C.H. and Wong, C.H. (1993) Accounts of Chemical Research, 26, 182-190.
27. Bräse, S., Gil, C., Knepper, K. and Zimmermann, V. (2005) Angewandte Chemie-International Edition, 44, 5188-5240.
28. Jurczak, J. and Golebiowski, A. (1989) Chemical Reviews, 89, 149-164.
29. Jurczak, J., Gryko, D., Kobrzycka, E., Gruza, H. and Prokopowicz, P. (1998) Tetrahedron, 54, 6051-6064.
30. Von der Osten, C.H., Sinskey, A.J., Barbas, C.F. III, Pederson, R.L., Wang, Y.F. and Wong, C.H. (1989) Journal of the American Chemical Society, 111, 3924-3927.
31. Romero, A. and Wong, C.H. (2000) The Journal of Organic Chemistry, 65, 8264-8268.
32. Pederson, R.L. and Wong, C.H. (1989) Heterocycles, 28, 477-480.
33. Azema, L., Bringaud, F., Blonski, C. and Perie, J. (2000) Bioorganic and Medicinal Chemistry, 8, 717-722.
34. Sobolov, S.B., Bartoszko-Malik, A., Oeschger, T.R. and Montelbano, M.M. (1994) Tetrahedron Letters, 35, 7751-7754.
35. Clapés, P., Espelt, L., Navarro, M.A. and Solans, C. (2001) Journal of the Chemical Society. Perkin Transactions, 2, 1394-1399.
36. Espelt, L., Clapes, P., Esquena, J., Manich, A. and Solans, C. (2003) Langmuir, 19, 1337-1346.
37. Ostwald, W. (1910) Wilmersdorf Z Chem Ind Kolloide, 8, 103-109.
38. Lissant, K.J. (1966) Journal of Colloid and Interface Science, 22, 462-468.
39. Princen, H.M. (1979) Journal of Colloid and Interface Science, 71, 55-66.
40. Solans, C., Pons, R. and Kuniedain, H. (1998) in Modern Aspects of Emulsion Science (eds B.P. Binks), The Royal Society of Chemistry, Cambridge, U.K, pp. 367-394.
41. Espelt, L., Bujons, J., Parella, T., Calveras, J., Joglar, J., Delgado, A. and Clapés, P. (2005) Chemistry-A European Journal, 11, 1392-1401.
42. Espelt, L., Parella, T., Bujons, J., Solans, C., Joglar, J., Delgado, A. and Clapés, P. (2003) Chemistry-A European Journal, 9, 4887-4899.
43. Fessner, W.D., Sinerius, G., Schneider, A., Dreyer, M., Schulz, G.E., Badia, J. and Aguilar, J. (1991) Angewandte Chemie, 103, 596-599.
44. Gefflaut, T., Blonski, C., Perie, J. and Willson, M. (1995) Progress in Biophysics and Molecular Biology, 63, 301-340.
45. Fessner, W.-D., Schneider, A., Held, H., Sinerius, G., Walter, C., Hixon, M. and Schloss, J.V. (1996) Angewandte Chemie-International Edition, 35, 2219-2221.
46. Dalby, A., Dauter, Z. and Littlechild, J.A. (1999) Protein Science, 8, 291-297.
47. Hall, D.R., Leonard, G.A., Reed, C.D., Watt, C.I., Berry, A. and Hunter, W.N. (1999) Journal of Molecular Biology, 287, 383-394.
48. Fessner, W.-D. and Walter, C. (1996) Topics in Current Chemistry, 184, 97-194.
49. Wong, C.-H., Alajarin, R., Moris-Varas, F., Blanco, O. and Garcia-Junceda, E. (1995) The Journal of Organic Chemistry, 60, 7360-7363.
50. Mitchell, M., Qaio, L. and Wong, C.H. (2001) Advanced Synthesis Catalysis, 343, 596-599.
51. Joerger, A.C., Gosse, C., Fessner, W.-D. and Schulz, G.E. (2000) Biochemistry, 39, 6033-6041.
52. Waldmann, H. and Reidel, A. (1997) Angewandte Chemie-International Edition, 36, 647-649.
53. Kajimoto, T., Chen, L., Liu, K.K.C. and Wong, C.H. (1991) Journal of the American Chemical Society, 113, 6678-6680.
54. Liu, K.K.C., Kajimoto, T., Chen, L., Zhong, Z., Ichikawa, Y. and Wong, C.H. (1991) The Journal of Organic Chemistry, 56, 6280-6289.
55. Takayama, S., Martin, R., Wu, J., Laslo, K., Siuzdak, G. and Wong, C.-H. (1997) Journal of the American Chemical Society, 119, 8146-8151.
56. Calveras, J., Casas, J., Parella, T., Joglar, J. and Clapés, P. (2007) Advanced Synthesis Catalysis, 349, 1661-1666.
57. Asano, N., Kuroi, H., Ikeda, K., Kizu, H., Kameda, Y., Kato, A., Adachi, I., Watson, A.A., Nash, R.J. and Fleet, G.W.J. (2000) Tetrahedron: Asymmetry, 11, 1-8.
58. Jung, S.-H., Jeong, J.-H., Miller, P. and Wong, C.-H. (1994) The Journal of Organic Chemistry, 59, 7182-7184.
59. Gefflaut, T., Lemaire, M., Valentin, M.-L. and Bolte, J. (1997) The Journal of Organic Chemistry, 62, 5920-5922.
60. Ferroni, E.L., Ditella, V., Ghanayem, N., Jeske, R., Jodlowski, C., Oconnell, M., Styrsky, J., Svoboda, R., Venkataraman, A. and Winkler, B.M. (1999) The Journal of Organic Chemistry, 64, 4943-4945.
61. Charmantray, F., El Blidi, L., Gefflaut, T., Hecquet, L., Bolte, J. and Lemaire, M. (2004) The Journal of Organic Chemistry, 69, 9310-9312.
62. Meyer, O., Ponaire, S., Rohmer, M. and Grosdemange-Billiard, C. (2006) Organic Letters, 8, 4347-4350.
63. Fessner, W.D. and Sinerius, G. (1994) Angewandte Chemie-International Edition, 33, 209-212.
64. Sanchez-Moreno, I., Francisco Garcia-Garcia, J., Bastida, A. and Garcia-Junceda, E. (2004) Chemical Communications, 1634-1635.
65. van Herk, T., Hartog, A.F., Schoemaker, H.E. and Wever, R. (2006) The Journal of Organic Chemistry, 71, 6244-6247.
66. Sugiyama, M., Hong, Z.Y., Whalen, L.J., Greenberg, W.A. and Wong, C.H. (2006) Advanced Synthesis Catalysis, 348, 2555-2559.
67. Sugiyama, M., Hong, Z., Greenberg, W.A. and Wong, C.-H. (2007) Bioorganic and Medicinal Chemistry, 15, 5905-5911.
68. Schürmann, M. and Sprenger, G.A. (2001) The Journal of Biological Chemistry, 276, 11055-11061.
69. Schürmann, M., Schürmann, M. and Sprenger, G.A. (2002) Journal of Molecular Catalysis B: Enzymatic, 19, 247-252.
70. Castillo, J.A., Calveras, J., Casas, J., Mitjans, M., Vinardell, M.P., Parella, T., Inoue, T., Sprenger, G.A., Joglar, J. and Clapés, P. (2006) Organic Letters, 8, 6067-6070.
71. Koyama, M. and Sakamura, S. (1974) Agricultural and Biological Chemistry, 38, 1111-1112.
72. Sugiyama, M., Hong, Z., Liang, P.H., Dean, S.M., Whalen, L.J., Greenberg, W.A. and Wong, C.H. (2007) Journal of the American Chemical Society, 129, 14811-14817.
73. Sprenger, G.A., Schürmann, M., Schürmann, M., Johnen, S., Sprenger, G., Sahm, H., Inoue, T. and Schörken, U. (2007) Asymmetric Synthesis with Chemical and Biological Methods (eds D. Enders and K.-E. Jaeger), Wiley-VCH Verlag GmbH & Co KGaA, Weinheim, pp. 312-326.