Dihydroxyacetone Phosphate-Dependent Aldolases in the Core of Multi-Step Processes

Multi-Step Enzyme Catalysis: Biotransformations and Chemoenzymatic Synthesis

Volumn , Issue , 2008, Pages 61-81

  Iturrate, Laura ^a   García Junceda, Eduardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Aldol reaction; Asymmetric synthesis; Dihydroxyacetone phosphate; Dihydroxyacetone phosphate dependent aldolases; Multi step processes; Stereochemistry

Indexed keywords

EID: 84889396624     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527623389.ch4     Document Type: Chapter

References (91)

1. Corey, E.J. and Cheng, X.M. (1989) The Logic of Chemical Synthesis, John Wiley & Sons, Ltd, New York.
2. Li, C.J. (2005) Chemical Reviews, 105, 3095-166.
3. Palomo, C., Oiarbide, M. and García, J.M. (2004) Chemical Society Reviews, 33, 65-75.
4. Alcaide, B. and Almendros, P. (2003) Angewandte Chemie (International Edition in English), 42, 858-60.
5. Sukumaran, J. and Hanefeld, U. (2005) Chemical Society Reviews, 34, 530-42.
6. Rutter, W.J. (1964) Federation Proceedings, 23, 1248-57.
7. Horecker, B.L., Tsolas, O. and Lai, C.-Y. (1972) The Enzymes, 3rd edn, VII (ed. P.D. Boyer), Academic Press, New York, pp. 213-58.
8. Samland, A.K. and Sprenger, G.A. (2006) Applied Microbiology and Biotechnology, 71, 253-64.
9. Hamilton, C.J. (2004) Natural Product Reports, 21, 365-85.
10. Breuer, M. and Hauer, B. (2003) Current Opinion in Biotechnology, 14, 570-6.
11. Silvestri, M.G., Desantis, G., Mitchell, M. and Wong, C.-H. (2003) Topics in Stereochemistry (ed. E.D. Scott), Wiley-VCH, Weinheim, Vol. 23, pp. 267-342.
12. Fessner, W.-D. and Helaine, V. (2001) Current Opinion in Biotechnology, 12, 574-86.
13. Machajewski, T.D. and Wong, C.-H. (2000) Angewandte Chemie (International Edition in English), 39, 1352-74.
14. Wymer, N. and Toone, E.J. (2000) Current Opinion in Chemical Biology, 4, 110-19.
15. Seoane, G. (2000) Current Organic Chemistry, 4, 283-304.
16. Liu, J.Q., Dairi, T., Itoh, N., Kataoka, M., Shimizu, S. and Yamada, H. (2000) Journal of Molecular Catalysis B: Enzymatic, 10, 107-15.
17. Fessner, W.-D., Sinerius, G., Schneider, A., Dreyer, M., Schulz, G.E., Badia, J. and Aguilar, J. (1991) Angewandte Chemie (International Edition in English), 30, 555-8.
18. Lin, C.H., Sugai, T., Halcomb, R.L., Ichikawa, Y. and Wong, C.H. (1992) Journal of the American Chemical Society, 114, 10138-45.
19. Espelt, L., Parella, T., Bujons, J., Solans, C., Joglar, J., Delgado, A. and Clapés, P. (2003) Chemistry-A European Journal, 9, 4887-99.
20. Fessner, W.-D. and Eyrisch, O. (1992) Angewandte Chemie (International Edition in English), 31, 56-8.
21. Williams, G.J., Domann, S., Nelson, A. and Berry, A. (2003) Proceedings of the National Academy of Sciences of the United States of America, 100, 3143-8.
22. Drueckhammer, D.G., Durrwachter, J.R., Pederson, R.L., Crans, D.C., Daniels, L. and Wong, C.-H. (1989) Journal of Organic Chemistry, 54, 70-7.
23. Schoevaart, R., van Rantwijk, F. and Sheldon, R.A. (2001) Journal of Organic Chemistry, 66, 4559-62.
24. Sugiyama, M., Hong, Z., Whalen, L.J., Greenberg, W.A. and Wong, C.-H. (2006) Advanced Synthesis Catalysis, 348, 2555-9.
25. Sugiyama, M., Hong, Z., Greenberg, W.A. and Wong, C.-H. (2007) Bioorganic and Medicinal Chemistry, 15, 5905-11.
26. Jung, S.H., Jeong, J.-H., Miller, P. and Wong, C.-H. (1994) Journal of Organic Chemistry, 59, 7182-4.
27. Charmantray, F., El Blidi, L., Gefflaut, T., Hecquet, L., Bolte, J. and Lemaire, M. (2004) Journal of Organic Chemistry, 69, 9310-12.
28. Gefflaut, T., Lemaire, M., Valentin, M.-L. and Bolte, J. (1997) Journal of Organic Chemistry, 62, 5920-2.
29. Fessner, W.-D. and Sinerius, G. (1994) Angewandte Chemie (International Edition in English), 33, 209-12.
30. Schoevaart, R., van Rantwijk, F. and Sheldon, R.A. (1999) Chemical Communications, 2465-6.
31. Schoevaart, R., van Rantwijk, F. and Sheldon, R.A. (2000) Journal of Organic Chemistry, 65, 6940-3.
32. Charmantray, F., Dellis, P., Samreth, S. and Hecquet, L. (2006) Tetrahedron Letters, 47, 3261-3.
33. van Herk, T., Hartog, A.F., Schoemaker, H.E. and Wever, R. (2006) Journal of Organic Chemistry, 71, 6244-7.
34. Wong, C.-H. and Whitesides, G.M. (1983) Journal of Organic Chemistry, 48, 3199-205.
35. Zhao, H. and van der Donk, W.A. (2003) Current Opinion in Biotechnology, 14, 583-9.
36. Endo, T. and Koizumi, S. (2001) Advanced Synthesis Catalysis, 343, 521-6.
37. Shiba, T., Tsutsumi, K., Ishige, K. and Noguchi, T. (2000) Biochemistry (Moscow), 65, 315-23.
38. Murata, K., Uchida, T., Kato, J. and Chibata, I. (1988) Agricultural and Biological Chemistry, 52, 1471-7.
39. Noguchi, T. and Shiba, T. (1998) Bioscience, Biotechnology, and Biochemistry, 62, 1594-6.
40. Erni, B., Siebold, C., Christen, S., Srinivas, A., Oberholzer, A. and Baumann, U. (2006) Cellular and Molecular Life Sciences, 63, 890-900.
41. Itoh, N., Tujibata, Y. and Liu, J.Q. (1999) Applied Microbiology and Biotechnology, 51, 193-200.
42. Sánchez-Moreno, I., García-García, J.F., Bastida, A. and García-Junceda, E. (2004) Chemical Communications, 1634-5.
43. Crans, D.C. and Whitesides, G.M. (1983) Journal of Organic Chemistry, 48, 3130-2.
44. Schümperli, M., Pellaux, R. and Panke, S. (2007) Applied Microbiology and Biotechnology, 75, 33-45.
45. Withers, S.G., Namchuk, M. and Mosi, R. (1999) Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (ed. A.E. Stütz), Wiley-VCH, Weinheim, pp. 188-206.
46. Lillelund, V.H., Jensen, H.H., Liang, X. and Bols, M. (2002) Chemical Reviews, 102, 515-53.
47. Compain, P. and Martin, O.R. (2003) Current Topics in Medicinal Chemistry, 3, 541-60.
48. Look, G.C., Fotsch, C.H. and Wong, C.-H. (1993) Accounts of Chemical Research, 26, 182-90.
49. Whalen, L.J. and Wong, C.-H. (2006) Aldrichimica Acta, 39, 63-71.
50. 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, 3924-7.
51. Pederson, R.L. and Wong, C.-H. (1989) Heterocycles, 28, 477-80.
52. Hung, R.R., Straub, J.A. and Whitesides, G.M. (1991) Journal of Organic Chemistry, 56, 3849-55.
53. Romero, A. and Wong, C.-H. (2000) Journal of Organic Chemistry, 65, 8264-8.
54. Espelt, L., Clapés, P., Esquena, J., Manich, A. and Solans, C. (2003) Langmuir, 19, 1337-46.
55. Espelt, L., Bujons, J., Parella, T., Calveras, J., Joglar, J., Delgado, A. and Clapés, P. (2005) Chemistry-A European Journal, 11, 1392-401.
56. Calveras, J., Bujons, J., Parella, T., Crehuet, R., Espelt, L., Joglar, J. and Clapés, P. (2006) Tetrahedron, 62, 2648-56.
57. Card, P.J. and Hitz, W.D. (1985) Journal of Organic Chemistry, 50, 891-3.
58. Kajimoto, T., Liu, K.K.-C., Pederson, R.L., Zhong, Z., Ichikawa, Y., Porco, J.A., Jr and Wong, C.-H. (1991) Journal of the American Chemical Society, 113, 6187-96.
59. Kajimoto, T., Chen, L., Liu, K.K.-C. and Wong, C.-H. (1991) Journal of the American Chemical Society, 113, 6678-80.
60. Qian, X.-H., Morís-Varas, F., Fitzgerald, M.C. and Wong, C.-H. (1996) Bioorganic and Medicinal Chemistry, 4, 2055-69.
61. Qian, X.-H, Morís-Varas, F. and Wong, C.-H. (1996) Bioorganic and Medicinal Chemistry Letters, 6, 1117-22.
62. Morís-Varas, F., Qian, X.-H. and Wong, C.-H. (1996) Journal of the American Chemical Society, 118, 7647-52.
63. El Blidi, L., Crestia, D., Gallienne, E., Demuynck, C., Bolte, J. and Lemaire, M. (2004) Tetrahedron: Asymmetry, 15, 2951-4.
64. El Blidi, L., Ahbala, M., Bolte, J. and Lemaire, M. (2006) Tetrahedron: Asymmetry, 17, 2684-8.
65. Fessner, W.-D., Badia, J., Eyrisch, O., Schneider, A. and Sinerius, G. (1992) Tetrahedron Letters, 33, 5231-4.
66. Fessner, W.-D., Schneider, A., Eyrisch, O., Sinerius, G. and Badia, J. (1993) Tetrahedron: Asymmetry, 4, 1183-92.
67. Alajarin, R., Garcia-Junceda, E. and Wong, C.-H. (1995) Journal of Organic Chemistry, 60, 4294-5.
68. Franke, D., Machajewski, T., Hsu, C.-C. and Wong, C.-H. (2003) Journal of Organic Chemistry, 68, 6828-31.
69. Durrwachter, J.R., Sweers, H.M., Nozaki, K. and Wong, C.-H. (1986) Tetrahedron Letters, 27, 1261-4.
70. Durrwachter, J.R., Drueckhammer, D.G., Nozaki, K., Sweers, H.M. and Wong, C.-H. (1986) Journal of the American Chemical Society, 108, 7812-18.
71. Wong, C.-H., Alajarin, R., Moris-Varas, F., Blanco, O. and García-Junceda, E. (1995) Journal of Organic Chemistry, 60, 7360-3.
72. Fessner, W.-D., Gosse, C., Jaeschke, G. and Eyrisch, O. (2000) European Journal of Organic Chemistry, 125-32.
73. Schultz, M., Waldmann, H., Kunz, H. and Vogt, W. (1990) Liebigs Annalen der Chemie, 1019-24.
74. Schultz, M., Waldmann, H., Vogt, W. and Kunz, H. (1990) Tetrahedron Letters, 31, 867-8.
75. Maliakel, B.P. and Schmid, W. (1992) Tetrahedron Letters, 33, 3297-300.
76. Maliakel, B.P. and Schmid, W. (1993) Journal of Carbohydrate Chemistry, 12, 415-24.
77. Phung, A.N., Zannetti, M.T., Whited, G. and Fessner, W.-D. (2003) Angewandte Chemie (International Edition in English), 42, 4821-4.
78. Gabrielsen, B., Monath, T.P., Huggins, J.W., Kefauver, D.F., Pettit, G.R., Groszek, G., Hollingshead, M., Kirsi, J.J., Shannon, W.M. and Schubert, E.M. (1992) Journal of Natural Products, 55, 1569-81.
79. Hoshino, O. (1998) The Alkaloids (ed. G.A. Cordell), Academic Press, New York, Vol. 51, pp. 324-424.
80. Ouarzane-Amara, M., Franetich, J.-F., Mazier, D., Pettit, G.R., Meijer, L., Doerig, C. and Desportes-Livage, I. (2001) Antimicrobial Agents and Chemotherapy, 45, 3409-15.
81. Fessner, W.-D. and Walter, C. (1996) Topics in Current Chemistry, 184, 97-194.
82. Fessner, W.-D. (2000) Stereoselective Biocatalysis (ed. R.N. Patel), Marcel Dekker, New York, pp. 239-65.
83. Shimagaki, M., Muneshima, H., Kubota, M. and Oishi, T. (1993) Chemical & Pharmaceutical Bulletin, 41, 282-6.
84. Chênevert, R., Lavoie, M. and Dasser, M. (1997) Canadian Journal of Chemistry-Revue Canadienne de Chimie, 75, 68-73.
85. Malleron, A. and David, S. (1996) New Journal of Chemistry, 20, 153-9.
86. Midland, S.L., Keen, N.T., Sims, J.J., Midland, M.M., Stayton, M.M., Burton, V., Smith, M.J., Mazzola, E.P., Graham, K.J. and Clardy, J. (1993) Journal of Organic Chemistry, 58, 2940-5.
87. Chênevert, R. and Dasser, M. (2000) Journal of Organic Chemistry, 65, 4529-31.
88. Schürmann, M. and Sprenger, G.A. (2001) Journal of Biological Chemistry, 276, 11055-61.
89. Schürmann, M., Schürmann, M. and Sprenger, G.A. (2002) Journal of Molecular Catalysis B: Enzymatic, 19-20, 247-52.
90. 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, 14811-17.
91. Castillo, J.A., Calveras, J., Casas, J., Mitjans, M., Vinardell, M.P., Parella, T., Inoue, T., Sprenger, G.A., Joglar, J. and Clapes, P. (2006) Organic Letters, 8, 6067-70.