Synthetic potential of thiamin diphosphate-dependent enzymes

Journal of Molecular Catalysis - B Enzymatic

Volumn 6, Issue 3, 1999, Pages 145-159

  Sprenger, Georg A ^a   Pohl, Martina ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

hydroxyketones; 1 deoxyxylulose 5 phosphate; Acyloin condensations; Benzoylformate decarboxylase; Phenylacetyl carbinol; Pyruvate decarboxylase; Site directed mutagenesis; Thiamin diphosphate; Transketolase

Indexed keywords

BIOTECHNOLOGY; KETONES; METABOLITES; MUTAGENESIS; PHOSPHATES; SYNTHESIS (CHEMICAL); VITAMINS;

THIAMIN DIPHOSPHATES;

ENZYMES;

BREVICOMIN; COCARBOXYLASE; EPHEDRINE; GLYCOSIDASE INHIBITOR; ISOPRENOID; PHENYLGLYOXYLIC ACID; PYRUVATE DECARBOXYLASE; SEX PHEROMONE; THIAMINE PHOSPHATE; TRANSKETOLASE;

BIOTRANSFORMATION; CATALYST; CHEMICAL REACTION; ENZYME SUBSTRATE; ENZYME SYNTHESIS; REVIEW; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY;

EID: 0033545539     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(98)00107-6     Document Type: Review

References (88)

1. Toone E.J., Simon E.S., Whitesides G.M. Tetrahedron Lett. 45:1989;5365.
2. D.G. Drueckhammer, W.J. Hennen, R.L. Pederson, C.F. Barbas, C.M. Gautheron, T. Krach, C.H. Wong, Synthesis (1991) 499.
3. K. Faber, Biotransformations in Organic Chemistry, Springer-Verlag, Berlin, 1992, p. 204.
4. C.H. Wong, G.M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994, p. 195.
5. Wong C.H., Halcomb R.L., Ichikawa Y., Kajimoto T. Angew. Chem. 107:1995;453.
6. Gijsen H.J.M., Qiao L., Fitz W., Wong C.H. Chem. Rev. 96:1996;443.
7. Fessner W.-D., Walter C. Top. Curr. Chem. 184:1996;97.
8. Takayama S., McGarvey G.J., Wong C.H. Annu. Rev. Microbiol. 51:1997;285.
9. K. Drauz, H. Waldmann (Eds.), Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, Germany, 1996.
10. Kluger R. Enzymes. 10:1992;271.
11. Csuk R., Glänzer B.I. Chem. Rev. 91:1991;49.
12. Krampitz L.O. Annu. Rev. Biochem. 38:1969;213.
13. Crout D.H.G., Davies S., Heath R.J., Miles C.O., Rathbone R., Swoboda B.E.P., Gravestone M.B. Biocatalysis. 9:1994;1.
14. U. Schörken, G.A. Sprenger, Biochim. Biophys. Acta (1998) in press.
15. H. Iding, P. Siegert, K. Mesch, M. Pohl, Biochim. Biophys. Acta (1998) in press.
16. G. Hildebrandt, W. Klavehn, German patent 548 459, 1932.
17. Bringer-Meyer S., Sahm H. Biocatalysis. 1:1988;321.
18. D.H.G. Crout, H. Dalton, D.W. Hutchinson, M. Miyagoshi, J. Chem. Soc. Perkin Trans. I (1991) 1329.
19. Sprenger G.A., Schörken U., Sprenger G., Sahm H. Eur. J. Biochem. 230:1995;525.
20. Effenberger F., Null V., Ziegler T. Tetrahedron Lett. 33:1992;5157.
21. F. Effenberger, A. Straub, V. Null, Liebigs Ann. Chem., 1992, p. 1297.
22. Kobori Y., Myles D.C., Whitesides G.M. J. Org. Chem. 57:1992;5899.
23. Demuynck C., Bolte J., Hecquet L., Dalmas V. Tetrahedron Lett. 32:1991;5085.
24. G.R. Hobbs, M.D. Lilly, N.J. Turner, J.M. Ward, A.J. Willets, J.M. Woodley, J. Chem. Soc. Perkin Trans. I (1993) 165.
25. Morris K.G., Smith E.B., Turner N.J., Lilly M.D., Mitra R.K., Woodley J.M. Tetrahedron Asymmetry. 7:1996;2185.
26. U. Schörken, H. Sahm, G.A. Sprenger, Biochemistry and physiology of thiamin diphosphate enzymes, in: H. Bisswanger, A. Schellenberger (Eds.), A&C Intemann Verlag, Prien, Germany, 1996, p. 543.
27. Baden D.G., Corbett M.D., Chipko B.R. Bioorg. Chem. 9:1980;231.
28. Villafranca J.J., Axelrodt B. J. Biol. Chem. 246:1971;3126.
29. Dickens F., Williamson D.H. Nature. 181:1958;1790.
30. Datta A.G., Racker E. J. Biol. Chem. 236:1961;617.
31. Josephson B.L., Fraenkel D.G. J. Bacteriol. 100:1969;1289.
32. Bolte J., Demuynck C., Samaki H. Tetrahedron Lett. 28:1987;5525.
33. Demuynck C., Bolte J., Hecquet L., Samaki H. Carbohydr. Res. 206:1990;79.
34. Myles D.C., Andrulis P.J. III, Whitesides G.M. Tetrahedron Lett. 32:1991;4835.
35. Ziegler T., Straub A., Effenberger F. Angew. Chem. 100:1988;737.
36. F. Effenberger, V. Null, Liebigs Ann. Chem. (1992) 1211.
37. Hecquet L., Lemaire M., Bolte J., Demuynck C. Tetrahedron Lett. 35:1994;8791.
38. Yanase H., Okuda M., Kita K., Sato Y., Shibata K., Sakai Y., Kato N. Appl. Microbiol. Biotechnol. 43:1995;228.
39. Rohmer M., Knani M., Simonin P., Sutter B., Sahm H. Biochem. J. 295:1993;517.
40. Rohmer M., Seemann M., Horbach S., Bringer-Meyer S., Sahm H. J. Am. Chem. Soc. 118:1996;2564.
41. Arigoni D., Sagner S., Latzel C., Eisenreich W., Bacher A., Zenk M.H. Proc. Natl. Acad. Sci. U.S.A. 94:1997;10600.
42. Sprenger G.A., Schörken U., Wiegert T., Grolle S., de Graaf A.A., Taylor S.V., Begley T.P., Bringer-Meyer S., Sahm H. Proc. Natl. Acad. Sci. U.S.A. 94:1997;12857.
43. T.P. Begley, Nat. Prod. Rep. (1996) 177.
44. Spenser I.D., White R.L. Angew. Chem. Int. Ed. Engl. 36:1997;1032.
45. Taylor S.V., Vu L.D., Begley T.P., Schörken U., Sprenger G.A., Bringer-Meyer S., Sahm H. J. Org. Chem. 63:1998;2375-2377.
46. Backstrom A.D., McMordie R.A.S., Begley T.P. J. Carbohydr. Chem. 14:1995;171-175.
47. Piel J., Boland W. Tetrahedron Lett. 38:1997;6387.
48. Yokota A., Sasajima K.-I. Agric. Biol. Chem. 50:1986;2517.
49. Yokota A., Sasajima K.-I. Agric. Biol. Chem. 48:1984;149.
50. Yokota A., Sasajima K.-I. Agric. Biol. Chem. 48:1984;1643.
51. Pohl M. Adv. Biochem. Eng. Biotechnol. 58:1997;16.
52. Dyda F., Furey W., Swaminathan S., Sax M., Farrenkopf B.C., Jordan F. Biochemistry. 32:1993;6165.
53. Arjunan P., Umland T., Dyda F., Swaminathan S., Furey W., Sax M., Farrenkopf B., Gao Y., Zhang D., Jordan F. J. Mol. Biol. 256:1996;590.
54. Lu G., Dobritzsch D., König S., Schneider G. FEBS Lett. 403:1997;249.
55. Hegeman G.D. Methods Enzymol. 17:1970;674.
56. Barrowman M.M., Harnett W., Scott A.J., Fewson C.A., Kusel J.R. FEMS Microbiol. Lett. 34:1986;57.
57. Barrowman M.M., Fewson C.A. Curr. Microbiol. 12:1985;235.
58. Tsou A.Y., Ransom S.C., Gerlt J.A., Buechter D.D., Babbitt P.C., Kenyon G.L. Biochemistry. 29:1990;9856.
59. Hasson M.S., Muscate A., Henehan G.T.M., Guidinger P.F., Petsko G.A., Ringe D., Kenyon G.L. Protein Sci. 4:1995;955.
60. M.S. Hasson, A. Muscate, G.L. Kenyon, G.A. Petsko, D. Ringe, Biochemistry and physiology of thiamin diphosphate enzymes, in: H. Bisswanger, A. Schellenberger (Eds.), A&C Intemann Verlag, Prien, Germany, 1996, p. 174.
61. Reynolds L.J., Garcia G.A., Kozarich J.W., Kenyon G.L. Biochemistry. 27:1988;5530.
62. Weiss P.M., Garcia G.A., Kenyon G.L., Cleland W.W., Cook P.F. Biochemistry. 27:1988;2197.
63. Wilcocks R., Ward O.P. Biotechnol. Bioeng. 39:1992;1058.
64. Wilcocks R., Ward O.P., Collins S., Dewdney N.J., Hong Y., Prosen E. Appl. Environ. Microbiol. 58:1992;1699.
65. Prosen E., Ward O.P. J. Ind. Microbiol. 13:1994;287.
66. Kluger R. Chem. Rev. 87:1987;863.
67. Kern D., Kern G., Neef H., Tittmann K., Killenberg-Jabs M., Wikner C., Schneider G., Hübner G. Science. 275:1997;67.
68. Kuo D.J., Jordan F. J. Biol. Chem. 225:1983;13415.
69. Zeng X., Chung A., Haran M., Jordan F. J. Am. Chem. Soc. 113:1991;5842.
70. Menon-Rudolph S., Nishikawa S., Zeng X., Jordan F. J. Am. Chem. Soc. 114:1992;10110.
71. Dirmaier L.J., Garcia G.A., Kozarich J.W., Kenyon G.L. J. Am. Chem. Soc. 108:1986;3149.
72. Schellenberger A. Angew. Chem. 79:1967;1050.
73. Chen G.C., Jordan F. Biochemistry. 23:1984;3582.
74. Shin H.S., Rogers P.L. Biotechnol. Bioeng. 49:1996;52.
75. M. Pohl, K. Mesch, H. Bruhn, G. Goetz, H. Iding, M.R. Kula, Biochemistry and physiology of thiamin diphosphate enzymes, in: H. Bisswanger, A. Schellenberger (Eds.), A&C Intemann Verlag, Prien, Germany, 1996, p. 151.
76. Bruhn H., Pohl M., Grötzinger J., Kula M.R. Eur. J. Biochem. 234:1995;650.
77. H. Bruhn, M. Pohl, K. Mesch, M.R. Kula, German patent 195 23 269, 1995, pp. 0-41.
78. Chow Y.S., Shin H.S., Adesina A.A., Rogers P.L. Biotechnol. Lett. 17:1995;1201.
79. Singer T.P., Pensky J. Arch. Biochem. Biophys. 31:1951;457.
80. Singer T.P., Pensky J. Biochim. Biophys. Acta. 9:1952;316.
81. S. Bornemann, D.H.G. Crout, H. Dalton, D.W. Hutchinson, G. Dean, N. Thomson, M.M. Turner, J. Chem. Soc. Perkin Trans. I (1993) 309.
82. D.H.G. Crout, J. Littlechild, S.M. Morrey, J. Chem. Soc. Perkin Trans. I, 1986, p. 105.
83. S. Bornemann, D.H.G. Crout, H. Dalton, V. Kren, M.Lobell, G. Dean, N. Thomson, M.M. Turner, J. Chem. Soc. Perkin Trans. I (1996) 425.
84. Lobell M., Crout D.H.G. J. Am. Chem. Soc. 118:1996;1867.
85. Lindqvist Y., Schneider G., Ermler U., Sundström M. EMBO J. 11:1992;2373.
86. Nilsson U., Meshalkina L., Lindqvist Y., Schneider G. J. Biol. Chem. 272:1997;1864.
87. Wikner C., Meshalkina L., Nilsson U., Bäckström S., Lindqvist Y., Schneider G. Eur. J. Biochem. 233:1995;750.
88. Y. Lindqvist, L. Meshalkina, U. Nilsson, G. Schneider, C. Wikner, Biochemistry and physiology of thiamin diphosphate enzymes, in: H. Bisswanger, A. Schellenberger (Eds.), A&C Intemann Verlag, Prien, Germany, 1996, p. 505.