Substrate specificity in thiamin diphosphate-dependent decarboxylases

Bioorganic Chemistry

Volumn 43, Issue , 2012, Pages 26-36

  Andrews, Forest H ^a   McLeish, Michael J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Benzoylformate; Carboligation; Mutagenesis; Pyruvate; Thiamin diphosphate

Indexed keywords

2 KETO ACID DECARBOXYLASE; 2 OXOACID; BENZOYLFORMATE DECARBOXYLASE; CARBOXYLYASE; INDOLEPYRUVATE DECARBOXYLASE; OXALYL COA DECARBOXYLASE; PHENYLPYRUVATE DECARBOXYLASE; PYRUVATE DECARBOXYLASE; THIAMIN DIPHOSPHATE; THIAMIN DIPHOSPHATE DEPENDENT DECARBOXYLASE; THIAMINE; THIAMINE PHOSPHATE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; AZOSPIRILLUM BRASILENSE; CHEMICAL BOND; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME STRUCTURE; HUMAN; HYDROGEN BOND; MOLECULAR INTERACTION; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN MOTIF; PROTON TRANSPORT; PSEUDOMONAS PUTIDA; SACCHAROMYCES CEREVISIAE; SCREENING; SEQUENCE ALIGNMENT; ZYMOMONAS MOBILIS;

EID: 84864403459     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2011.12.001     Document Type: Review

References (77)

1. M. Pohl, G.A. Sprenger, and M. Müller Curr. Opin. Biotechnol. 15 2004 335 342
2. R. Kluger, and K. Tittmann Chem. Rev. 108 2008 1797 1833
3. A. Kaplun, E. Binshtein, M. Vyazmensky, A. Steinmetz, Z. Barak, D.M. Chipman, K. Tittmann, and B. Shaanan Nat. Chem. Biol. 4 2008 113 118
4. F. Guo, D. Zhang, A. Kahyaoglu, R.S. Farid, and F. Jordan Biochemistry 37 1998 13379 13391
5. R.G. Duggleby Acc. Chem. Res. 39 2006 550 557
6. A. Schellenberger Angew. Chem., Int. Ed. 6 1967 1024 1035
7. R. Kluger Mechanisms of enzymic carbon-carbon bond formation and cleavage D.S. Sigman, The Enzymes vol. 20 1992 Academic Press San Diego 271 315
8. M. Knoll, M. Muller, J. Pleiss, and M. Pohl Chembiochem 7 2006 1928 1934
9. S. Kutter, M.S. Weiss, G. Wille, R. Golbik, M. Spinka, and S. Konig J. Biol. Chem. 284 2009 12136 12144
10. X.Y. Pei, K.M. Erixon, B.F. Luisi, and F.J. Leeper Biochemistry 49 2010 1727 1736
11. S. Kutter, G. Wille, S. Relle, M.S. Weiss, G. Hubner, and S. Konig FEBS J. 273 2006 4199 4209
12. A. Schütz, T. Sandalova, S. Ricagno, G. Hubner, S. Konig, and G. Schneider Eur. J. Biochem. 270 2003 2312 2321
13. A. Schütz, R. Golbik, S. Konig, G. Hübner, and K. Tittmann Biochemistry 44 2005 6164 6179
14. C.L. Berthold, D. Gocke, M.D. Wood, F.J. Leeper, M. Pohl, and G. Schneider Acta Crystallogr. D. Biol. Crystallogr. 63 2007 1217 1224
15. W. Versées, S. Spaepen, J. Vanderleyden, and J. Steyaert FEBS J. 274 2007 2363 2375
16. D. Meyer, P. Neumann, C. Parthier, R. Friedemann, N. Nemeria, F. Jordan, and K. Tittmann Biochemistry 49 2010 8197 8212
17. W. Versées, S. Spaepen, M.D. Wood, F.J. Leeper, J. Vanderleyden, and J. Steyaert J. Biol. Chem. 282 2007 35269 35278
18. M. Liu, E.A. Sergienko, F. Guo, J. Wang, K. Tittmann, G. Hubner, W. Furey, and F. Jordan Biochemistry 40 2001 7355 7368
19. E.A. Sergienko, and F. Jordan Biochemistry 40 2001 7369 7381
20. M. Pohl, P. Siegert, K. Mesch, H. Bruhn, and J. Grotzinger Eur. J. Biochem. 257 1998 538 546
21. A.K. Chang, P.F. Nixon, and R.G. Duggleby Biochem. J. 339 1999 255 260
22. Y.G. Wu, A.K. Chang, P.F. Nixon, W. Li, and R.G. Duggleby Eur. J. Biochem. 267 2000 6493 6500
23. C.Y. Huang, A.K. Chang, P.F. Nixon, and R.G. Duggleby Eur. J. Biochem. 268 2001 3558 3565
24. M.M. Kneen, R. Stan, A. Yep, R.P. Tyler, C. Saehuan, and M.J. McLeish FEBS J. 278 2011 1842 1853
25. G. Lu, D. Dobritzsch, S. Baumann, G. Schneider, and S. Konig Eur. J. Biochem. 267 2000 861 868
26. S. Bringer-Meyer, K.L. Schimz, and H. Sahm Arch. Microbiol. 146 1986 105 110
27. D. Gocke, T. Graf, H. Brosi, I. Frindi-Wosch, L. Walter, M. Müller, and M. Pohl J. Mol. Catal. B 61 2009 30 35
28. J.A. Vaccaro, E.J. Crane 3rd, T.K. Harris, and M.W. Washabaugh Biochemistry 34 1995 12636 12644
29. S. Spaepen, W. Versees, D. Gocke, M. Pohl, J. Steyaert, and J. Vanderleyden J. Bacteriol. 189 2007 7626 7633
30. H. Iding, P. Siegert, K. Mesch, and M. Pohl Biochim. et Biophys. Acta 1385 1998 307 322
31. H. Bruhn, M. Pohl, J. Grotzinger, and M.-R. Kula Eur. J. Biochem. 234 1995 650 655
32. G.D. Hegeman Meth. Enzymol. 17A 1970 674 678
33. D.N.R. Rao, and C.S. Vaidyanathan Can. J. Microbiol. 23 1977 1496 1499
34. C.A. Fewson FEMS Microbiol. Rev. 4 1988 85 110
35. C. Saehuan, T. Rojanarata, S. Wiyakrutta, M.J. McLeish, and V. Meevootisom Biochim. et Biophys. Acta 1770 2007 1585 1592
36. M.S. Hasson, A. Muscate, M.J. McLeish, L.S. Polovnikova, J.A. Gerlt, G.L. Kenyon, G.A. Petsko, and D. Ringe Biochemistry 37 1998 9918 9930
37. E.S. Polovnikova, M.J. McLeish, E.A. Sergienko, J.T. Burgner, N.L. Anderson, A.K. Bera, F. Jordan, G.L. Kenyon, and M.S. Hasson Biochemistry 42 2003 1820 1830
38. S. Chakraborty, N.S. Nemeria, A. Balakrishnan, G.S. Brandt, M.M. Kneen, A. Yep, M.J. McLeish, G.L. Kenyon, G.A. Petsko, D. Ringe, and F. Jordan Biochemistry 48 2009 981 994
39. G.S. Brandt, M.M. Kneen, S. Chakraborty, A.T. Baykal, N. Nemeria, A. Yep, D.I. Ruby, G. Petsko, G.L. Kenyon, M.J. McLeish, F. Jordan, and D. Ringe Biochemistry 48 2009 3247 3257
40. E.A. Sergienko, J. Wang, L. Polovnikova, M.S. Hasson, M.J. McLeish, G.L. Kenyon, and F. Jordan Biochemistry 39 2000 13862 13869
41. M. Bruning, M. Berheide, D. Meyer, R. Golbik, H. Bartunik, A. Liese, and K. Tittmann Biochemistry 48 2009 3258 3268
42. A. Yep, and M.J. McLeish Biochemistry 48 2009 8387 8395
43. P. Siegert, M.J. McLeish, M. Baumann, H. Iding, M.M. Kneen, G.L. Kenyon, and M. Pohl Prot. Eng. Des. Sel. 18 2005 345 357
44. M. Pohl, D. Gocke, L. Walter, E. Gauchenova, G. Kolter, M. Knoll, C.L. Berthold, G. Schneider, J. Pleiss, and M. Müller Chembiochem 9 2008 406 412
45. A.K. Bera, L.S. Polovnikova, J. Roestamadji, T.S. Widlanski, G.L. Kenyon, M.J. McLeish, and M.S. Hasson J. Am. Chem. Soc. 129 2007 4120 4121
46. M. Widmann, R. Radloff, and J. Pleiss BMC Biochem. 11 2010 9
47. A.L. Baetz, and M.J. Allison J. Bacteriol. 171 1989 2605 2608
48. C.L. Berthold, P. Moussatche, N.G. Richards, and Y. Lindqvist J. Biol. Chem. 280 2005 41645 41654
49. T. Werther, A. Zimmer, G. Wille, R. Golbik, M.S. Weiss, and S. Konig FEBS J. 277 2010 2628 2640
50. X. Zeng, B. Farrenkopf, S. Hohmann, F. Dyda, W. Furey, and F. Jordan Biochemistry 32 1993 2704 2709
51. C.L. Berthold, C.G. Toyota, P. Moussatche, M.D. Wood, F. Leeper, N.G. Richards, and Y. Lindqvist Structure 15 2007 853 861
52. A.K. Chang, P.F. Nixon, and R.G. Duggleby Biochemistry 39 2000 9430 9437
53. C. Fuganti, and P. Grasselli J. Chem. Soc. Chem. Comm. 4 1982 205 206
54. D. Gala, D.J. DiBenedetto, J.E. Clark, B.L. Murphy, D.P. Schumacher, and M. Steinman Tetrahedron Lett. 37 1996 611 614
55. C. Neuberg, and H. Ohle Biochem. Z. 128 1922 610 615
56. G. Hildebrandt, W. Klavehn, Verfahren zur Herstellung von 1-1-Phenyl-2-Methylaminopropan-1-ol., German Patent 548 459, 1932.
57. M. Pohl, B. Lingen, and M. Müller Chemistry 8 2002 5288 5295
58. O.P. Ward, and A. Singh Enzyme biotransformation involving α-ketoacid decarboxylases E. Mellado, J.-L. Barredo, Microorganisms for Industrial Enzymes and Biocontrol 2005 Research Signpost Trivandrum, India 83 94
59. D. Gocke, C.L. Nguyen, M. Pohl, T. Stillger, L. Walter, and M. Müller Adv. Synth. Catal. 349 2007 1425 1435
60. D. Meyer, L. Walter, G. Kolter, M. Pohl, M. Müller, and K. Tittmann J. Am. Chem. Soc. 133 2011 3609 3616
61. A. Baykal, S. Chakraborty, A. Dodoo, and F. Jordan Bioorg. Chem. 34 2006 380 393
62. A. Yep, G.L. Kenyon, and M.J. McLeish Bioorg. Chem. 34 2006 325 336
63. R. Wilcocks, and O.P. Ward Biotechnol. Bioeng. 39 1992 1058 1063
64. R. Wilcocks, O.P. Ward, S. Collins, N.J. Dewdney, Y. Hong, and E. Prosen Appl. Environ. Microbiol. 58 1992 1699 1704
65. A.S. Demir, P. Ayhan, and S.B. Sopaci Water 35 2007 406 412
66. D. Gocke, L. Walter, E. Gauchenova, G. Kolter, M. Knoll, C.L. Berthold, G. Schneider, J. Pleiss, M. Müller, and M. Pohl Chembiochem 9 2008 406 412
67. A.S. Demir, T. Dünnwald, H. Iding, M. Pohl, and M. Müller Tetrahdron: Asymmetry 10 1999 4769 4774
68. D. Rother, G. Kolter, T. Gerhards, C.L. Berthold, E. Gauchenova, M. Knoll, J. Pleiss, M. Müller, G. Schneider, and M. Pohl ChemCatChem 3 2011 1587 1596
69. T. Dünnwald, A.S. Demir, P. Siegert, M. Pohl, and M. Müller Eur. J. Org. Chem. 2000 2161 2170
70. H. Iding, T. Dünnwald, L. Greiner, A. Liese, M. Müller, P. Siegert, J. Grötzinger, A.S. Demir, and M. Pohl Chem. Eur. J. 6 2000 1483 1495
71. B. Lingen, J. Grotzinger, D. Kolter, M.R. Kula, and M. Pohl Protein Eng. 15 2002 585 593
72. B. Lingen, D. Kolter-Jung, P. Dunkelmann, R. Feldmann, J. Grotzinger, M. Pohl, and M. Muller Chembiochem 4 2003 721 726
73. P. Dünkelmann, D. Kolter-Jung, A. Nitsche, A.S. Demir, P. Siegert, B. Lingen, M. Baumann, M. Pohl, and M. Müller J. Am. Chem. Soc. 124 2002 12084 12085
74. A. Steinmetz, M. Vyazmensky, D. Meyer, Z.E. Barak, R. Golbik, D.M. Chipman, and K. Tittmann Biochemistry 49 2010 5188 5199
75. H. Li, and F. Jordan Biochemistry 38 1999 10004 10012
76. A. Schütz, R. Golbik, K. Tittmann, D.I. Svergun, M.H. Koch, G. Hübner, and S. Konig Eur. J. Biochem. 270 2003 2322 2331
77. The PyMOL Molecular Graphics System, Schrödinger, LLC.