Conversion of pyruvate decarboxylase into an enantioselective carboligase with biosynthetic potential

Journal of the American Chemical Society

Volumn 133, Issue 10, 2011, Pages 3609-3616

  Meyer, Danilo ^a,b   Walter, Lydia ^c   Kolter, Geraldine ^d   Pohl, Martina ^d   Müller, Michael ^c   Tittmann, Kai ^a,b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c UNIVERSITY OF FREIBURG   (Germany)

^d FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; ASYMMETRIC SYNTHESIS; CARBOLIGATION; COFACTORS; ENANTIOSELECTIVE; ENANTIOSELECTIVE FORMATION; PROTEIN VARIANTS; PYRUVATE DECARBOXYLASE; PYRUVATES; RATIONAL DESIGN; REACTIVE INTERMEDIATE; SIDE REACTIONS; SUBSTRATE SPECIFICITY; THIAMIN DIPHOSPHATE;

ALDEHYDES; CARBOXYLATION; CATALYSIS; ENZYMES; KETONES; METHANOL; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

REACTION INTERMEDIATES;

ALDEHYDE; ENAMINE; KETONE; PYRUVATE DECARBOXYLASE;

ARTICLE; BIOCATALYSIS; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; CIRCULAR DICHROISM; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; GENE EXPRESSION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN PURIFICATION; STEADY STATE; THERMOSTABILITY;

AMINO ACID SUBSTITUTION; CATALYSIS; CATALYTIC DOMAIN; ENZYME STABILITY; GLUTAMIC ACID; GLUTAMINE; METHANOL; PYRUVATE DECARBOXYLASE; SUBSTRATE SPECIFICITY;

EID: 79952603240     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110236w     Document Type: Article

References (34)

1. Kazlauskas, R. J. Curr. Opin. Chem. Biol. 2005, 9, 195-201
2. Hult, K.; Berglund, P. Trends Biotechnol. 2007, 25, 231-238
3. Khersonsky, O.; Tawfik, D. S. Annu. Rev. Biochem. 2010, 79, 471-505.
4. Chen, R. D. Trends Biotechnol. 2001, 19, 13-14
5. Penning, T. M.; Jez, J. M. Chem. Rev. 2001, 101, 3027-3046
6. Aharoni, A.; Gaidukov, L.; Khersonsky, O.; Gould, S. M.; Roodveldt, C.; Tawfik, D. S. Nat. Genet. 2005, 37, 73-76
7. Candy, J. M.; Duggleby, R. G. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1998, 1385, 323-338
8. Kluger, R.; Tittmann, K. Chem. Rev. 2008, 108, 1797-1833
9. Chang, A. K.; Nixon, P. F.; Duggleby, R. G. Biochem. J. 1999, 339, 255-260
10. Sergienko, E. A.; Jordan, F. Biochemistry 2001, 40, 7369-7381
11. Nemeria, N.; Tittmann, K.; Joseph, E.; Zhou, L.; Vazquez-Coll, M. B.; Arjunan, P.; Hübner, G.; Furey, W.; Jordan, F. J. Biol. Chem. 2005, 280, 21473-21482
12. Fang, Q. K.; Han, Z. X.; Grover, P.; Kessler, D.; Senanayake, C. H.; Wald, S. A. Tetrahedron: Asymmetry 2000, 11, 3659-3663
13. Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.; Kobayashi, K.; Osada, H. J. Org. Chem. 1999, 64, 1052-1053
14. Stermitz, F. R.; Tawara-Matsuda, J.; Lorenz, P.; Mueller, P.; Zenewicz, L.; Lewis, K. J. Nat. Prod. 2000, 63, 1146-1149
15. Hildebrandt, G.; Klavehn, W. Dtsch. Reichspatent 1932, 548, 459
16. Shukla, V. B.; Kulkarni, P. R. World J. Microbiol. Biotechnol. 2000, 16, 499-506
17. Rosche, B.; Sandford, V.; Breuer, M.; Hauer, B.; Rogers, P. L. J. Mol. Catal. B: Enzym. 2002, 19, 109-115
18. Müller, M.; Gocke, D.; Pohl, M. FEBS J. 2009, 276, 2894-2904
19. Oliver, A. L.; Anderson, B. N.; Roddick, F. A. Adv. Microb. Physiol. 1999, 41, 1-45.
20. Sandford, V.; Breuer, M.; Hauer, B.; Rogers, P.; Rosche, B. Biotechnol. Bioeng. 2005, 91, 190-198
21. Gunawan, C.; Satianegara, G.; Chen, A. K.; Breuer, M.; Hauer, B.; Rogers, P. L.; Rosche, B. FEMS Yeast Res. 2007, 7, 33-39
22. Bruhn, H.; Pohl, M.; Grotzinger, J.; Kula, M. R. Eur. J. Biochem. 1995, 234, 650-655
23. Tittmann, K.; Golbik, R.; Uhlemann, K.; Khailova, L.; Schneider, G.; Patel, M.; Jordan, F.; Chipman, D. M.; Duggleby, R. G.; Hübner, G. Biochemistry 2003, 42, 7885-7891
24. Meyer, D.; Neumann, P.; Parthier, C.; Friedemann, R.; Nemeria, N.; Jordan, F.; Tittmann, K. Biochemistry 2010, 49, 8197-8212
25. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254
26. Gocke, D.; Walter, L.; Gauchenova, E.; Kolter, G.; Knoll, M.; Berthold, C. L.; Schneider, G.; Pleiss, J.; Müller, M.; Pohl, M. ChemBioChem 2008, 9, 406-412
27. Abell, L. M.; Schloss, J. V. Biochemistry 1991, 30, 7883-7887
28. Breuer, M.; Pohl, M.; Hauer, B.; Lingen, B. Anal. Bioanal.Chem. 2002, 374, 1069-1073
29. Steinmetz, A.; Vyazmensky, M.; Meyer, D.; Barak, Z.; Golbik, R.; Chipman, D. M.; Tittmann, K. Biochemistry 2010, 49, 5188-5199
30. Tokuriki, N.; Stricher, F.; Serrano, L.; Tawfik, D. S. PLoS Comput. Biol. 2008, 4, e1000002
31. Jackel, C.; Kast, P.; Hilvert, D. Annu. Rev. Biophys. 2008, 37, 153-173
32. Reetz, M. T.; Carballeira, J. D. Nat. Protoc. 2007, 2, 891-903
33. Baykal, A.; Chakraborty, S.; Dodoo, A.; Jordan, F. Bioorg. Chem. 2006, 34, 380-93
34. Wille, G.; Meyer, D.; Steinmetz, A.; Hinze, E.; Golbik, R.; Tittmann, K. Nat. Chem. Biol. 2006, 2, 324-328