Improved biocatalysts from a synthetic circular permutation library of the flavin-dependent oxidoreductase old yellow enzyme

Journal of the American Chemical Society

Volumn 135, Issue 38, 2013, Pages 14425-14432

  Daugherty, Ashley B ^a   Govindarajan, Sridhar ^b   Lutz, Stefan ^a  

^a EMORY UNIVERSITY   (United States)

^b DNA20 ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC PERFORMANCE; CIRCULAR PERMUTATION; CONFORMATIONAL CHANGE; CONFORMATIONAL FLEXIBILITY; ENVIRONMENTAL CONDITIONS; FUNCTIONAL EVALUATION; SACCHAROMYCES PASTORIANUS; TRANS HYDROGENATIONS;

BIOCATALYSTS; CATALYST ACTIVITY; PROTEINS; SUBSTRATES;

ENZYMES;

CARVONE; CINNAMALDEHYDE; ISOPHORONE; KETOISOPHORONE; OXIDOREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE DEHYDROGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE DEHYDROGENASE 1; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; BIOCATALYST; CATALYSIS; CIRCULAR PERMUTATION; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME SUBSTRATE; EX VIVO STUDY; FUNGAL STRAIN; GENE EXPRESSION; GENE SEQUENCE; IN VITRO STUDY; NONHUMAN; NUCLEOTIDE SEQUENCE; PEPTIDE LIBRARY; PROTEIN ANALYSIS; PROTEIN ENGINEERING; PROTEIN FUNCTION; PROTEIN SYNTHESIS; SACCHAROMYCES PASTORIANUS; TRANSLATION INITIATION; WILD TYPE;

ACROLEIN; BACTERIAL PROTEINS; BIOCATALYSIS; CATALYTIC DOMAIN; CYCLOHEXANONES; KINETICS; MODELS, MOLECULAR; MONOTERPENES; NADPH DEHYDROGENASE; PROTEIN CONFORMATION; PROTEIN ENGINEERING; RECOMBINANT PROTEINS; SACCHAROMYCES; STEREOISOMERISM;

EID: 84884881164     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4074886     Document Type: Article

References (53)

1. Lu, S. M.; Bolm, C. Chemistry 2008, 14, 7513
2. Taylor, C. J. S. N.; Jaekel, C. Adv. Synth. Catal. 2008, 350, 2708
3. Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368
4. Tuttle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662
5. Bornscheuer, U. T.; Huisman, G. W.; Kazlauskas, R. J.; Lutz, S.; Moore, J. C.; Robins, K. Nature 2012, 485, 185
6. Nestl, B. M.; Nebel, B. A.; Hauer, B. Curr. Opin. Chem. Biol. 2011, 15, 187
7. Wohlgemuth, R. Curr. Opin. Biotechnol. 2010, 21, 713
8. Kawai, Y.; Inaba, Y.; Tokitoh, N. Tetrahedron: Asymmetry 2001, 12, 309
9. Kosjek, B.; Fleitz, F. J.; Dormer, P. G.; Kuethe, J. T.; Devine, P. N. Tetrahedron: Asymmetry 2008, 19, 1403
10. Hall, M.; Stueckler, C.; Hauer, B.; Stuermer, R.; Friedrich, T.; Breuer, M.; Kroutil, W.; Faber, K. Eur. J. Org. Chem. 2008, 9, 1511
11. Swiderska, M. A.; Stewart, J. D. J. Mol. Catal. B: Enzym. 2006, 42, 52
12. Adalbjornsson, B. V.; Toogood, H. S.; Fryszkowska, A.; Pudney, C. R.; Jowitt, T. A.; Leys, D.; Scrutton, N. S. ChemBioChem 2010, 11, 197
13. Toogood, H. S.; Fryszkowska, A.; Hare, V.; Fisher, K.; Roujeinikova, A.; Leys, D.; Gardiner, J. M.; Stephens, G. M.; Scrutton, N. S. Adv. Synth. Catal. 2008, 350, 2789
14. Toogood, H. S.; Gardiner, J. M.; Scrutton, N. S. ChemCatChem 2010, 2, 892
15. Stueckler, C.; Mueller, N. J.; Winkler, C. K.; Glueck, S. M.; Gruber, K.; Steinkellner, G.; Faber, K. Dalton Trans. 2010, 39, 8472
16. Hall, M.; Stueckler, C.; Ehammer, H.; Pointner, E.; Oberdorfer, G.; Gruber, K.; Hauer, B.; Stuermer, R.; Kroutil, W.; Macheroux, P.; Faber, K. Adv. Synth. Catal. 2008, 350, 411
17. Winkler, C. K.; Tasnadi, G.; Clay, D.; Hall, M.; Faber, K. J. Biotechnol. 2012, 162, 381
18. Schittmayer, M.; Glieder, A.; Uhl, M. K.; Winkler, A.; Zach, S.; Schrittwieser, J. H.; Kroutil, W.; Macheroux, P.; Gruber, K.; Kambourakis, S.; Rozzell, J. D.; Winkler, M. Adv. Synth. Catal. 2011, 353, 268
19. Pompeu, Y. A.; Sullivan, B.; Walton, A. Z.; Stewart, J. D. Adv. Synth. Catal. 2012, 354, 1949
20. Hulley, M. E.; Toogood, H. S.; Fryszkowska, A.; Mansell, D.; Stephens, G. M.; Gardiner, J. M.; Scrutton, N. S. ChemBioChem 2010, 11, 2433
21. Toogood, H. S.; Fryszkowska, A.; Hulley, M.; Sakuma, M.; Mansell, D.; Stephens, G. M.; Gardiner, J. M.; Scrutton, N. S. ChemBioChem 2011, 12, 738
22. Bougioukou, D. J.; Kille, S.; Taglieber, A.; Reetz, M. T. Adv. Synth. Catal. 2009, 351, 3287
23. Padhi, S. K.; Bougioukou, D. J.; Stewart, J. D. J. Am. Chem. Soc. 2009, 131, 3271
24. Hall, M.; Bommarius, A. S. Chem. Rev. 2011, 111, 4088
25. Reich, S.; Hoeffken, H. W.; Rosche, B.; Nestl, B. M.; Hauer, B. ChemBioChem 2012, 13, 2400
26. Brown, B. J.; Hyun, J. W.; Duvvuri, S.; Karplus, P. A.; Massey, V. J. Biol. Chem. 2002, 277, 2138
27. Vaz, A. D. N.; Chakraborty, S.; Massey, V. Biochemistry 1995, 34, 4246
28. Niino, Y. S.; Chakraborty, S.; Brown, B. J.; Massey, V. J. Biol. Chem. 1995, 270, 1983
29. Massey, V.; Schopfer, L. M. J. Biol. Chem. 1986, 261, 1215
30. Fox, K. M.; Karplus, P. A. Structure 1994, 2, 1089
31. Karplus, P. A.; Fox, K. M.; Massey, V. FASEB J. 1995, 9, 1518
32. Yu, Y.; Lutz, S. Trends Biotechnol. 2011, 29, 18
33. Qian, Z.; Lutz, S. J. Am. Chem. Soc. 2005, 127, 13466
34. Qian, Z.; Fields, C. J.; Lutz, S. ChemBioChem 2007, 8, 1989
35. Qian, Z.; Horton, J. R.; Cheng, X.; Lutz, S. J. Mol. Biol. 2009, 393, 191
36. Whitehead, T. A.; Bergeron, L. M.; Clark, D. S. Protein Eng. Des. Sel. 2009, 22, 607
37. Stephen, P.; Tseng, K. L.; Liu, Y. N.; Lyu, P. C. Chem. Commun. (Cambridge, U. K.) 2012, 48, 2612
38. Guntas, G.; Kanwar, M.; Ostermeier, M. PLoS One 2012, 7, e35998
39. Ueda, T.; Shimizu, Y.; Inoue, A.; Tomari, Y.; Suzuki, T.; Yokogawa, T.; Nishikawa, K. Nat. Biotechnol. 2001, 19, 751
40. Protein Generation Using a Reconstituted System. In Protein Engineering Handbook; Ying, B. W.; Ueda, T., Eds.; Wiley-VCH: Weinheim, Germany, 2009; Vol. 2.
41. Brown, B. J.; Deng, Z.; Karplus, P. A.; Massey, V. J. Biol. Chem. 1998, 273, 32753
42. Reitinger, S.; Yu, Y.; Wicki, J.; Ludwiczek, M.; D'Angelo, I.; Baturin, S.; Okon, M.; Strynadka, N. C.; Lutz, S.; Withers, S. G.; McIntosh, L. P. Biochemistry 2010, 49, 2464
43. Abramovitz, A. S.; Massey, V. J. Biol. Chem. 1976, 251, 5327
44. Stuermer, R.; Hauer, B.; Hall, M.; Faber, K. Curr. Opin. Chem. Biol. 2007, 11, 203
45. Wada, M.; Yoshizumi, A.; Noda, Y.; Kataoka, M.; Shimizu, S.; Takagi, H.; Nakamori, S. Appl. Environ. Microbiol. 2003, 69, 933
46. Kataoka, M.; Kotaka, A.; Hasegawa, A.; Wada, M.; Yoshizumi, A.; Nakamori, S.; Shimizu, S. Biosci., Biotechnol., Biochem. 2002, 66, 2651
47. Fryszkowska, A.; Toogood, H.; Sakuma, M.; Gardiner, J. M.; Stephens, G. M.; Scrutton, N. S. Adv. Synth. Catal. 2009, 351, 2976
48. Ay, J.; Hahn, M.; Decanniere, K.; Piotukh, K.; Borriss, R.; Heinemann, U. Proteins 1998, 30, 155
49. Chu, V.; Freitag, S.; Le Trong, I.; Stenkamp, R. E.; Stayton, P. S. Protein Sci. 1998, 7, 848
50. Manjasetty, B. A.; Hennecke, J.; Glockshuber, R.; Heinemann, U. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 304
51. Pieper, U.; Hayakawa, K.; Li, Z.; Herzberg, O. Biochemistry 1997, 36, 8767
52. Matthews, R. G.; Massey, V.; Sweeley, C. C. J. Biol. Chem. 1975, 250, 9294
53. van den Heuvel, R. H.; van den Berg, W. A.; Rovida, S.; van Berkel, W. J. J. Biol. Chem. 2004, 279, 33492