The nature of chemical innovation: New enzymes by evolution

Quarterly Reviews of Biophysics

Volumn 48, Issue 4, 2015, Pages 404-410

  Arnold, Frances H ^a  

^a California Institute of Technology   (United States)

Author keywords

biocatalysis; cytochrome P450; directed evolution; non natural enzymes

Indexed keywords

CARBENE; CYTOCHROME P450; ENZYME; IMINE; METHANE; PHENYLNITRENE;

ANALOGS AND DERIVATIVES; BACTERIUM; BIOCATALYSIS; CATALYSIS; CHEMISTRY; DIRECTED MOLECULAR EVOLUTION; GENETICS; HYDROGEN BOND; METABOLISM; MOLECULAR EVOLUTION; PROCEDURES; PROTEIN ENGINEERING;

BACTERIA; BIOCATALYSIS; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; DIRECTED MOLECULAR EVOLUTION; ENZYMES; EVOLUTION, MOLECULAR; HYDROGEN BONDING; IMINES; METHANE; PROTEIN ENGINEERING;

EID: 84949190783     PISSN: 00335835     EISSN: 14698994     Source Type: Journal    
DOI: 10.1017/S003358351500013X     Document Type: Review

References (34)

1. AHARONI, A., GAIDUKOV, L., KHERSHONSKY, O., GOULD, S. M., ROODVELDT, C. & TAWFIK, D. S. (2005). The 'evolvability' of promiscuous protein functions. Nature Genetics 37, 73-76.
2. BABTIE, A., TOKURIKI, N. & HOLLFELDER, F. (2010). What makes an en-zyme promiscuous? Current Opinion in Chemical Biology 14, 200-207.
3. BAIER, F. & TOKURIKI, N. (2014). Connectivity between catalytic landscapes of the Metallo-ß-lactamase superfamily. Journal of Molecular Biology 426, 2442-2456.
4. BARTLETT, G. J., BORKAKOTI, N. & THRONTON, J. M. (2003). Catalysing new reactions during evolution: economy of residues and mechanism. Journal of Molecular Biology 331, 829-860.
5. BAUMANN, L. K., MBUVI, H. M., GUODONG, D. & WOO, L. K. (2007). Iron prophyrin catalyzed N-H insertion reactions with ethyl dia-zoacetate. Organometallics 26, 3995-4002.
6. BORDEAUX, M., TYAGI, V. & FASAN, R. (2015). Highly diastereoselec-tive and enantioselective olefin cyclopropanation using engineered myoglobin-based catalysts. Angewandte Chemie 127, 1764-1768.
7. BRESLOW, R. & GELLMAN, S. H. (1983). Intramolecular nitrene carbon-hydrogen insertions mediated by transition-metal complexes as nitrogen analogs of cytochrome P-450 reactions. Journal of the American Chemical Society 105, 6728-6729.
8. CHEN, Y., FIELDS, K. B. & ZHANG, X. P. (2004). Bromoporphyrins as versatile synthons for modular construction of chiral porphyrins: cobalt-catalyzed highly enantioselective and diastereoselective cyclopropanation. Journal of the American Chemical Society 126, 14718-14719.
9. COELHO, P. S., BRUSTAD, E. M., KANNAN, A. & ARNOLD, F. H. (2013a). Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes. Science 339, 307-310.
10. COELHO, P.S., WANG, Z.J., ENER, M.E., BARIL, S.A., KANNAN, A., ARNOLD, F. H. & BRUSTAD, E. M. (2013b). A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo. Nature Chemical Biology 9, 485-487.
11. COPLEY, S. D. (2003). Enzymes with extra talents: moonlighting functions and catalytic promiscuity. Current Opinion in Chemical Biology 7, 265-272.
12. FARWELL, C. C., MCINTOSH, J. A., HYSTER, T. K., WANG, Z. J. & ARNOLD, F. H. (2014). Enantioselective imidation of sulfides via enzyme-catalyzed intermolecular nitrogen-atom transfer. Journal of the American Chemical Society 136, 8766-8771.
13. FARWELL, C.C., ZHANG, R.K., MCINTOSH, J.A., HYSTER, T.K. & ARNOLD, F. H. (2015). Enantioselective enzyme-catalyzed aziridi-nation enabled by active-site evolution of a cytochrome P450. ACS Central Science 1, 89-93.
14. GATTI-LAFRANCONI, P. & HOLLFELDER, F. (2013). Flexibility and reactivity in promiscuous enzymes. ChemBioChem 14, 285-292.
15. GERLT, J. A. & BABBITT, P. C. (2009). Mechanistically diverse enzyme superfamilies: the importance of chemistry in the evolution of catalysis. Current Opinion in Chemical Biology 13, 10-18.
16. GERLT, J. A. & BABBITT, P. C. (2011). Divergent evolution of enzymatic function: mechanistically diverse superfamilies and functionally distinct superfamilies. Annual Review of Biochemistry 70, 209-246.
17. HAMMER, S.C., MARJANOVIC, A., DOMINICUS, J.M., NESTL, B.M. & HAUER, B. (2015). Squalene hopene cyclases are protanases for stereoselective Bronsted acid catalysis. Nature Chemical Biology 11, 121-126.
18. HEEL, T., MCINTOSH, J. A., DODANI, S. C., MEYEROWITZ, J. T. & ARNOLD, F. H. (2014). Non-natural olefin cyclopropanation catalyzed by diverse cytochrome P450s and other hemoproteins. ChemBioChem 15, 2556-2562.
19. HYSTER, T.K., FARWELL, C.C., BULLER, A.R., MCINTOSH, J.A. & ARNOLD, F. H. (2014). Enzyme-controlled nitrogen-atom transfer enables regiodivergent C-H amination. Journal of the American Chemical Society 136, 15505-15508.
20. KAZLAUSKAS, R. J. (2005). Enhancing catalytic promiscuity for bioca-talysis. Current Opinion in Chemical Biology 9, 195-201.
21. LU, H. & ZHANG, X. P. (2011). Catalytic C-H functionalization by metalloporphyrins: recent developments and future directions. Chemical Society Reviews 40, 1899-1909.
22. MCINTOSH, J. A., COELHO, P. S., FARWELL, C. C., WANG, Z. J., LEWIS, J. C., BROWN, T. R. & ARNOLD, F. H. (2013). Enantioselective intramolecular C-H amination catalyzed by engineered cytochrome P450 enzymes in vitro and in vivo. Angewandte Chemie International Edition in English 52, 9309-9312.
23. MCINTOSH, J. A., FARWELL, C. C. & ARNOLD, F. H. (2014). Expanding P450 catalytic reaction space through evolution and engineering. Current Opinion in Chemical Biology 19, 126-134.
24. MEIER, M.M., RAJENDRAN, C., MALISI, C., FOX, N.G., XU, C., SCHLEE, S., BARONDEAU, D.P., HÖCKER, B., STERNER, R. & RAUSHEL, F. M. (2013). Journal of the American Chemical Society 135, 11670-11677.
25. O'BRIEN, P. J. & HERSCHLAG, D. (1999). Catalytic promiscuity and the evolution of new enzymatic activities. Chemistry and Biology 6, R91-R105.
26. RENATA, H., WANG, Z. J. & ARNOLD, F. H. (2015). Non-natural enzymes: expanding the enzyme universe by evolution and mechanism-guided design. Angewandte Chemie International Edition in English 54, 3351-3367.
27. SEEBECK, F. & HILVERT, D. (2003). Conversion of a PLP-dependent racemase into an aldolase by a single active site mutation. Journal of the American Chemical Society 125, 10158-10159.
28. 3 C-H amination with arylsulfonyl azide substrates. ACS Catalysis 4, 546-552.
29. SVASTITS, E. W., DAWSON, J. H., BRESLOW, R. & GELLMAN, S. H. (1985). Functionalized nitrogen atom transfer catalyzed by cytochrome P-450. Journal of the American Chemical Society 107, 6427-6428.
30. TOKURIKI, N. & TAWFIK, D. S. (2009). Protein dynamism and evolva-bility. Science 324, 203-207.
31. TOSCANO, M. D., WOYCECHOWSKY, K. J. & HILVERT, D.(2007). Minimalist active-site redesign: teaching old enzymes new tricks. Angewandte Chemie International Edition in English 46, 3212-3236.
32. WANG, Z.J., PECK, N.E., RENATA, H. & ARNOLD, F.H. (2014a). Cytochrome P450-catalyzed insertion of carbenoids into N-H bonds. Chemical Sciences 5, 598-601.
33. WANG, Z. J., RENATA, H., PECK, N. E., FARWELL, C. C., COELHO, P. S. & ARNOLD, F. H. (2014b). Improved cyclopropanation activity of histidine-ligated cytochrome P450 enables formal synthesis of levomilnacipran. Angewandte Chemie 126, 6928-6931.
34. WOLF, J. R., HAMAKER, C. G., DJUKIC, J.-P., KODADEK, T. & WOO, L. K. (1995). Shape and stereoselective cyclopropanation of alkenes catalyzed by iron porphyrins. Journal of the American Chemical Society 117, 9194-9199.