Stereoselectivity and Structural Characterization of an Imine Reductase (IRED) from Amycolatopsis orientalis

ACS Catalysis

Volumn 6, Issue 6, 2016, Pages 3880-3889

  Aleku, Godwin A ^a   Man, Henry ^b   France, Scott P ^a   Leipold, Friedemann ^a   Hussain, Shahed ^a   Toca Gonzalez, Laura ^a   Marchington, Rebecca ^a   Hart, Sam ^b   Turkenburg, Johan P ^b   Grogan, Gideon ^b   Turner, Nicholas J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

biocatalysis; chiral amine; imine reductase; NADPH; oxidoreductase

Indexed keywords

CARBON; CATALYSIS; COBALT COMPOUNDS; ENZYMES; STEREOSELECTIVITY; SUBSTRATES;

BIOCATALYSIS; CHIRAL AMINES; IMINE REDUCTASE; NADPH; OXIDOREDUCTASES;

NITROGEN COMPOUNDS;

EID: 84973922985     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b00782     Document Type: Article

References (40)

1. Höhne, M.; Bornscheuer, U. T. ChemCatChem 2009, 1, 42-51 10.1002/cctc.200900110
2. Buchholz, S.; Gröger, H. Biocatalysis in the Pharmaceutical and Biotechnology Industries; Patel, R., Ed; CRC Press: Boca Raton, Florida, 2006; pp 829-847.
3. Mathew, S.; Yun, H. ACS Catal. 2012, 2, 993-1001 10.1021/cs300116n
4. Ghislieri, D.; Green, A. P.; Pontini, M.; Willies, S. C.; Rowles, I.; Frank, A.; Grogan, G.; Turner, N. J. J. Am. Chem. Soc. 2013, 135, 10863-10869 10.1021/ja4051235
5. Abrahamson, M. J.; Vázquez-Figueroa, E.; Woodall, N. B.; Moore, J. C.; Bommarius, A. S. Angew. Chem., Int. Ed. 2012, 51, 3969-3972 10.1002/anie.201107813
6. Mutti, F. G.; Knaus, T.; Scrutton, N. S.; Breuer, M.; Turner, N. J. Science 2015, 349, 1525-2529 10.1126/science.aac9283
7. Chen, F.-F.; Liu, Y.-Y.; Zheng, G.-W.; Xu, J.-H. ChemCatChem 2015, 7, 3838-3841 10.1002/cctc.201500785
8. Mitsukura, K.; Suzuki, M.; Tada, K.; Yoshida, T.; Nagasawa, T. Org. Biomol. Chem. 2010, 8, 4533-4535 10.1039/C0OB00353K
9. Mitsukura, K.; Suzuki, M.; Shinoda, S.; Kuramoto, T.; Yoshida, T.; Nagasawa, T. Biosci., Biotechnol., Biochem. 2011, 75, 1778-1782 10.1271/bbb.110303
10. Mitsukura, K.; Kuramoto, T.; Yoshida, T.; Kimoto; Yamamoto, H.; Nagasawa, T. Appl. Microbiol. Biotechnol. 2013, 97, 8079-8086 10.1007/s00253-012-4629-4
11. Leipold, F.; Hussain, S.; Ghislieri, D.; Turner, N. J. ChemCatChem 2013, 5, 3505-3508 10.1002/cctc.201300539
12. Huber, T.; Schneider, L.; Präg, A.; Gerhardt, S.; Einsle, O.; Müller, M. ChemCatChem 2014, 6, 2248-2252 10.1002/cctc.201402218
13. Scheller, P. N.; Fademrecht, S.; Hofelzer, S.; Pleiss, J.; Leipold, F.; Turner, N. J.; Nestl, B. M.; Hauer, B. ChemBioChem 2014, 15, 2201-2204 10.1002/cbic.201402213
14. Gand, M.; Müller, H.; Wardenga, R.; Höhne, M. J. Mol. Catal. B: Enzym. 2014, 110, 126-132 10.1016/j.molcatb.2014.09.017
15. Hussain, S.; Leipold, F.; Man, H.; Wells, E.; France, S.; Mulholland, K. R.; Grogan, G.; Turner, N. J. ChemCatChem 2015, 7, 579-583 10.1002/cctc.201402797
16. Rodríguez-Mata, M.; Frank, A.; Wells, E.; Leipold, F.; Turner, N. J.; Hart, S.; Turkenburg, J. P.; Grogan, G. ChemBioChem 2013, 14, 1372-1379 10.1002/cbic.201300321
17. Wetzl, D.; Berrera, M.; Sandon, N.; Fishlock, D.; Ebeling, M.; MuÌller, M.; Hanlon, S.; Wirz, B.; Iding, H. ChemBioChem 2015, 16, 1749-1756 10.1002/cbic.201500218
18. Schrittwieser, J.; Velikogne, S.; Kroutil, W. Adv. Synth. Catal. 2015, 357, 1655-1685 10.1002/adsc.201500213
19. Grogan, G.; Turner, N. J. Chem.-Eur. J. 2016, 22, 1900-1907 10.1002/chem.201503954
20. Leipold, F.; Hussain, S.; France, S. P.; Turner, N. J. In Biocatalysis in Organic Synthesis, Faber, K.; Fessner, W.; Turner, N., Eds., Science of Synthesis Reference Library; Thieme Verlag: Stuttgart, 2015; Vol. 2, pp 359-381.
21. Fleury-Brégeot, N.; de la Fuente, V.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346-1371 10.1002/cctc.201000078
22. Lokanath, N. K.; Ohshima, N.; Takio, K.; Shiromizu, I.; Kuroishi, C.; Okazaki, N.; Kuramitsu, S.; Yokoyama, S.; Miyano, M.; Kunishima, N. J. Mol. Biol. 2005, 352, 905-917 10.1016/j.jmb.2005.07.068
23. Gourley, D. G.; Schuttelkopf, A. W.; Leonard, G. A.; Luba, J.; Hardy, L. W.; Beverley, S. M.; Hunter, W. N. Nat. Struct. Biol. 2001, 8, 521-525 10.1038/88584
24. Man, H.; Wells, E.; Hussain, S.; Leipold, F.; Hart, S.; Turkenburg, J. P.; Turner, N. J.; Grogan, G. ChemBioChem 2015, 16, 1052-1059 10.1002/cbic.201402625
25. Pham, T.; Phillips, R. S.; Ljungdahl, L. G. J. Am. Chem. Soc. 1989, 111, 1935-1936 10.1021/ja00187a089
26. Li, H.; Luan, Z.-J.; Zheng, G.-W.; Xu, J.-H. Adv. Synth. Catal. 2015, 357, 1692-1696 10.1002/adsc.201500160
27. Li, H.; Zhang, G.-X.; Li, L.-M.; Ou, Y.-S.; Wang, M.-Y.; Li, C.-X.; Zheng, G.-W.; Xu, J.-H. ChemCatChem 2016, 8, 724-727 10.1002/cctc.201501170
28. Holm, L.; Rosenström, P. Nucleic Acids Res. 2010, 38, W545-W549 10.1093/nar/gkq366
29. Grosch, J.-H.; Loderer, C.; Jestel, T.; Ansorge-Schumacher, M.; Spieß, A. C. J. Mol. Catal. B: Enzym. 2015, 112, 45-53 10.1016/j.molcatb.2014.12.001
30. Olsen, S. N. Thermochim. Acta 2006, 448, 12-18 10.1016/j.tca.2006.06.019
31. Patel, J. M.; Phillips, R. S. ACS Catal. 2014, 4, 692-694 10.1021/cs4010997
32. Flot, D.; Mairs, T.; Giraud, T.; Guijarro, M.; Lesourd, M.; Rey, V.; van Brussel, D.; Morawe, C.; Borel, C.; Hignette, O. et al. J. Synchrotron Radiat. 2010, 17, 107-118 10.1107/S0909049509041168
33. Kabsch, W. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 125-132 10.1107/S0907444909047337
34. Evans, P. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 72-82 10.1107/S0907444905036693
35. Winter, G. J. Appl. Crystallogr. 2010, 43, 186-190 10.1107/S0021889809045701
36. Vagin, A.; Teplyakov, A. J. Appl. Crystallogr. 1997, 30, 1022-1025 10.1107/S0021889897006766
37. Emsley, P.; Cowtan, K. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132 10.1107/S0907444904019158
38. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240-255 10.1107/S0907444996012255
39. Schüttelkopf, A. W.; van Aalten, D. M. F. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 1355-1363 10.1107/S0907444904011679
40. Laskowski, R. A.; Macarthur, M. W.; Moss, D. S.; Thornton, J. M. J. Appl. Crystallogr. 1993, 26, 283-291 10.1107/S0021889892009944