A Well-Defined Osmium-Cupin Complex: Hyperstable Artificial Osmium Peroxygenase

Journal of the American Chemical Society

Volumn 139, Issue 14, 2017, Pages 5149-5155

  Fujieda, Nobutaka ^a   Nakano, Takumi ^a   Taniguchi, Yuki ^a   Ichihashi, Haruna ^a   Sugimoto, Hideki ^a   Morimoto, Yuma ^a   Nishikawa, Yosuke ^a   Kurisu, Genji ^a   Itoh, Shinobu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CRYSTAL ATOMIC STRUCTURE; HYDROCARBONS; HYDROXYLATION; ISOMERS; MOLECULES; PLANTS (BOTANY); PROTEINS; SCAFFOLDS (BIOLOGY); SPECTROSCOPIC ANALYSIS; THERMODYNAMIC STABILITY;

ATOMIC RESOLUTION; DISPROPORTIONATIONS; METAL SUBSTITUTION; OCTAHEDRAL COORDINATION GEOMETRY; SITE DIRECTED MUTAGENESIS; STERIC HINDRANCES; THERMOTOGA MARITIMA; X RAY CRYSTAL STRUCTURES;

CATALYST ACTIVITY;

ALKENE DERIVATIVE; BACTERIAL PROTEIN; CUPIN; IMIDAZOLE DERIVATIVE; OSMIUM DERIVATIVE; OSMIUM PEROXYGENASE; TM1459 PROTEIN; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; ATOMIC EMISSION SPECTROMETRY; BIOCATALYST; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLOADDITION; DIHYDROXYLATION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDROGEN BOND; ISOMER; METAL BINDING; NONHUMAN; PROTEIN DENATURATION; PROTEIN FAMILY; PROTEIN FOLDING; PROTEIN MOTIF; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; PROTEIN SUBUNIT; PROTON NUCLEAR MAGNETIC RESONANCE; REGIOSELECTIVITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTRATE CONCENTRATION; THERMOSTABILITY; THERMOTOGA MARITIMA; TURNOVER NUMBER;

EID: 85018291716     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.7b00675     Document Type: Article

References (48)

1. Bornscheuer, U. T.; Huisman, G. W.; Kazlauskas, R. J.; Lutz, S.; Moore, J. C.; Robins, K. Nature 2012, 485, 185 10.1038/nature11117
2. Ward, T. R. Chem.-Eur. J. 2005, 11, 3798 10.1002/chem.200401232
3. Boersma, A. J.; Megens, R. P.; Feringa, B. L.; Roelfes, G. Chem. Soc. Rev. 2010, 39, 2083 10.1039/b811349c
4. Park, S.; Sugiyama, H. Angew. Chem., Int. Ed. 2010, 49, 3870 10.1002/anie.200905382
5. Köhler, V.; Wilson, Y. M.; Lo, C.; Sardo, A.; Ward, T. R. Curr. Opin. Biotechnol. 2010, 21, 744 10.1016/j.copbio.2010.09.004
6. Heinisch, T.; Ward, T. R. Curr. Opin. Chem. Biol. 2010, 14, 184 10.1016/j.cbpa.2009.11.026
7. Yu, F.; Cangelosi, V. M.; Zastrow, M. L.; Tegoni, M.; Plegaria, J. S.; Tebo, A. G.; Mocny, C. S.; Ruckthong, L.; Qayyum, H.; Pecoraro, V. L. Chem. Rev. 2014, 114, 3495 10.1021/cr400458x
8. Bos, J.; Roelfes, G. Curr. Opin. Chem. Biol. 2014, 19, 135 10.1016/j.cbpa.2014.02.002
9. Matsuo, T.; Hirota, S. Bioorg. Med. Chem. 2014, 22, 5638 10.1016/j.bmc.2014.06.021
10. Hoarau, M.; Hureau, C.; Gras, E.; Faller, P. Coord. Chem. Rev. 2016, 308, 445 10.1016/j.ccr.2015.05.011
11. Pàmies, O.; Diéguez, M.; Bäckvall, J.-E. Adv. Synth. Catal. 2015, 357, 1567 10.1002/adsc.201500290
12. Jeschek, M.; Reuter, R.; Heinisch, T.; Trindler, C.; Klehr, J.; Panke, S.; Ward, T. R. Nature 2016, 537, 661 10.1038/nature19114
13. Key, H. M.; Dydio, P.; Clark, D. S.; Hartwig, J. F. Nature 2016, 534, 534 10.1038/nature17968
14. Dydio, P.; Key, H. M.; Nazarenko, A.; Rha, J. Y.-E.; Seyedkazemi, V.; Clark, D. S.; Hartwig, J. F. Science 2016, 354, 102 10.1126/science.aah4427
15. Ueno, T.; Tabe, H.; Tanaka, Y. Chem.-Asian J. 2013, 8, 1646 10.1002/asia.201300347
16. Lewis, J. C. Curr. Opin. Chem. Biol. 2015, 25, 27 10.1016/j.cbpa.2014.12.016
17. Song, W. J.; Tezcan, F. A. Science 2014, 346, 1525 10.1126/science.1259680
18. Fujieda, N.; Schätti, J.; Stuttfeld, E.; Ohkubo, K.; Maier, T.; Fukuzumi, S.; Ward, T. R. Chem. Sci. 2015, 6, 4060 10.1039/C5SC01065A
19. Bornscheuer, U. T.; Kazlauskas, R. J. Angew. Chem., Int. Ed. 2004, 43, 6032 10.1002/anie.200460416
20. Pordea, A. Curr. Opin. Chem. Biol. 2015, 25, 124 10.1016/j.cbpa.2014.12.035
21. Engeseth, H. R.; McMillin, D. R. Biochemistry 1986, 25, 2448 10.1021/bi00357a023
22. Okrasa, K.; Kazlauskas, R. J. Chem.-Eur. J. 2006, 12, 1587 10.1002/chem.200501413
23. Fernández-Gacio, A.; Codina, A.; Fastrez, J.; Riant, O.; Soumillion, P. ChemBioChem 2006, 7, 1013 10.1002/cbic.200600127
24. Jing, Q.; Okrasa, K.; Kazlauskas, R. J. Chem.-Eur. J. 2009, 15, 1370 10.1002/chem.200801673
25. Jing, Q.; Kazlauskas, R. J. ChemCatChem 2010, 2, 953 10.1002/cctc.201000159
26. Key, H. M.; Clark, D. S.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8261 10.1021/jacs.5b04431
27. Jaroszewski, L.; Schwarzenbacher, R.; von Delft, F.; McMullan, D.; Brinen, L. S.; Canaves, J. M.; Dai, X.; Deacon, A. M.; DiDonato, M.; Elsliger, M.-A.; Eshagi, S.; Floyd, R.; Godzik, A.; Grittini, C.; Grzechnik, S. K.; Hampton, E.; Levin, I.; Karlak, C.; Klock, H. E.; Koesema, E.; Kovarik, J. S.; Kreusch, A.; Kuhn, P.; Lesley, S. A.; McPhillips, T. M.; Miller, M. D.; Morse, A.; Moy, K.; Ouyang, J.; Page, R.; Quijano, K.; Reyes, R.; Rezezadeh, F.; Robb, A.; Sims, E.; Spraggon, G.; Stevens, R. C.; van den Bedem, H.; Velasquez, J.; Vincent, J.; Wang, X.; West, B.; Wolf, G.; Xu, Q.; Hodgson, K. O.; Wooley, J.; Wilson, I. A. Proteins: Struct., Funct., Genet. 2004, 56, 611 10.1002/prot.20130
28. Hajnal, I.; Faber, K.; Schwab, H.; Hall, M.; Steiner, K. Adv. Synth. Catal. 2015, 357, 3309 10.1002/adsc.201500608
29. Que, L.; Tolman, W. B. Nature 2008, 455, 333 10.1038/nature07371
30. Sugimoto, H.; Kitayama, K.; Mori, S.; Itoh, S. J. Am. Chem. Soc. 2012, 134, 19270 10.1021/ja309566c
31. Kokubo, T.; Sugimoto, T.; Uchida, T.; Tanimoto, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1983, 0, 769 10.1039/C39830000769
32. Köhler, V.; Mao, J.; Heinisch, T.; Pordea, A.; Sardo, A.; Wilson, Y. M.; Knörr, L.; Creus, M.; Prost, J.; Schirmer, T.; Ward, T. R. Angew. Chem., Int. Ed. 2011, 50, 10863 10.1002/anie.201103632
33. Konieczny, S.; Leurs, M.; Tiller, J. C. ChemBioChem 2015, 16, 83 10.1002/cbic.201402339
34. Meeuwissen, J.; Reek, J. N. H. Nat. Chem. 2010, 2, 615 10.1038/nchem.744
35. Prier, C. K.; Arnold, F. H. J. Am. Chem. Soc. 2015, 137, 13992 10.1021/jacs.5b09348
36. Mayboroda, A.; Rheinwald, G.; Lang, H. Inorg. Chim. Acta 2003, 355, 69 10.1016/S0020-1693(03)00297-4
37. Dobson, J. C.; Takeuchi, K. J.; Pipes, D. W.; Geselowitz, D. A.; Meyer, T. J. Inorg. Chem. 1986, 25, 2357 10.1021/ic00234a017
38. Mizutani, K.; Mikami, B.; Aibara, S.; Hirose, M. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2005, 61, 1636 10.1107/S090744490503266X
39. Lisi, G. P.; Hughes, R. P.; Wilcox, D. E. JBIC, J. Biol. Inorg. Chem. 2016, 21, 659 10.1007/s00775-016-1375-6
40. Ma, J. K.; Bishop, G. R.; Davidson, V. L. Arch. Biochem. Biophys. 2005, 444, 27 10.1016/j.abb.2005.09.016
41. Sugimoto, H.; Matsunami, C.; Koshi, C.; Yamasaki, M.; Umakoshi, K.; Sasaki, Y. Bull. Chem. Soc. Jpn. 2001, 74, 2091 10.1246/bcsj.74.2091
42. Sugimoto, H.; Ashikari, K.; Itoh, S. Chem.-Asian J. 2013, 8, 2154 10.1002/asia.201300329
43. Bergstad, K.; Jonsson, S. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 10424 10.1021/ja991710b
44. Chen, M. S.; White, M. C. Science 2007, 318, 783 10.1126/science.1148597
45. List, B.; Barbas, C. F.; Lerner, R. a. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 15351 10.1073/pnas.95.26.15351
46. Wahler, D.; Badalassi, F.; Crotti, P.; Reymond, J. Chem.-Eur. J. 2002, 8, 3211 10.1002/1521-3765(20020715)8:14<3211::AID-CHEM3211>3.0.CO;2-G
47. Dunwell, J. M.; Purvis, A.; Khuri, S. Phytochemistry 2004, 65, 7 10.1016/j.phytochem.2003.08.016
48. Chavez, F.; Banerjee, A.; Sljivic, B. Modeling the metal binding site in cupin proteins, On Biomimetics; Pramatarova, L., Ed.; InTech: Rijeka, 2011.