A Highly Active Biohybrid Catalyst for Olefin Metathesis in Water: Impact of a Hydrophobic Cavity in a β-Barrel Protein

ACS Catalysis

Volumn 5, Issue 12, 2015, Pages 7519-7522

  Sauer, Daniel F ^a   Himiyama, Tomoki ^b   Tachikawa, Kengo ^b   Fukumoto, Kazuki ^b   Onoda, Akira ^b   Mizohata, Eiichi ^b   Inoue, Tsuyoshi ^b   Bocola, Marco ^a   Schwaneberg, Ulrich ^a   Hayashi, Takashi ^b   Okuda, Jun ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

biohybrid catalysis; chemogenetic approach; metalloenzymes; metathesis; ruthenium

Indexed keywords

CATALYSTS; OLEFINS; PROTEINS; RUTHENIUM;

CATALYST PRECURSORS; CHEMOGENETIC APPROACH; HYDROPHOBIC CAVITIES; METALLOENZYMES; METATHESIS; OLEFIN METATHESIS REACTIONS; ORGANIC COSOLVENTS; RING CLOSING METATHESIS;

HYDROPHOBICITY;

EID: 84948775386     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b01792     Document Type: Article

References (36)

1. Matsuo, T.; Hirota, S. Bioorg. Med. Chem. 2014, 22, 5638-5656 10.1016/j.bmc.2014.06.021
2. Hayashi, T.; Sano, Y.; Onoda, A. Isr. J. Chem. 2015, 55, 76-84 10.1002/ijch.201400123
3. Steinreiber, J.; Ward, T. R. Coord. Chem. Rev. 2008, 252, 751-766 10.1016/j.ccr.2007.09.016
4. Lu, Y.; Yeung, N.; Sieracki, N.; Marshall, N. M. Nature 2009, 460, 855-862 10.1038/nature08304
5. Lu, Y. Angew. Chem., Int. Ed. 2006, 45, 5588-5601 10.1002/anie.200600168
6. Lu, Y. Angew. Chem. 2006, 118, 5714-5728 10.1002/ange.200600168
7. Ueno, T.; Tabe, H.; Tanaka, Y. Chem.-Asian J. 2013, 8, 1646-1660 10.1002/asia.201300347
8. Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1978, 100, 306-307 10.1021/ja00469a064
9. Collot, J.; Gradinaru, J.; Humbert, N.; Skander, M.; Zocchi, A.; Ward, T. R. J. Am. Chem. Soc. 2003, 125, 9030-9031 10.1021/ja035545i
10. Zimbron, J. M.; Heinisch, T.; Schmid, M.; Hamels, D.; Nogueira, E. S.; Schirmer, T.; Ward, T. R. J. Am. Chem. Soc. 2013, 135, 5384-5388 10.1021/ja309974s
11. Muñoz Robles, V.; Dürrenberger, M.; Heinisch, T.; Lledós, A.; Schirmer, T.; Ward, T. R.; Maréchal, J.-D. J. Am. Chem. Soc. 2014, 136, 15676-15683 10.1021/ja508258t
12. Lo, C.; Ringenberg, M. R.; Gnandt, D.; Wilson, Y.; Ward, T. R. Chem. Commun. 2011, 47, 12065-12067 10.1039/c1cc15004a
13. Yamamura, K.; Kaiser, E. T. J. Chem. Soc., Chem. Commun. 1976, 0, 830-831 10.1039/c39760000830
14. Levine, H. L.; Nakagawa, Y.; Kaiser, E. T. Biochem. Biophys. Res. Commun. 1977, 76, 64-70 10.1016/0006-291X(77)91668-0
15. Zhao, J.; Kajetanowicz, A.; Ward, T. R. Org. Biomol. Chem. 2015, 13, 5652-5655 10.1039/C5OB00428D
16. Mayer, C.; Gillingham, D. G.; Ward, T. R.; Hilvert, D. Chem. Commun. 2011, 47, 12068-12070 10.1039/c1cc15005g
17. Matsuo, T.; Imai, C.; Yoshida, T.; Saito, T.; Hayashi, T.; Hirota, S. Chem. Commun. 2012, 48, 1662-1664 10.1039/c2cc16898g
18. Onoda, A.; Fukumoto, K.; Arlt, M.; Bocola, M.; Schwaneberg, U.; Hayashi, T. Chem. Commun. 2012, 48, 9756-9758 10.1039/c2cc35165j
19. Fukumoto, K.; Onoda, A.; Mizohata, E.; Bocola, M.; Inoue, T.; Schwaneberg, U.; Hayashi, T. ChemCatChem 2014, 6, 1229-1235 10.1002/cctc.201301055
20. Zhang, C.; Srivastava, P.; Ellis-Guardiola, K.; Lewis, J. C. Tetrahedron 2014, 70, 4245-4249 10.1016/j.tet.2014.03.008
21. Onoda, A.; Kihara, Y.; Fukumoto, K.; Sano, Y.; Hayashi, T. ACS Catal. 2014, 4, 2645-2648 10.1021/cs500392e
22. Khan, R. K. M.; Torker, S.; Hoveyda, A. H. J. Am. Chem. Soc. 2013, 135, 10258-10261 10.1021/ja404208a
23. Koh, M. J.; Khan, R. K. M.; Torker, S.; Yu, M.; Mikus, M. S.; Hoveyda, A. H. Nature 2015, 517, 181-186 10.1038/nature14061
24. Keitz, B. K.; Endo, K.; Patel, P. R.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 693-699 10.1021/ja210225e
25. Skowerski, K.; Szczepaniak, G.; Wierzbicka, C.; Gulajski, L.; Bieniek, M.; Grela, K. Catal. Sci. Technol. 2012, 2, 2424-2427 10.1039/c2cy20320k
26. Hong, S. H.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 3508-3509 10.1021/ja058451c
27. Jordan, J. P.; Grubbs, R. H. Angew. Chem. 2007, 119, 5244-5247 10.1002/ange.200701258
28. Jordan, J. P.; Grubbs, R. H. Angew. Chem., Int. Ed. 2007, 46, 5152-5155 10.1002/anie.200701258
29. Philippart, F.; Arlt, M.; Gotzen, S.; Tenne, S.-J.; Bocola, M.; Chen, H.-H.; Zhu, L.; Schwaneberg, U.; Okuda, J. Chem.-Eur. J. 2013, 19, 13865-13871 10.1002/chem.201301515
30. Sauer, D. F.; Bocola, M.; Broglia, C.; Arlt, M.; Zhu, L.; Brocker, M.; Schwaneberg, U.; Okuda, J. Chem.-Asian J. 2015, 10, 177-182 10.1002/asia.201403005
31. Krieger, E.; Darden, T.; Nabuurs, S. B.; Finkelstein, A.; Vriend, G. Proteins: Struct., Funct., Genet. 2004, 57, 678-683 10.1002/prot.20251
32. Bianchetti, C. M.; Blouin, G. C.; Bitto, E.; Olson, J. S.; Phillips, G. N. Proteins: Struct., Funct., Genet. 2010, 78, 917-931 10.1002/prot.22617
33. Gawin, R.; Czarnecka, P.; Grela, K. Tetrahedron 2010, 66, 1051-1056 10.1016/j.tet.2009.11.009
34. Lynn, D. M.; Mohr, B.; Grubbs, R. H.; Henling, L. M.; Day, M. W. J. Am. Chem. Soc. 2000, 122, 6601-6609 10.1021/ja0003167
35. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29 10.1021/ar000114f
36. P'Poo, S. J.; Schanz, H.-J. J. Am. Chem. Soc. 2007, 129, 14200-14212 10.1021/ja071938w