A Biocatalytic Aza-Achmatowicz Reaction

ACS Catalysis

Volumn 6, Issue 9, 2016, Pages 5904-5907

  Fernández Fueyo, Elena ^a   Younes, Sabry H H ^a,b   Van Rootselaar, Stefan ^c   Aben, René W M ^c   Renirie, Rokus ^d   Wever, Ron ^e   Holtmann, Dirk ^f   Rutjes, Floris P J T ^c   Hollmann, Frank ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b Sohag University   (Egypt)

^c RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^d UNIVERSITY OF AMSTERDAM   (Netherlands)

^e UNIVERSITY OF AMSTERDAM   (Netherlands)

^f DECHEMA FORSCHUNGSINSTITUT   (Germany)

Author keywords

Achmatowicz reaction; biocatalysis; hypohalogenites; oxidation; peroxidase

Indexed keywords

ACHMATOWICZ REACTION; BIOCATALYSIS; CATALYTIC AMOUNTS; HYPOHALOGENITES; PEROXIDASE;

OXIDATION;

EID: 84984920969     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b01636     Document Type: Article

References (22)

1. Achmatowicz, O., Jr.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973-1996 10.1016/S0040-4020(01)98229-8
2. Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 1998, 105-114 10.1055/s-1998-1584
3. Merino, P.; Tejero, T.; Delso, J. I.; Matute, R. Curr. Org. Chem. 2007, 11, 1076-1091 10.2174/138527207781369245
4. van der Pijl, F.; van Delft, F. L.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2015, 2015, 4811-4829 10.1002/ejoc.201500321
5. Ransborg, L. K.; Lykke, L.; Hammer, N.; Naesborg, L.; Jorgensen, K. A. Chem. Commun. 2014, 50, 7604-7606 10.1039/c4cc03815k
6. Cheng, K. V.; Kelly, A. R.; Kohn, R. A.; Dweck, J. F.; Walsh, P. J. Org. Lett. 2009, 11, 2703-2706 10.1021/ol900905r
7. van der Pijl, F.; van Delft, F. L.; Rutjes, F. P. J. T. Bioorg. Med. Chem. 2015, 23, 2721-2729 10.1016/j.bmc.2014.12.045
8. van der Pijl, F.; Harmel, R. K.; Richelle, G. J. J.; Janssen, P.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2014, 16, 2038-2041 10.1021/ol500633u
9. Thiel, D.; Doknić, D.; Deska, J. Nat. Commun. 2014, 5, 5278 10.1038/ncomms6278
10. Ni, Y.; Fernández-Fueyo, E.; Baraibar, A. G.; Ullrich, R.; Hofrichter, M.; Yanase, H.; Alcalde, M.; van Berkel, W. J. H.; Hollmann, F. Angew. Chem., Int. Ed. 2016, 55, 798-801 10.1002/anie.201507881
11. Getrey, L.; Krieg, T.; Hollmann, F.; Schrader, J.; Holtmann, D. Green Chem. 2014, 16, 1104-1108 10.1039/C3GC42269K
12. Churakova, E.; Kluge, M.; Ullrich, R.; Arends, I. W. C. E.; Hofrichter, M.; Hollmann, F. Angew. Chem., Int. Ed. 2011, 50, 10716-10719 10.1002/anie.201105308
13. Perez, D. I.; Mifsud Grau, M.; Arends, I. W. C. E.; Hollmann, F. Chem. Commun. 2009, 44, 6848-6850 10.1039/b915078a
14. Bormann, S.; Gomez Baraibar, A.; Ni, Y.; Holtmann, D.; Hollmann, F. Catal. Sci. Technol. 2015, 5, 2038-2052 10.1039/C4CY01477D
15. Hasan, Z.; Renirie, R.; Kerkman, R.; Ruijssenaars, H. J.; Hartog, A. F.; Wever, R. J. Biol. Chem. 2006, 281, 9738-9744 10.1074/jbc.M512166200
16. Renirie, R.; Pierlot, C.; Aubry, J.-M.; Hartog, A. F.; Schoemaker, H. E.; Alsters, P. L.; Wever, R. Adv. Synth. Catal. 2003, 345, 849-858 10.1002/adsc.200303008
17. ten Brink, H. B.; Dekker, H. L.; Schoemaker, H. E.; Wever, R. J. Inorg. Biochem. 2000, 80, 91-98 10.1016/S0162-0134(00)00044-1
18. Hemrika, W.; Renirie, R.; Macedo-Ribeiro, S.; Messerschmidt, A.; Wever, R. J. Biol. Chem. 1999, 274, 23820-23827 10.1074/jbc.274.34.23820
19. ten Brink, H. B.; Tuynman, A.; Dekker, H. L.; Hemrika, W.; Izumi, Y.; Oshiro, T.; Schoemaker, H. E.; Wever, R. Inorg. Chem. 1998, 37, 6780-6784 10.1021/ic9806075
20. Fernández-Fueyo, E.; van Wingerden, M.; Renirie, R.; Wever, R.; Ni, Y.; Holtmann, D.; Hollmann, F. ChemCatChem 2015, 7, 4035 10.1002/cctc.201500862
21. van Schijndel, J. W. P. M.; Barnett, P.; Roelse, J.; Vollenbroek, E. G. M.; Wever, R. Eur. J. Biochem. 1994, 225, 151-157 10.1111/j.1432-1033.1994.00151.x
22. But, A.; Le Nôtre, J.; Scott, E. L.; Wever, R.; Sanders, J. P. M. ChemSusChem 2012, 5, 1199-1202 10.1002/cssc.201200098