ChemBioChem
10.1002/cbic.201600417
COMMUNICATION
[17] a) E. de Boer, R. Wever, J. Biol. Chem. 1988, 263, 12326-12332; b) R.
R. Everett, H. S. Soedjak, A. Butler, J. Biol. Chem. 1990, 265, 15671-
15679.
[18] H. S. Soedjak, A. Butler, Inorg. Chem. 1990, 29, 5015-5017.
[19] T. Ohshiro, W. Hemrika, T. Aibara, R. Wever, Y. Izumi, Phytochemistry
2002, 60, 595-601.
[20] a) G. E. Meister Winter, A. Butler, Biochemistry 1996, 35, 11805-11811;
b) H. S. Soedjak, J. V. Walker, A. Butler, Biochemistry 1995, 34, 12689-
12696.
Deutsche Bundesstiftung Umwelt for
a fellowship (grant
20015/400). We acknowledge the European Synchrotron
Radiation Facility for provision of synchrotron radiation facilities
and we would like to thank Dr. Bart van Laer for assistance in
using beamline ID23-1.
[21] D. J. Sheffield, T. Harry, A. J. Smith, L. J. Rogers, Phytochemistry
1992, 32, 21-26.
Keywords: vanadium • enzyme catalysis • protein structures •
[22] J. N. Carter, K. E. Beatty, M. T. Simpson, A. Butler, J. Inorg. Biochem.
2002, 91, 59-69.
halogenation • peroxidases
[23] a) E. Verhaeghe, D. Buisson, E. Zekri, C. Leblanc, P. Potin, Y.
Ambroise, Anal. Biochem. 2008, 379, 60-65; b) D. Wischang, J.
Hartung, Tetrahedron 2011, 67, 4048-4054.
[24] P. Barnett, W. Hemrika, H. L. Dekker, A. O. Muijsers, R. Renirie, R.
Wever, J. Biol. Chem. 1998, 273, 23381-23387.
[25] a) T.-N. Ernie Liu, T. M'Timkulu, J. Geigert, B. Wolf, S. L. Neidleman, D.
Silva, J. C. Hunter-Cevera, Biochem. Biophys. Res. Commun. 1987,
142, 329-333; b) J. W. van Schijndel, E. G. Vollenbroek, R. Wever,
Biochim. Biophys. Acta 1993, 1161, 249-256. c) W. Hemrika, R.
Renirie, S. Macedo-Ribeiro, A. Messerschmidt, R. Wever, J. Biol.
Chem. 1999, 274, 23820-23827. d) N. Tanaka, Z. Hasan, R. Wever,
Inorg. Chim. Acta 2003, 356, 288-296.
[1]
[2]
a) G. W. Gribble, Mar. Drugs 2015, 13, 4044-4136; b) R. Wever, M. A.
van der Horst, Dalton Trans. 2013, 42, 11778-11786; c) A. Butler, M.
Sandy, Nature 2009, 460, 848-854.
a) G. W. Gribble, Environ. Chem. 2015, 12, 396-405; b) D. O’Hagan, H.
Deng, Chem. Rev. 2015, 115, 634-649; c) G. W. Gribble, J. Chem.
Educ. 2004, 81, 1441-1449; d) G. W. Gribble, Chemosphere 2003, 52,
289-297; e) C. Wagner, M. El Omari, G. M. König, J. Nat. Prod. 2009,
72, 540-553; f) C. Paul, G. Pohnert, Nat. Prod. Rep. 2011, 28, 186-195.
For recent reviews on halogenations catalyzed by VHPOs see: a) V.
Weichold, D. Milbredt, K.-H. van Pée, Angew. Chem. 2016, 55, 6374-
6389; b) D. Wischang, O. Brücher, J. Hartung, Coord. Chem. Rev.
2011, 255, 2204-2217; c) J. M. Winter, B. S. Moore, J. Biol. Chem.
2009, 284, 18577-18581; d) C. S. Neumann, D. G. Fujimori, C. T.
Walsh, Chem. Biol. 2008, 15, 99-109; e) D. G. Fujimori, C. T. Walsh,
Curr. Op. Chem. Biol 2007, 11, 553-560; f) F. H. Vaillancourt, E. Yeh,
D. A. Vosburg, S. Garneau-Tsodikova, C. T. Walsh, Chem. Rev. 2006,
106, 3364-3378.
For selected, recent examples on halogenations catalyzed by VHPOs
see: a) E. Fernández-Fueyo, M. van Wingerden, R. Renirie, R. Wever,
Y. Ni, D. Holtmann, F. Hollmann, ChemCatChem 2015, 7, 4035-4038;
b) F. Sabuzi, E. Churakova, P. Galloni, R. Wever, F. Hollmann, B.
Floris, V. Conte, Eur. J. Inorg. Chem. 2015, 3519-3525; c) S. Diethelm,
R. Teufel, L. Kaysser, B. S. Moore, Angew. Chem. Int. Ed. 2014, 53,
11023-11026; d) R. Teufel, L. Kaysser, M. T. Villaume, S. Diethelm, M.
K. Carbullido, P. S. Baran, B. S. Moore, Angew. Chem. Int. Ed. 2014,
53, 11019-11022; e) D. Wischang, M. Radlow, J. Hartung, Dalton
Trans. 2013, 42, 11926-11940; f) M. Sandy, J. N. Carter-Franklin, J. D.
Martiny, A. Butler, Chem. Commun. 2011, 47, 12086-12088; g) P.
Bernhardt, T. Okino, J. M. Winter, A. Miyanaga, B. S. Moore, J. Am.
Chem. Soc. 2011, 133, 4268-4270.
[3]
[26] W. Hemrika, R. Renirie, S. Macedo-Ribeiro, A. Messerschmidt, R.
Wever, J. Biol. Chem. 1999, 274, 23820-23827.
[27] Although, to our knowledge, no halogenated secondary metabolites
have been isolated from A. marina until today, cyanobacteria are
responsible for the production of significant amounts of bromoform and
similar brominated compounds in the ocean. As an example see: R.
Wever, M. a. van der Horst, Dalton Trans. 2013, 42, 11778-11786.
[28] No reaction was observed if AmVHPO, KBr, or H2O2 was omitted.
[29] R. Kaur, M. P. Darokar, S. K. Chattopadhyay, V. Krishna, A. Ahmad,
Med. Chem. Res. 2013, 23, 2212-2217.
[4]
[5]
a) J. W. Van Schijndel, P. Barnett, J. Roelse, E. G. Vollenbroek, R.
Wever, Eur. J. Biochem. 1994, 225, 151-157; b) M. G. M. Tromp, G.
Olafsson, B. E. Krenn, R. Wever, Biochim. Biophys. Acta 1990, 1040,
192-198; c) E. E. Coupe, M. G. Smyth, A. P. Fosberry, R. M. Hall, J. A.
Littlechild, Protein Expr. Purif. 2007, 52, 265-272; d) E. de Boer, H.
Plat, M. G. Tromp, R. Wever, M. C. Franssen, H. C. van der Plas, E. M.
Meijer, H. E. Schoemaker, Biotechnol. Bioeng. 1987, 30, 607-610.
C,F bond formation can not proceed via an electrophilic mechanism as
the oxidation of fluoride is thermodynamically disfavored.
[6]
[7]
a) T. L. Johnson, B. Palenik, B. Brahamsha, J. Phycol. 2011, 47, 792-
801; b) T. L. Johnson, B. Brahamsha, B. Palenik, J. Mühle, Limnol.
Ocean. 2015, 60, 1823-1835.
[8]
[9]
S. F. Altschul, W. Gish, W. Miller, E. W. Myers, D. J. Lipman, J. Mol.
Biol. 1990, 215, 403-410.
E. Garcia-Rodriguez, T. Ohshiro, T. Aibara, Y. Izumi, J. Littlechild, J.
Biol. Inorg. Chem. 2005, 10, 275-282.
[10] E. Krissinel, K. Henrick, J. Mol. Biol. 2007, 372, 774-797.
[11] a) M. N. Isupov, A. R. Dalby, A. A. Brindley, Y. Izumi, T. Tanabe, G. N.
Murshudov, J. A. Littlechild, J. Mol. Biol. 2000, 299, 1035-1049; b) N.
Itoh, Y. Izumi, H. Yamada, J. Biol. Chem. 1987, 262, 11982-11987; c)
N. Itoh, Y. Izumi, H. Yamada, J. Biol. Chem. 1986, 261, 5194-5200; d)
C. Leblanc, H. Vilter, J. B. Fournier, L. Delage, P. Potin, E. Rebuffet, G.
Michel, P. L. Solari, M. C. Feiters, M. Czjzek, Coord. Chem. Rev. 2015,
301-302, 134-146; e) M. Weyand, H. J. Hecht, M. Kieß, M. F. Liaud, H.
Vilter, D. Schomburg, J. Mol. Biol. 1999, 293, 595-611; f) J. N. Carter-
Franklin, J. D. Parrish, R. A. Tschirret-Guth, R. D. Little, A. Butler, J.
Am. Chem. Soc. 2003, 125, 3688-3689.
[12] H. Miyashita, H. Ikemoto, N. Kurano, K. Adachi, M. Chihara, S. Miyachi,
Nature 1996, 383, 402-402.
[13] T. Cavalier-Smith, Biol. J. Linn. Soc. 1982, 17, 289-306.
[14] A. Messerschmidt, R. Wever, Proc. Natl. Acad. Sci. 1996, 93, 392-396.
[15] Z. Hasan, R. Renirie, R. Kerkman, H. J. Ruijssenaars, A. F. Hartog, R.
Wever, J. Biol. Chem. 2006, 281, 9738-9744.
[16] a) L. P. Hager, D. R. Morris, F. S. Brown, H. Eberwein, J. Biol. Chem.
1966, 241, 1769-1777; b) F. Björkstén, Eur. J. Biochem. 1968, 5, 133-
142.
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