Pure Appl. Chem., 2009, Vol. 81, No. 7, pp. 1251-1264
http://dx.doi.org/10.1351/PAC-CON-08-09-01
Published online 2009-06-29
On the reactivity of bromoperoxidase I (Ascophyllum nodosum) in buffered organic media: Formation of carbon bromine bonds
References
- 1. R. Sander, W. C. Keene, A. A. P. Pszenny, R. Arimoto, G. P. Ayers, E. Baboukas, J. M. Cainey, P. J. Crutzen, R. A. Duce, G. Honninger, B. J. Huebert, W. Maenhaut, N. Mihalopoulos, V. C. Turekian, R. Van Dingenen. Atmos. Chem. Phys. 3, 1301 (2003).
- 2. H. Herrmann, Z. Majdik, B. Ervens, D. Weise. Chemosphere 52, 485 (2003). (http://dx.doi.org/10.1016/S0045-6535(03)00202-9)
- 3. A. Butler. Coord. Chem. Rev. 187, 17 (1999). (http://dx.doi.org/10.1016/S0010-8545(99)00033-8)
- 4. Compounds with One Saturated Carbon-Heteroatom Bond: Chlorine, Bromine, Iodine, Science of Syntheses, Vol. 35, Chap. 2, E. Schaumann (Ed.), Thieme-Verlag, Stuttgart (2006).
- 5. A. Gastaminza, H. M. Gilow, J. H. Ridd. J. Chem. Soc., Chem. Commun. 130 (1972). (http://dx.doi.org/10.1039/c39720000130)
- 6. O. A. Sadygov, Kh. M. Alimardanov, Ch. A. Chalabiev. Russ. J. Org. Chem. 41, 1631 (2005). (http://dx.doi.org/10.1007/s11178-006-0010-3)
- 7. S. L. Neidleman, J. Geigert. Biohalogenation. Principles, Basic Roles, and Applications, Ellis Horwood, Chichester (1986).
- 8. J. W. Blunt, B. R. Copp, W. P. Hu, M. H. G. Munro, P. T. Northcote, M. R. Prinsep. Nat. Prod. Rep. 25, 35 (2008). (http://dx.doi.org/10.1039/b701534h)
- 9. G. W. Gribble. Chemosphere 52, 289 (2003). (http://dx.doi.org/10.1016/S0045-6535(03)00207-8)
- 10. A. Peuner, V. J. Paul, P. J. Scheuer. Tetrahedron 45, 617 (1989). (http://dx.doi.org/10.1016/0040-4020(89)80089-4)
- 11. T. Kusumi, H. Uchida, Y. Inouye, M. Ishitsuka, H. Yamamoto H. Kakisawa. J. Org. Chem. 52, 4597 (1987). (http://dx.doi.org/10.1021/jo00229a029)
- 12. G. Guella, F. Pietra. Helv. Chim. Acta 83, 2946 (2000). (http://dx.doi.org/10.1002/1522-2675(20001108)83:11<2946::AID-HLCA2946>3.0.CO;2-2)
- 13. N. K. Utkina, S. A. Fedoreyev, S. G. Ilyin, M. Yu. Antipin. Russ. Chem. Bull. 47, 2292 (1998). (http://dx.doi.org/10.1007/BF02494298)
- 14. O. Maas, P. G. Hiebert. J. Am. Chem. Soc. 46, 290 (1924). (http://dx.doi.org/10.1021/ja01667a005)
- 15. C. W. Jones. Applications of Hydrogen Peroxide and Derivatives, J. H. Clark (Series Ed.), RSC Clean Technology Monographs, Cambridge (1999).
- 16. H. Vilter, K.-W. Glombitza, A. Grawe. Bot. Marina 26, 331 (1983).
- 17. H. Vilter. Phytochemistry 23, 1387 (1984). (http://dx.doi.org/10.1016/S0031-9422(00)80471-9)
- 18. H. Vilter. Metal Ions in Biological Systems, Vol. 31, Vanadium and its Role in Life, H. Sigel, A. Sigel (Eds.), Chap. 10, Marcel Dekker, New York (1995).
- 19. A. Butler, J. V. Walker. Chem. Rev. 93, 1937 (1993). (http://dx.doi.org/10.1021/cr00021a014)
- 20. R. Wever, H. Plat, E. de Boer. Biochim. Biophys. Acta 830, 181 (1985).
- 21. D. Rehder. Bioinorganic Vanadium Chemistry, Wiley-VCH, Weinheim (2008). (http://dx.doi.org/10.1002/9780470994429)
- 22. E. de Boer, H. Plat, M. G. M. Tromp, R. Wever, M. C. R. Franssen, H. C. van der Plas, E. M. Meijer, H. E. Schoemaker. Biotechnol. Bioeng. 30, 607 (1987). (http://dx.doi.org/10.1002/bit.260300504)
- 23. M. Weynand, H.-J. Hecht, M. Kiess, M.-F. Liaud, H. Vilter, D. Schomburg. J. Mol. Biol. 293, 595 (1999). (http://dx.doi.org/10.1006/jmbi.1999.3179)
- 24. A. Butler, J. N. Carter-Franklin. Nat. Prod. Rep. 21, 180 (2004). (http://dx.doi.org/10.1039/b302337k)
- 25. G. E. Meister, A. Butler. Inorg. Chem. 33, 3269 (1994). (http://dx.doi.org/10.1021/ic00093a013)
- 26. M. G. M. Tromp, G. Olafsson, B. E. Krenn, R. Wever. Biochim. Biophys. Acta 1040, 192 (1990).
- 27. H. Dau, J. Dittmer, M. Epple, J. Hanss, E. Kiss, D. Rehder, C. Schulzke, H. Vilter. FEBS Lett. 457, 237 (1999). (http://dx.doi.org/10.1016/S0014-5793(99)01045-5)
- 28. V. Conte, F. DiFuria, S. Moro. J. Mol. Catal. A 120, 93 (1997). (http://dx.doi.org/10.1016/S1381-1169(96)00435-9)
- 29. G. J. Colpas, B. J. Hamstra, J. W. Kampf, V. L. Pecoraro. J. Am. Chem. Soc. 118, 3469 (1996). (http://dx.doi.org/10.1021/ja953791r)
- 30. V. R. Hedge, G. C. G. Pais, R. Kumar, P. Kumar, B. Pandey. J. Chem. Res. (S) 62 (1996).
- 31. M. J. Clague, N. L. Keder, A. Butler. Inorg. Chem. 32, 4754 (1993). (http://dx.doi.org/10.1021/ic00074a017)
- 32. M. Greb, J. Hartung, F. Kohler, K. ?pehar, R. Kluge, R. Csuk. Eur. J. Org. Chem. 3799 (2004).
- 33. J. Hartung, M. Greb. Tetrahedron Lett. 44, 6091 (2003). (http://dx.doi.org/10.1016/S0040-4039(03)01468-0)
- 34. J. Hartung, O. Brucher, D. Hach, H. Schulz, H. Vilter, G. Ruick. Phytochemistry 69, 2826 (2008). (http://dx.doi.org/10.1016/j.phytochem.2008.09.004)
- 35. H. Vilter. Meth. Enzymol. 228, 665 (1994). (http://dx.doi.org/10.1016/0076-6879(94)28067-3)
- 36. S. Drees, M. Greb, J. Hartung, P. Schmidt. Peroxide Chemistry, W. Adam (Ed.), Chap. 5.2, Wiley-VCH, Weinheim (2000).
- 37. O. Bortolini, M. Carraro, V. Conte, S. Moro. Eur. J. Inorg. Chem. 1489 (1999). (http://dx.doi.org/10.1002/(SICI)1099-0682(199909)1999:9<1489::AID-EJIC1489>3.0.CO;2-X)
- 38. W. A. Waters. J. Chem. Soc. 727 (1948). (http://dx.doi.org/10.1039/jr9480000727)
- 39. P. D. P. de la Mare, C. A. Vernon. J. Chem. Soc. 1764 (1951). (http://dx.doi.org/10.1039/jr9510001764)
- 40. D. Rehder. In Vanadium in Biological Systems, D. Chasteen (Ed.), Chap. 10, Kluwer Academic, Dordrecht (1990).
- 41. M. Greb. Diploma Thesis, Universitat Wurzburg, Germany (2000).
- 42. K. Hafner, H. Patzelt, H. Kaiser. Liebigs Ann. Chem. 626, 24 (1962).
- 43. M. C. R. Franssen, J. D. Jansma, H. C. van der Plas, E. de Boer, R. Wever. Bioorg. Chem. 16, 352 (1988). (http://dx.doi.org/10.1016/0045-2068(88)90021-1)
- 44. J. S. Martinze, G. L. Carroll, R. A. Tschirret-Guth, G. Altenhoff, R. D. Little, A. Butler. J. Am. Chem. Soc. 123, 3289 (2001). (http://dx.doi.org/10.1021/ja004176c)
- 45. A. W. Francis. J. Am. Chem. Soc. 47, 2340 (1925). (http://dx.doi.org/10.1021/ja01686a011)
- 46. F. Kohler. Diplomarbeit, Universitat Wurzburg, Germany (2001).
- 47. A. K. Gupta, R. J. Kazlauskas. Tetrahedron: Asymmetry 4, 879 (1993). (http://dx.doi.org/10.1016/S0957-4166(00)80126-3)
- 48. H. Sharghi, H. Maeimi. Bull. Chem. Soc. Jpn. 72, 1525 (1999). (http://dx.doi.org/10.1246/bcsj.72.1525)
- 49. H. Hoenig, P. Seufer-Wasserthal. Synthesis 1137 (1990). (http://dx.doi.org/10.1055/s-1990-27115)
- 50. M. Chini, P. Crotti, C. Gardelli, F. Macchia. Tetrahedron 48, 3805 (1992). (http://dx.doi.org/10.1016/S0040-4020(01)92271-9)
- 51. G. Cardillo, M. Orena. Tetrahedron 46, 3321 (1990). (http://dx.doi.org/10.1016/S0040-4020(01)81510-6)
- 52. P. A. Bartlett. Asymmetric Synthesis, J. D. Morrison (Ed.), 3, 411, Academic Press, New York (1984).
- 53. M. Greb. Ph.D. Thesis, Universitat Wurzburg, Germany (2004).