In the active-site cavity of vanadium haloperoxidases vanadate as the prosthetic group is solely fixed by one covalent bond to a histidine residue and embedded in a supramolecular environment of extensive hydrogen bonds. Structural aspects of relevant vanadium complexes with supramolecular interactions, including assemblies with chiral hosts, are presented. The importance of hydrogen-bonding relays is presented together with relevant examples. The reactivity of related functional mimics containing vanadium and molybdenum toward the oxidation of thioethers is described. Computational modeling based on density functional theory (DFT) is used for the investigation of model systems. The resulting implications for structure and function of vanadium haloperoxidases, including their substrate and cofactor specificity, are discussed.
Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
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- Online
- ISSN
- 1365-3075
Vanadium haloperoxidases as supramolecular hosts: Synthetic and computational models
Free Access
Keywords: DFT; haloperoxidases; hydrogen bonding; supramolecular assemblies; vanadium
Conference
International Symposium on Chemistry and Biological Chemistry of Vanadium, International Vanadium Symposium, V, Vanadium , 6th, Lisbon, Portugal, 2008-07-17–2008-07-19
References
- 1.
, D. C. Crans, J. J. Smee, E. Gaidamauskas, L. Yang. Chem. Rev. 104, 849 (2004).CrossrefGoogle Scholar
- 2.
(a) H. Sigel, A. E. Sigel (Eds.). Vanadium and its Role in Life, Vol. 31 of Metal Ions in Biological Systems, Marcel Dekker, New York (1995);Google Scholar
- 2.
, (b) K. H. Thompson, J. H. McNeill, C. Orvig. Chem. Rev. 99, 2561 (1999);CrossrefGoogle Scholar
- 2.
(c) K. Kustin, J. Costa Pessoa, D. C. Crans (Eds.). Vanadium: The Versatile Metal, ACS Symposium Series No. 974, American Chemical Society, Washington, DC (2007).Google Scholar
- 3.
, W. Plass. Angew. Chem., Int. Ed. 38, 909 (1999).CrossrefGoogle Scholar
- 4.
, W. Plass. Coord. Chem. Rev. 237, 205 (2003).CrossrefGoogle Scholar
- 5.
, H. Vilter. Phytochemistry 23, 1387 (1984).CrossrefGoogle Scholar
- 6.
, A. Messerschmidt, R. Wever. Proc. Natl. Acad. Sci. USA 93, 392 (1996).CrossrefGoogle Scholar
- 7.
, M. Weyand, H. J. Hecht, M. Kiess, M. F. Liaud, H. Vilter, D. Schomburg. J. Mol. Biol. 293, 595 (1999).CrossrefGoogle Scholar
- 8.
, M. N. Isupov, A. R. Dalby, A. A. Brindley, Y. Izumi, T. Tanabe, G. N. Murshudov, J. A. Littlechild. J. Mol. Biol. 299, 1035 (2000).CrossrefGoogle Scholar
- 9.
, A. Messerschmidt, R. Wever. Inorg. Chim. Acta 273, 160 (1998).CrossrefGoogle Scholar
- 10.
, (a) G. W. Gribble. Acc. Chem. Res. 31, 141 (1998);CrossrefGoogle Scholar
- 10.
(b) R. Wever, W. Hemrika. In Handbook of Metalloproteins, Vol. 2, A. Messerschmidt, R. Huber, T. Poulos, K. Wieghardt (Eds.), pp. 14171428, John Wiley, Chichester (2001).Google Scholar
- 11.
, (a) M. Andersson, A. Willetts, S. Allenmark. J. Org. Chem. 62, 8455 (1997);CrossrefGoogle Scholar
- 11.
, (b) H. B. ten Brink, H. E. Schoemaker, R. Wever. Eur. J. Biochem. 268, 132 (2001).CrossrefGoogle Scholar
- 12.
, (a) R. Renirie, W. Hemrika, S. R. Piersma, R. Wever. Biochemistry 39, 1133 (2000);CrossrefGoogle Scholar
- 12.
, (b) C. Kimblin, X. H. Bu, A. Butler. Inorg. Chem. 41, 161 (2002);CrossrefGoogle Scholar
- 12.
, (c) N. Tanaka, Z. Hasan, R. Wever. Inorg. Chim. Acta 356, 288 (2003).CrossrefGoogle Scholar
- 13.
, Z. Hasan, R. Renirie, R. Kerkman, H. J. Ruijssenaars, A. F. Hartog, R. Wever. J. Biol. Chem. 281, 9738 (2006).CrossrefGoogle Scholar
- 14.
, M. Bangesh, W. Plass. J. Mol. Struct. Theochem. 725, 163 (2005).CrossrefGoogle Scholar
- 15.
, (a) J. Y. Kravitz, V. L. Pecoraro. Pure Appl. Chem. 77, 1595 (2005);CrossrefGoogle Scholar
- 15.
(b) C. Schneider, G. Zampella, L. De Gioa, V. L. Pecoraro. In Vanadium: The Versatile Metal, ACS Symposium Series No. 974, K. Kustin, J. Costa Pessoa, D. C. Crans (Eds.), p. 148, American Chemical Society, Washington, DC (2007).Google Scholar
- 16.
W. Plass, M. Bangesh, S. Nica, A. Buchholz. In Vanadium: The Versatile Metal, ACS Symposium Series No. 974, K. Kustin, J. Costa Pessoa, D. C. Crans (Eds.), p. 163, American Chemical Society, Washington, DC (2007).Google Scholar
- 17.
, S. Raugei, P. Carloni. J. Phys. Chem. B 110, 3747 (2006).CrossrefGoogle Scholar
- 18.
J. Littlechild, E. Garcia-Rodriguez, E. Coupe, A. Watts, M. Isupov. In Vanadium: The Versatile Metal, ACS Symposium Series No. 974, K. Kustin, J. Costa Pessoa, D. C. Crans (Eds.), p. 136, American Chemical Society, Washington, DC (2007).Google Scholar
- 19.
, M. J. Clague, A. Butler. J. Am. Chem. Soc. 117, 3415 (1995).CrossrefGoogle Scholar
- 20.
, (a) V. Conte, F. Di Furia, S. Moro. J. Phys. Org. Chem. 9, 329 (1996);CrossrefGoogle Scholar
- 20.
, (b) G. E. Meister, A. Butler. Inorg. Chem. 33, 3269 (1994);CrossrefGoogle Scholar
- 20.
, (c) A. F. Ghiron, R. C. Thompson. Inorg. Chem. 29, 4457 (1990).CrossrefGoogle Scholar
- 21.
A. Butler, A. H. Baldwin. Struct. Bonding 89, 109 (1997).Google Scholar
- 22.
, K. Ishikawa, Y. Mihara, K. Gondoh, E. Suzuki, Y. Asano. EMBO J. 19, 2412 (2000).CrossrefGoogle Scholar
- 23.
, (a) W. Plass, A. Pohlmann, H.-P. Yozgatli. J. Inorg. Biochem. 80, 181 (2000);CrossrefGoogle Scholar
- 23.
, (b) W. Plass, H. P. Yozgatli. Z. Anorg. Allg. Chem. 629, 65 (2003).CrossrefGoogle Scholar
- 24.
, (a) A. Pohlmann, W. Plass. J. Inorg. Biochem. 86, 381 (2001);CrossrefGoogle Scholar
- 24.
, (b) S. Nica, A. Pohlmann, W. Plass. Eur. J. Inorg. Chem. 2032 (2005);CrossrefGoogle Scholar
- 24.
, (c) A. Pohlmann, S. Nica, T. K. K. Luong, W. Plass. Inorg. Chem. Commun. 8, 289 (2005);CrossrefGoogle Scholar
- 24.
, (d) S. Nica, M. Rudolph, H. Gorls, W. Plass. Inorg. Chim. Acta 360, 1743 (2007);CrossrefGoogle Scholar
- 24.
, (e) S. Nica, A. Buchholz, M. Rudolph, A. Schweitzer, M. Wachtler, H. Breitzke, G. Buntkowsky, W. Plass. Eur. J. Inorg. Chem. 2350 (2008).CrossrefGoogle Scholar
- 25.
, J. Becher, I. Seidel, W. Plass, D. Klemm. Tetrahedron 62, 5675 (2006).CrossrefGoogle Scholar
- 26.
, I. Lippold, H. Gorls, W. Plass. Eur. J. Inorg. Chem. 1487 (2007).CrossrefGoogle Scholar
- 27.
, (a) W. Plass. Z. Anorg. Allg. Chem. 623, 461 (1997);CrossrefGoogle Scholar
- 27.
, (b) W. Plass. Eur. J. Inorg. Chem. 799 (1998).CrossrefGoogle Scholar
- 28.
A. Messerschmidt, L. Prade, R. Wever. Biol. Chem. 378, 309 (1997).Google Scholar
- 29.
, M. Mancka, W. Plass. Inorg. Chem. Commun. 10, 677 (2007).CrossrefGoogle Scholar
- 30.
, I. Lippold, J. Becher, D. Klemm, W. Plass. J. Mol. Catal. A: Chem. 299, 12 (2008).CrossrefGoogle Scholar
- 31.
, I. Lippold, K. Vlay, H. Gorls, W. Plass. J. Inorg. Biochem. 103, 480 (2009).CrossrefGoogle Scholar
- 32.
, (a) V. Conte, O. Bortolini, S. Carraro, S. Moro. J. Inorg. Biochem. 80, 41 (2000);CrossrefGoogle Scholar
- 32.
(b) O. Bortolini, M. Carraro, V. Conte, S. Moro. Eur. J. Biochem. 42 (2003).Google Scholar
- 33.
, G. Zampella, J. Y. Kravitz, C. E. Webster, P. Fantucci, M. B. Hall, H. A. Carlson, V. L. Pecoraro, L. De Gioia. Inorg. Chem. 43, 4127 (2004).CrossrefGoogle Scholar
- 34.
, G. Zampella, P. Fantucci, V. L. Pecoraro, L. De Gioia. J. Am. Chem. Soc. 127, 953 (2005).CrossrefGoogle Scholar
- 35.
, J. Y. Kravitz, V. L. Pecoraro, H. A. Carlson. J. Chem. Theory Comput. 1, 1265 (2005).CrossrefGoogle Scholar
- 36.
, Y. Zhang, J. A. Gascon. J. Inorg. Biochem. 102, 1684 (2008).CrossrefGoogle Scholar
- 37.
, M. P. Waller, M. Buhl, K. R. Geethalakshmi, D. Wang, W. Thiel. Chem.Eur. J. 13, 4723 (2007).CrossrefGoogle Scholar
- 38.
D. Geibig, R. Wilcken, M. Bangesh, W. Plass. NIC Series 39, 71 (2008).Google Scholar
About the article
Published Online: 2009-06-29
Published in Print: 2009-06-30
Citation Information: Pure and Applied Chemistry, Volume 81, Issue 7, Pages 1229–1239, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-08-10-19.
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