Reductive metalation of cyclic and acyclic pseudopeptidic bis-disulfides and back conversion of the resulting diamidato/dithiolato complexes to bis-disulfides

Inorganic Chemistry

Volumn 49, Issue 18, 2010, Pages 8637-8644

  Desbenoi̧t, Nicolas ^a,b   Galardon, Erwan ^a   Frapart, Yves ^a   Tomas, Alain ^b   Artaud, Isabelle ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COPPER; DISULFIDE; IRON; ORGANOMETALLIC COMPOUND; PEPTIDOMIMETIC AGENT; SULFUR;

ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION;

AMIDES; COPPER; DISULFIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; IRON; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PEPTIDOMIMETICS; SULFUR;

EID: 77956496091     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101148c     Document Type: Article

References (40)

1. Nagashima, S., Nakasako, M., Dohmae, N., Tsujimura, M., Takio, K., Odaka, M., Yohda, M., Kamiya, N., and Endo, I. Nat. Struct. Biol. 1998, 5, 347-351
2. Miyanago, A., Fushinobu, S., Ito, K., and Wakagi, T. Biochem. Biophys. Res. Commun. 2001, 288, 1169-1174
3. Darnault, C., Volbeda, A., Kim, E. J., Legrand, P., de Verne, X., Lindahl, P. A., and Fontecilla-Camps, J. C. Nat. Struct. Biol. 2003, 10, 271-279
4. Doukov, T. I., Iverson, T. M., Seravalli, J., Ragsdale, S. W., and Drennan, C. L. Science 2002, 298, 567-572
5. Ganz, T. and Nemeth, E. Biochim. Biophys. Acta 2006, 1663, 690-699
6. Nemeth, E., Tuttle, M. S., Powelson, J., Vaughn, M. B., Donovan, A., Ward, D. M., Ganz, T., and Kaplan, J. Science 2004, 306, 2090-2093
7. Jordan, J. B., Poppe, L., Haniu, M., Arvedson, T., Syed, R., Li, V., Kohno, H., Helen Kim, H., Schnier, P. D., Miranda, L. P., Cheetham, J., and Sasu, B. J. J. Biol. Chem. 2009, 284, 24155-24167
8. Hunter, H. N., Fulton, D. B., Ganz, T., and Vogel, H. J. J. Biol. Chem. 2002, 277, 37597-37603
9. Farnaud, S., Rapisarda, C., Bui, T., Drake, A., Cammak, R., and Evans, R. W. Biochem. J. 2008, 413, 553-557
10. Farnaud, S., Patel, A., and Evans, R. W. Biometals 2006, 19, 527-533
11. Gerardi, G., Biasiotto, G., Santambrogio, P., Zanella, I., Ingrassia, R., Corrado, M., Cavadini, P., Derosas, M., Levi, S., and Aorosio, P. Blood Cells Mol. Dis. 2005, 35, 177-191
12. Bourlès, E., Alves de Sousa, R., Selkti, M., Tomas, A., and Artaud, I. Tetrahedron 2007, 63, 2466-2471
13. Grayson, E. J., Ward, S. J., Hall, A. L., Rendle, P. M., Gamblin, D. P., Andrei, S., Batsanov, A. S., and Davis, B. G. J. Org. Chem. 2005, 70, 9740-9754
14. Hanss, J. and Krüger, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2827-2830
15. Desbenoit, N., Galardon, E., Roussel, P., Artaud, I., and Tomas, A. J. Coord. Chem. 2009, 62, 2472-2479
16. Ottersen, T., Warner, L. G., and Seff, K. Inorg. Chem. 1974, 13, 1904-1911
17. Itoh, S., Nagagawa, M., and Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 4087-4088
18. Osako, T., Ueno, Y., and Itoh, S. Inorg. Chem. 2003, 42, 8087-8097
19. Frapart, Y.-M., Boussac, A., Anxolabehere-Mallard, E., Delroissse, M., Verlhac, J.-B., Blondin, G., Girerd, J.-J., Guilhem, J., cesario, M., Rutherford, A. W., and Lexa, D. J. Am. Chem. Soc. 1996, 118, 2669-2678
20. Innes, J. B. and G. W. Brudvig, G. W. Biochemistry 1989, 28, 1116-1125
21. Merdy, P., Guillon, E., Frapart, Y.-M., and Aplincourt, M. New J. Chem. 2003, 27, 577-582
22. Miyoshi, K., Sugiura, Y., Ishizu, K., Iitaka, Y., and Nakamura, H. J. Am. Chem. Soc. 1980, 102, 6130-6136
23. Chatel, S., Chauvin, A.-S., Tuchagues, J.-P., Leduc, P., Bill, E., Chottard, J.-C, Mansuy, D., and Artaud, I. Inorg. Chim. Acta 2002, 336, 19-28
24. Maelia, L., Millar, M., and Koch, S. A. Inorg. Chem. 1992, 31, 4594-4600
25. Millar, M., Lee, J. F., OSullivan, T., Koch, S. A., and Fikar, R. Inorg. Chim. Acta 1996, 243, 333-343
26. Galardon, E., Giorgi, M., and Artaud, I. Chem; Commun. 2004, 286-287
27. Tsai, F.-T., Chiou, S.-J., Tsai, M.-C., Huang, H.-W., Chang, M.-H., and Liaw, W.-F. Inorg. Chem. 2005, 44, 5872-5881
28. Fox, S., Stibrany, R. T., Potenza, J. A., Knapp, S., and Schugar, H. J. Inorg. Chem. 2000, 39, 4950-4961
29. Lyon, E. J., Musie, G., Reibenspies, J. H., and Darensbourg, M. Y. Inorg. Chem. 1998, 37, 6942-6946
30. Steinfeld, G., Lozan, V., Krüger, H.-J., and Kersting, B. Angew. Chem., Int. Ed. 2009, 48, 1954-1957
31. Alves de Sousa, R., Galardon, E., Rat, M., Giorgi, M., and Artaud, I. J. Inorg. Biochem. 2005, 99, 690-697
32. Gooda, M., Major, A., Nag-Chaughuri, J., and McGlynn, S. P. J. Am. Chem. Soc. 1961, 83, 4329-4333
33. Billard, T., Langlois, B. R., Large, S., Anker, D., Roidot, N., and Roure, P. J. Org. Chem. 1996, 61, 7545-7550
34. Doi, J. T., Luehr, G. W., and Musker, W. K. J. Org. Chem. 1985, 50, 5716-5719
35. Galardon, E., Tomas, A., Selkti, M., Roussel, P., and Artaud, I. Inorg. Chem. 2009, 48, 5921-5927
36. Alves de Sousa, R. and Artaud, I. Tetrahedron 2008, 64, 2198-2206
37. Bourlès, E., Alves de Sousa, R., Galardon, E., and Artaud, I. Angew. Chem., Int. Ed. 2005, 44, 6162-6165
38. Galardon, E., Bourlès, E., Artaud, I., Daran, J.-C., Roussel, P., and Tomas, A. Inorg. Chem. 2007, 46, 4515-4522
39. Field, L., Vanhorne, J. L., and Cunningham, L. W. J. Org. Chem. 1970, 35, 3267-3273
40. Block, E., Bentley, M. D., Davis, F. A., Douglass, I. B., and Lacadielb, J. A. J. Org. Chem. 1975, 40, 2770-2773