Selenium and sulfur in exchange reactions: A comparative study

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6696-6699

  Steinmann, Daniel ^a,b   Nauser, Thomas ^a   Koppenol, Willem H ^a  

^a LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPARATIVE STUDIES; CYSTAMINE; CYSTEAMINE; ELECTROPHILES; EXCHANGE REACTION; LEAVING GROUPS; ORDERS OF MAGNITUDE; SELENIDES; SELENOCYSTAMINE;

SELENIUM; SELENIUM COMPOUNDS; SULFUR;

RATE CONSTANTS;

CYSTAMINE; CYSTEAMINE DERIVATIVE; CYSTEINE; HEMISELENOCYSTAMINE; NUCLEOPHILE; SELENIDE; SELENIUM; SELENOCYSTAMINE; SELENOCYSTINE; SULFIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; THERMODYNAMICS;

CYSTAMINE; CYSTEAMINE; MOLECULAR STRUCTURE; SELENIUM; SULFUR;

EID: 77957132219     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1011569     Document Type: Article

References (35)

1. ox, hemiselenocystamine; GPx, glutathione peroxidases; bis-tris, 2-[bis(2-hydroxyethyl)amino]-2- (hydroxymethyl)propane-1,3-diol; hepes, 4-(2-hydroxyethyl)-1- piperazineethanesulfonic acid; mops, 3-(N -morpholino)propanesulfonic acid.
2. Kryukov, G. V.; Castellano, S.; Novoselov, S. V.; Lobanov, A. V.; Zehtab, O.; Guigó, R.; Gladyshev, V. N. Science 2003, 300, 1439-1443
3. Gromer, S.; Eubel, J. K.; Lee, B. L.; Jacob, J. Cell. Mol. Life Sci. 2005, 62, 2414-2437
4. Huber, R. E.; Criddle, R. S. Arch. Biochem. Biophys. 1967, 122, 164-173
5. CRC Handbook of Chemistry and Physics; 87 th ed.; CRC Press: Boca Raton, 2006.
6. Perrin, D. D.; Sayce, I. G. J. Chem. Soc. A 1968, 53
7. Fomenko, D. E.; Xing, W.; Adair, B. M.; Thomas, D. J.; Gladyshev, V. N. Science 2007, 315, 387-389
8. Aumann, K. D.; Bedorf, N.; Brigelius-Flohé, R.; Schomburg, D.; Flohé, L. Biomed. Environ. Sci. 1997, 10, 136-155
9. Kim, H. Y.; Gladyshev, V. N. PLoS Biol. 2005, 3, 2080-2089
10. Zhong, L.; Arnér, E. S. J.; Holmgren, A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 5854-5859
11. Cheng, Q.; Sandalova, T.; Lindqvist, Y.; Arnér, E. S. J. J. Biol. Chem. 2009, 284, 3998-4008
12. Dickson, R. C.; Tappel, A. L. Arch. Biochem. Biophys. 1969, 130, 547-550
13. Kice, J. L.; Slebocka-Tilk, H. J. Am. Chem. Soc. 1982, 104, 7123-7130
14. Singh, R.; Kats, L. Anal. Biochem. 1995, 232, 86-91
15. Metanis, N.; Keinan, E.; Dawson, P. E. J. Am. Chem. Soc. 2006, 128, 16684-16691
16. Beld, J.; Woycechowsky, K. J.; Hilvert, D. Biochemistry 2007, 46, 5382-5390
17. Figueroa, J. S.; Yurkerwich, K.; Melnick, J.; Buccella, D.; Parkin, G. Inorg. Chem. 2007, 46, 9234-9244
18. Pleasants, J. C.; Guo, W; Rabenstein, D. L. J. Am. Chem. Soc. 1989, 111, 6553-6558
19. Singh, R.; Whitesides, G. M. J. Org. Chem. 1991, 56, 6931-6933
20. Bachrach, S. M.; Demoin, D. W.; Luk, M.; Miller, J. V. J. Phys. Chem. A 2004, 108, 4040-4046
21. Lees, W. J.; Whitesides, G. M. J. Org. Chem. 1993, 58, 642-647
22. Arnold, A. P.; Tan, K. S.; Rabenstein, D. L. Inorg. Chem. 1986, 25, 2433-2437
23. Nauser, T.; Dockheer, S.; Kissner, R.; Koppenol, W. H. Biochemistry 2006, 45, 6038-6043
24. Barton, J. P.; Packer, J. E.; Sims, R. J. J. Chem. Soc., Perkin Trans. 2 1973, 1547-1549
25. Winterbourn, C. C.; Metodiewa, D. Free Radical Biol. Med. 1999, 27, 322-328
26. Prütz, W. A. Z. Naturforsch., C: Biosci. 1995, 50, 209-219
27. Gancarz, R. A.; Kice, J. L. J. Org. Chem. 1981, 46, 4899-4906
28. Tosatto, S. C. E.; Bosello, V.; Fogolari, F.; Mauri, P.; Roveri, A.; Toppo, S.; Flohé, L.; Ursini, F.; Maiorino, M. Antioxid. Redox Signaling 2008, 10, 1515-1525
29. Huang, H. H.; Arscott, L. D.; Ballou, D. P.; Williams, C. H. Biochemistry 2008, 47, 1721-1731
30. Maiorino, M.; Ursini, F.; Bosello, V.; Toppo, S.; Tosatto, S. C. E.; Mauri, P.; Becker, K.;'Roveri, A.; Bulato, C.; Benazzi, L.; De Palma, A.; Flohé, L. J. Mol. Biol. 2007, 365, 1033-1046
31. Ursini, F.; Maiorino, M.; Gregolin, C. Biochim. Biophys. Acta 1985, 839, 62-70
32. Peskin, A. V.; Low, F. M.; Paton, L. N.; Maghzal, G. J.; Hampton, M. B.; Winterbourn, C. C. J. Biol. Chem. 2007, 282, 11885-11892
33. Flohé, L.; Loschen, G.; Eichele, E.; Günzler, W. A. Hoppe-Seylers Z. Physiol. Chem. 1972, 353, 987-999
34. Eckenroth, B. E.; Rould, M. A.; Hondal, R. J.; Everse, S. J. Biochemistry 2007, 46, 4694-4705
35. Maeder, M.; Zuberbühler, A. D. Anal. Chem. 1990, 62, 2220-2224