Isolation of a Se-nitrososelenol: A new class of reactive nitrogen species relevant to protein Se-nitrosation

Journal of the American Chemical Society

Volumn 126, Issue 41, 2004, Pages 13238-13239

  Shimada, Keiichi ^a   Goto, Kei ^a   Kawashima, Takayuki ^a   Takagi, Nozomi ^b   Choe, Yoong Kee ^b   Nagase, Shigeru ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NITRIC OXIDE; NITROSO DERIVATIVE; NITROSOSELENOL; REACTIVE NITROGEN SPECIES; SELENIUM DERIVATIVE; SELENOCYSTEINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; NITROSATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CRYSTALLOGRAPHY, X-RAY; ENZYME ACTIVATION; GLUTATHIONE PEROXIDASE; MOLECULAR STRUCTURE; NITRIC OXIDE; NITROSATION; NITROSO COMPOUNDS; S-NITROSOGLUTATHIONE; SELENIUM COMPOUNDS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 6044233336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0457009     Document Type: Article

References (20)

1. Moncada, S.; Palmer, R. M.; Higgs, E. A. Pharmacol Rev. 1991, 43, 109.
2. Nathan, C.; Xie, Q. Cell 1994, 78, 915.
3. Myers, P. R.; Minor, R. L.; Guerra, R.; Bates, J. N.; Harrison, D. G. Nature 1990, 345, 161.
4. Stamler, J. S.; Simon, D. I.; Osborne, J. A.; Mullins, M. E.; Jaraki, O.; Michel, T.; Singel, D. J.; Loscalzo, J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 444.
5. Freedman, J. E.; Frei, B.; Welch, G. N.; Loscalzo, J. J. Clin. Invest. 1995, 96, 394.
6. Asahi, M.; Fujii, J.; Suzuki, K.; Seo, H. G.; Kuzuya, T.; Hori, M.; Tada, M.; Fujii, S.; Taniguchi, N. J. Biol. Chem. 1995, 270, 21035.
7. Asahi, M.; Fujii, J.; Takao, T.; Kuzuya, T.; Hori, M.; Shimonishi, Y.; Taniguchi, N. J. Biol. Chem. 1997, 272, 19152.
8. Igarashi, J.; Nishida, M.; Hoshida, S.; Yamashita, N.; Kosaka, H.; Hori, M.; Kuzuya, T.; Tada, M. Am. J. Physiol. 1998, 274, C245.
9. Fujii, J.; Taniguchi, N. Free Radical Res. 1999, 31, 301.
10. Koh, Y. H.; Suzuki, K.; Che, W.; Park, Y. S.; Miyamoto, Y.; Higashiyama, S.; Taniguchi, N. FASEB J. 2001, 15, 1472.
11. Dobashi, K.; Asayama, K.; Nakane, T.; Kodera, K.; Hayashibe, H.; Nakazawa, S. Free Radical Res. 2001, 35, 319.
12. 3CSeH, where the generation of the corresponding Se-nitrososelenol was suggested by the IR spectrum at -78 °C, although the product underwent decomposition at temperatures above -78 °C: Wismach, C.; du Mont, W.-W.; Jones, P. G.; Ernst, L.; Papke, U.; Mugesh, G.; Kaim, W.; Wanner, M.; Becker, K. D. Angew. Chem., Int. Ed. 2004, 43, 3970.
13. Goto, K.; Hino, Y.; Kawashima, T.; Kaminaga, M.; Yano, E.; Yamamoto, G.; Takagi, N.; Nagase, S. Tetrahedron Lett. 2000, 41, 8479.
14. Goto, K.; Hino, Y.; Takahashi, Y.; Kawashima, T.; Yamamoto, G.; Takagi, N.; Nagase, S. Chem. Lett. 2001, 1204.
15. Goto, K.; Yamamoto, G.; Tan, B.; Okazaki, R. Tetrahedron Lett. 2001, 42, 4875.
16. See Supporting Information for the details of the synthetic procedures and spectral data of 1, 2, and 4 as well as the crystallographic data of 2.
17. All calculations were performed using the Gaussian 98 program (Gaussian Inc., Pittsburgh, PA, 1998).
18. Itoh, M.; Takenaka, K.; Okazaki, R.; Takeda, N.; Tokitoh, N. Chem. Lett. 2001, 1206.
19. An alternative pathway which includes a selenenic acid (RSeOH) instead of a Se-nitrososelenol was also suggested in ref 7.
20. Selenenyl sulfide 4 is not reduced by DTT under the conditions where Se-nitrososelenol 2 is reduced to selenol 1.