Protection of a single-cysteine redox switch from oxidative destruction: On the functional role of sulfenyl amide formation in the redox-regulated enzyme PTP1B

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 2, 2010, Pages 444-447

  Sivaramakrishnan, Santhosh ^a   Cummings, Andrea H ^a   Gates, Kent S ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

Protein tyrosine phosphatase; Redox regulation; Sulfenic acid

Indexed keywords

AMIDE; CYSTEINE; DISULFIDE; MERCAPTOETHANOL; PROTEIN TYROSINE PHOSPHATASE 1B; SULFINIC ACID DERIVATIVE; THIOL; WATER;

AEROBIC METABOLISM; ARTICLE; CHEMICAL MODEL; ENZYME ACTIVE SITE; ENZYME REGULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OXIDATION; OXIDATION REDUCTION REACTION;

AMIDES; CYSTEINE; OXIDATION-REDUCTION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; SULFENIC ACIDS; SULFHYDRYL COMPOUNDS;

EID: 72249105280     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.001     Document Type: Article

References (38)

1. Autréaux B.D., and Toledano M.B. Nat. Rev. Mol. Cell Biol. 8 (2007) 813
2. Janssen-Heininger Y.M.W., Mossman B.T., Heintz N.H., Forman H.J., Kalyanaraman B., Finkel T., Stamler J.S., Rhee S.G., and van der Vliet A. Free Radical Biol. Med. 45 (2008) 1
3. Rhee S.G. Science 312 (2006) 1882
4. Poole L.B., Karplus P.A., and Claiborne A. Annu. Rev. Pharmacol. Toxicol. 44 (2004) 3325
5. Winterbourn C.C., and Hampton M.B. Free Radical Biol. Med. 45 (2008) 549
6. Brandes N., Schmitt S., and Jakob U. Antioxid. Redox Signal. 11 (2008) 997
7. Reddie K.G., and Carroll K.S. Curr. Opin. Chem. Biol. 12 (2008) 746
8. Jacob C., Holme A.L., and Fry F.H. Org. Biomol. Chem. 2 (2004) 1953
9. Turell L., Botti H., Carballal S., Ferrer-Sueta G., Souza J.M., Durán R., Freeman B.A., Radi R., and Alvarez B. Biochemistry 47 (2008) 358
10. Sohn J., and Rudolph J. Biochemistry 42 (2003) 10060
11. Chen C.-Y., Willard D., and Rudolph J. Biochemistry 48 (2009) 1399
12. Lee S.-R., Yang K.-S., Kwon J., Lee C., Jeong W., and Rhee S.G. J. Biol. Chem. 277 (2002) 20336
13. Tsai S.J., Sen U., Zhao L., Greenleaf W.B., Dasgupta J., Fiorillo E., Orrú V., Bottini N., and Chen X.S. Biochemistry 48 (2009) 4838
14. Kice J.L., and Rogers T.E. J. Am. Chem. Soc. 96 (1974) 8015
15. Tonks N.K. Nat. Rev. Cell. Biol. 7 (2006) 833
16. Denu J.M., and Tanner K.G. Biochemistry 37 (1998) 5633
17. Tonks N.K. Cell 121 (2005) 667
18. Mahedev K., Zilbering A., Zhu L., and Goldstein B.J. J. Biol. Chem. 276 (2001) 21938
19. Meng T.-C., Buckley D.A., Galic S., Tiganis T., and Tonks N.K. J. Biol. Chem. 279 (2004) 37716
20. Salmeen A., Anderson J.N., Myers M.P., Meng T.-C., Hinks J.A., Tonks N.K., and Barford D. Nature 423 (2003) 769
21. van Montfort R.L.M., Congreeve M., Tisi D., Carr R., and Jhoti H. Nature 423 (2003) 773
22. Sivaramakrishnan S., Keerthi K., and Gates K.S. J. Am. Chem. Soc. 127 (2005) 10830
23. Yang J., Groen A., Lemeer S., Jans A., Slijper M., Roe S.M., den Hertog J., and Barford D. Biochemistry 46 (2007) 709
24. Lee J.-W., Soonsanga S., and Helmann J.D. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 8743
25. Bender M.L., and Turnquest B.W. J. Am. Chem. Soc. 79 (1957) 1656
26. Breslow R. J. Am. Chem. Soc. 80 (1958) 3719
27. Westheimer F.H., and Bender M.L. J. Am. Chem. Soc. 84 (1962) 4908
28. Bruice T.C. Prog. Bioorg. Chem. 4 (1976) 1
29. Wennemers H., and Raines R.T. Curr. Opin. Chem. Biol. 12 (2008) 690
30. Pratt D.A., Pesavento R.P., and van der Donk W.A. Org. Lett. 7 (2005) 2735
31. + 254.0487, found 254.0493.
32. + 240.0694, found 240.0706.
33. Clarke V., and Cole E.R. Phosphorus, Sulfur Silicon 91 (1994) 45
34. For a mechanistic study on the hydrolysis of simple sulfinamides, see. Okuyama T., Lee J.P., and Kazunobu O. J. Am. Chem. Soc. 116 (1994) 6480
35. + 286.0749, found 286.0755.
36. Kice J.L., and Rogers T.E. J. Am. Chem. Soc. 96 (1974) 8009
37. Nagy P., and Ashby M.T. Chem. Res. Toxicol. 20 (2007) 1364
38. + 270.0436, found 270.0446.