Regio- and enantioselectivities in epoxide conjugations are modulated by residue 210 in Mu class glutathione transferases

Protein Engineering, Design and Selection

Volumn 18, Issue 12, 2005, Pages 607-616

  Ivarsson, Ylva ^a   Mannervik, Bengt ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Epoxide; Glutathione transferase; Selectivity; Stilbene oxide; Styrene oxide

Indexed keywords

BIOCHEMISTRY; CATALYSIS; CHEMICAL MODIFICATION; ISOMERS; STEREOCHEMISTRY; STYRENE;

EPOXIDE; GLUTATHIONE TRANSFERASE (GST); SELECTIVITY; STILBENE OXIDE; STYRENE OXIDE;

ENZYMES;

EPOXIDE; GLUTATHIONE; GLUTATHIONE TRANSFERASE M1; HYDROXYL GROUP; SERINE; STILBENE; STILBENE OXIDE; STYRENE; STYRENE OXIDE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME ENGINEERING; ENZYME MODIFICATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ISOMER; PRIORITY JOURNAL; SEQUENCE HOMOLOGY; STEREOCHEMISTRY;

AMINO ACID SUBSTITUTION; CATALYSIS; EPOXY COMPOUNDS; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HUMANS; KINETICS; MODELS, MOLECULAR; MUTATION; SERINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THREONINE;

EID: 27944441021     PISSN: 17410126     EISSN: 17410134     Source Type: Journal    
DOI: 10.1093/protein/gzi064     Document Type: Article

References (40)

1. Aharoni,A., Gaidkov,L., Khersonsky,O., McQ Gould,S., Roodvelt,C. and Tawfik,D.S. (2005) Nat. Genet., 37, 73-76.
2. Armstrong,R.N. (1997) Chem. Res. Toxicol., 10, 2-18.
3. Bazelyansky,M., Robey,E. and Kirsch,J.F. (1986) Biochemistry, 25, 125-130.
4. Blacklow,S.C., Raines,R.T., Lim,W.A., Zamore P.D. and Knowles,J.R. (1988) Biochemistry, 27, 1158-1167.
5. Bogaards,J.J., Venekamp,J.C. and van Bladeren,P.J. (1997) Chem. Res. Toxicol., 10, 310-317.
6. Boyland,E. and Williams,K. (1965) Biochem. J., 94, 190-197.
7. Buening,M.K., Wislocki,P.G., Levin,W., Yagi,H., Thakker,D.R., Akagi H., Koreeda,M., Jerina,D.M. and Conney,A.H. (1978) Proc. Natl Acad. Sci. USA, 75, 5358-5361.
8. Cameron,A.D., Sinning,I., L'Hermite,G., Olin,B., Board,P.G., Mannervik,B. and Jones,T.A. (1995) Structure, 3, 717-727.
9. Codreanu,S.G., Ladner,J.E., Xiao,G., Stourman,N.V., Hachey,D.L., Gilliland,G.L. and Armstrong,R.N. (2002) Biochemistry, 41, 15161-15172.
10. deSmidt,P.C., McCarrick,M.A., Darnow,J.N., Mervic,M. and Armstrong,R.N. (1987) Biochem. Int., 14, 401-408.
11. Dostal,L.A., Guthenberg,C., Mannervik,B. and Bond,J.R. (1988) Drug. Metab. Dispos., 16, 420-424.
12. Fersht,A. (1999) Structure and Mechanism in Protein Science: a Guide to Enzyme Catalysis and Protein Folding. Freeman, New York.
13. Guengerich,F.P. (2003) J. Biochem. Mol. Biol., 36, 20-27.
14. Guengerich,F.P. et al. (1996) Adv. Exp. Med. Biol., 387, 7-15.
15. Guha,M.K., Vander Jagt,D.L. and Creighton,D.J. (1988) Biochemistry, 27, 8818-8822.
16. Hansson,L.O., Bolton-Grob,R., Widersten,M. and Mannervik,B. (1999) Protein Sci., 8, 2742-2750.
17. Hayakawa,T., Udenfriend,S., Yagi,H. and Jerina,D.M. (1975) Arch. Biochem. Biophys., 170, 438-451.
18. Hernandez,O., Bhatia,A.V. and Walker,M. (1983) J. Liq. Chromatogr., 6, 1475-1489.
19. Ivarsson,Y., Mackey,A.J., Edalat,M., Pearson,W.R. and Mannervik,B. (2003). J. Biol. Chem., 278, 8733-8738.
20. Ji,X., Johnson,W.W., Sesay,M.A., Dickert,L., Prasad,S.M., Ammon,H.L., Armstrong,R.N. and Gilliland,G.L. (1994) Biochemistry, 33, 1043-1052.
21. Johansson,A.-S., Bolton-Grob,R. and Mannervik,B. (1999) Protein Expr. Purif., 17, 105-112.
22. Johansson,A.-S. and Mannervik,B. (2001) In Pacifici,G.M. and Pelkonen,O. (eds), Interindividual Variability in Human Drug Metabolism. Taylor and Francis, London, pp. 460-519.
23. Johnson,W.W., Liu,S., Ji,X., Gilliland,G.L. and Armstrong,R.N. (1993) J. Biol. Chem., 268, 11508-11511.
24. Mannervik,B. and Widersten,M. (1995) In Pacifici,G.M. and Fracchia,G.N. (eds), Advances in Drug Metabolism in Man. European Commission, Luxembourg, pp. 408-459.
25. Mannervik,B. et al. (1992) Biochem. J., 282, 305-306.
26. McCallum,S.A., Hitchens,T.K., Torborg,C. and Rule,G.S. (2000) Biochemistry, 39, 7343-7356.
27. McLellan,R.A., Oscarson,M., Alexandrie,A.K., Seidegård,J., Evans,D.A., Rannug,A. and Ingelman-Sundberg,M. (1997) Mol. Pharmacol., 52, 958-965.
28. Morisseau,C. and Hammock,B.D. (2005) Annu. Rev. Pharmacol. Toxicol., 45, 311-333.
29. Pacifici,G.M., Warholm,M., Guthenberg,C., Mannervik,B. and Rane,A. (1987) Hum. Toxicol., 6, 483-489.
30. Patskovsky,Y.V., Patskovska,L.N. and Listowsky,I. (2000) J. Biol. Chem., 275, 3296-3304.
31. Raghunathan,S., Chandross,R.J., Kretsinger,R.H., Allison,T.J., Penington,C.J. and Rule,G.S. (1994) J. Mol. Biol., 238, 815-832.
32. Rannug,U., Sundvall,A. and Ramel,C. (1978) Chem.-Biol. Interact., 20, 1-16.
33. Ridder,L., Rietjens,I.M., Vervoort,J. and Mulholland,A.J. (2002) J. Am. Chem. Soc., 124, 9926-9936.
34. Seidegård,J., Vorachek,W.R., Pero,R.W. and Pearson,W.R. (1988) Proc. Natl Acad. Sci. USA, 85, 7293-7297.
35. Shan,S. and Armstrong,R.N. (1994) J. Biol. Chem., 269, 32373-32379.
36. Sheehan,D., Meade,G., Foley,V.M. and Dowd,C.A. (2001) Biochem. J., 360, 1-16.
37. Sundberg,K., Widersten,M., Seidel,A., Mannervik,B. and Jernström,B. (1997) Chem. Res. Toxicol., 10, 1221-1227.
38. Warholm,M., Guthenberg,C., Mannervik,B., von Bahr,C. and Glaumann,H. (1980) Acta Chem. Scand. B, 34, 607-621.
39. Warholm,M., Guthenberg,C., Mannervik,B. and von Bahr,C. (1981) Biochem. Biophys. Res. Commun., 98, 512-519.
40. Widersten,M., Huang,M. and Mannervik,B. (1996) Protein Expr. Purif., 7, 367-372.