Facile determination of the absolute stereochemistry of hydroxy fatty acids by GC: application to the analysis of fatty acid oxidation by a P450BM3 mutant

Tetrahedron Asymmetry

Volumn 18, Issue 4, 2007, Pages 547-551

  Cryle, Max J ^a   De Voss, James J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; CYTOCHROME P450 BM3; HYDROXY FATTY ACID; IBUPROFEN; LAURIC ACID; PALMITIC ACID; THREONINE;

ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ELUTION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; FATTY ACID OXIDATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 33947276113     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.01.034     Document Type: Article

References (25)

1. Boddupalli S.S., Pramanik B.C., Slaughter C.A., Estabrook R.W., and Peterson J.A. Arch. Biochem. Biophys. 292 (1992) 20-28
2. Coon M.J., Vaz A.D.N., McGinnity D.F., and Peng H.-M. Drug Metab. Disp. 26 (1998) 1190-1193
3. Cryle M.J., and De Voss J.J. Chem. Commun. (2004) 86-87
4. Cryle M.J., and De Voss J.J. Angew. Chem., Int. Ed. 45 (2006) 8221-8223
5. Cryle M.J., Espinoza R.D., Smith S.J., Matovic N.J., and De Voss J.J. Chem. Commun. (2006) 2353-2355
6. Cryle M.J., Matovic N.J., and De Voss J.J. Org. Lett. 5 (2003) 3341-3344
7. Cryle M.J., Matovic N.J., and De Voss J.J. Tetrahedron Lett. 48 (2007) 133-136
8. Cryle M.J., Ortiz de Montellano P.R., and De Voss J.J. J. Org. Chem. 70 (2005) 2455-2469
9. Cryle M.J., Stok J.E., and De Voss J.J. Aus. J. Chem. 56 (2003) 749-762
10. Cryle M.J., Stuthe J.M.U., Ortiz de Montellano P.R., and De Voss J.J. Chem. Commun. (2004) 512-513
11. Imai M., Shimada H., Watanabe Y., Matsushima-Hibiya Y., Makino R., Koga H., Horiuchi T., and Ishimura Y. Proc. Natl. Acad. Sci. U.S.A. 86 (1989) 7823-7827
12. Jin S., Bryson T.A., and Dawson J.H. J. Biol. Inorg. Chem. 9 (2004) 644-653
13. Jin S., Makris T.M., Bryson T.A., Sligar S.G., and Dawson J.H. J. Am. Chem. Soc. 125 (2003) 3406-3407
14. Martinis S.A., Atkins W.M., Stayton P.S., and Sligar S.G. J. Am. Chem. Soc. 111 (1989) 9252-9253
15. Matovic, N. J. Honours Thesis, University of Queensland, 2002.
16. Mueller E.J., Loida P.L., and Sligar S.G. Twenty-Five Years of P450cam Research: Mechanistic Insights into Oxygenase Catalysis. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. 2nd ed. (1995), Plenum Press, New York 99
17. Munro A.W., Daff S., Coggins J.R., Lindsay J.G., and Chapman S.K. Eur. J. Biochem. 239 (1996) 403-409
18. Ortiz de Montellano P.R., and De Voss J.J. Nat. Prod. Rep. 19 (2002) 477-493
19. Ortiz de Montellano P.R., and De Voss J.J. Cytochrome P450: Structure, Mechanism, and Biochemistry, Third Edition. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. 3rd ed. (2005), Kluwer Academic/Plenum, New York 183
20. Poulos T.L., Cupp-Vickery J., and Li H. Structural Studies on Prokaryotic Cytochromes P450. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. 2nd ed. (1995), Plenum Press, New York 137
21. Truan G., Komandla M.R., Falck J.R., and Peterson J.A. Arch. Biochem. Biophys. 366 (1999) 192-198
22. Truan G., and Peterson J.A. Arch. Biochem. Biophys. 349 (1998) 53-64
23. Vaz A.D.N., McGinnity D.F., and Coon M.J. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 3555-3560
24. Vaz A.D.N., Pernecky S.J., Raner G.M., and Coon M.J. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 4644-4648
25. Yeom H., Sligar S.G., Li H., Poulos T.L., and Fulco A.J. Biochemistry 34 (1995) 14733-14740