The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

Tetrahedron Letters

Volumn 48, Issue 1, 2007, Pages 133-136

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

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

BM3; CYP102A1; Cytochrome P450; Oxidation mechanism; Regiochemistry; Stereochemistry

Indexed keywords

ALCOHOL; CYTOCHROME P450; DECANOIC ACID DERIVATIVE; FATTY ACID; MYRISTIC ACID DERIVATIVE; PALMITIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; ENANTIOSELECTIVITY; FATTY ACID SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33751396914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.136     Document Type: Article

References (19)

1. Cryle M.J., Stok J.E., and De Voss J.J. Aust. J. Chem. 56 (2003) 749-762
2. Ortiz de Montellano P.R., and De Voss J.J. Nat. Prod. Rep. 19 (2002) 477-493
3. Cryle M.J., Matovic N.J., and De Voss J.J. Org. Lett. 5 (2003) 3341-3344
4. Cryle M.J., and De Voss J.J. Chem. Commun. (2004) 86-87
5. Cryle M.J., Espinoza R.D., Smith S.J., Matovic N.J., and De Voss J.J. Chem. Commun. (2006) 2353-2355
6. He X., Cryle M.J., De Voss J.J., and Ortiz de Montellano P.R. J. Biol. Chem. 280 (2005) 22697-22705
7. Cryle M.J., Ortiz de Montellano P.R., and De Voss J.J. J. Org. Chem. 70 (2005) 2455-2469
8. Cryle M.J., Stuthe J.M.U., Ortiz de Montellano P.R., and De Voss J.J. Chem. Commun. (2004) 512-513
9. Cryle, M. J.; De Voss, J. J. Angew. Chem., Int. Ed., in press, doi:10.1002/anie.200603411.
10. Boddupalli S.S., Pramanik B.C., Slaughter C.A., Estabrook R.W., and Peterson J.A. Arch. Biochem. Biophys. 292 (1992) 8-20
11. Truan G., Komandla M.R., Falck J.R., and Peterson J.A. Arch. Biochem. Biophys. 366 (1999) 192-198
12. Capdevila J.H., Wei S., Helvig C., Falck J.R., Belosludtsev Y., Truan G., Graham-Lorence S.E., and Peterson J.A. J. Biol. Chem. 271 (1996) 22663-22671
13. Schneider S., Wubbolts M.G., Sanglard D., and Witholt B. Tetrahedron: Asymmetry 9 (1998) 2833-2844
14. Morr M., Proppe C., and Wray V. Liebigs. Ann. (1995) 2001-2004
15. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986-2012
16. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. 95 (1973) 512-519
17. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543-2549
18. Voss G., and Gerlach H. Helv. Chim. Acta 66 (1983) 2294-2307
19. Matovic, N. J. Unpublished results, 2003.