Naphthalene-dioxygenase-catalysed cis-dihydroxylation of azaarene derivatives. Part 1: 2-Pyridones and 2-quinolones

Journal of Molecular Catalysis B: Enzymatic

Volumn 50, Issue 2-4, 2008, Pages 53-60

  Chopard, Claude ^a   Azerad, Robert ^a   Prangé, Thierry ^b  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Dihydroxylation; N Methyl 2 pyridone; N Methyl 2 quinolone; Naphthalene dioxygenase; Pseudomonas sp.

Indexed keywords

AROMATIC COMPOUNDS; BACTERIA; HYDROXYLATION; STEREOCHEMISTRY;

DIHYDROXYLATION; N-METHYL-2-PYRIDONE; N-METHYL-2-QUINOLONE; NAPHTHALENE-DIOXYGENASE; PSEUDOMONAS SP.;

ENZYMES;

2 PYRIDONE DERIVATIVE; DIOXYGENASE; METHYL GROUP; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLONE DERIVATIVE;

ARTICLE; BACTERIAL CELL; BIOTRANSFORMATION; DEALKYLATION; DIHYDROXYLATION; ENZYME MECHANISM; ESCHERICHIA COLI; NONHUMAN; PSEUDOMONAS; STEREOCHEMISTRY;

PSEUDOMONAS SP.; PSEUDOMONAS SP. NCIB9816-4;

EID: 36849016356     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2007.09.013     Document Type: Article

References (28)

1. Boyd D.R., and Scheldrake G.N. Nat. Prod. Rep. (1998) 683-684
2. Hudlicky T., Gonzales D., and Gibson D.T. Aldrichim. Acta 32 (1999) 35-62
3. Johnson R.A. In: Overman L.E. (Ed). Organic Reactions 63 (2004), John Wiley & Sons 117-264
4. Endoma M.A., Bui V.P., Hansen J., and Hudlicky T. Org. Proc. Res. Dev. 6 (2002) 525-532
5. Boyd D.R., McMordie R.A.S., Porter H.P., Dalton H., Jenkins R.O., and Howarth O.W. Chem. Commun. (1987) 1722-1724
6. Boyd D.R., Sharma N.D., Brannigan I.N., Haughey S.A., Malone J.F., Clarke D.A., and Dalton H. Chem. Commun. (1996) 2361-2362
7. Boyd D.R., Sharma N.D., Caroll J.G., Allen C.C.R., Clarke D.A., and Gibson D.T. Chem. Commun. (1999) 1201-1202
8. Boyd D.R., Sharma N.D., Dorrity M.R.J., Hand M.V., McMordie R.A.S., Malone J.F., Porter H.P., Dalton H., Chima J., and Sheldrake G.N. J. Chem. Soc. Perkin Trans. 1 (1993) 1065-1071
9. Boyd D.R., Sharma N.D., Caroll J.G., Malone J.F., Mackerracher D.G., and Allen C.C.R. Chem. Commun. (1998) 549-559
10. Boyd D.R., Sharma N.D., Boyle R., McMurray B.T., Evans T.A., Malone J.F., Dalton H., Chima J., and Sheldrake G.N. Chem. Commun. (1993) 49-51
11. Boyd D.R., Sharma N.D., Boyle R., Malone J.F., Chima J., and Dalton H. Tetrahedron: Asymm. 4 (1993) 1307-1324
12. Boyd D.R., Sharma N.D., Modyanova L.V., Caroll J.G., Malone J.F., Allen C.C.R., Hamilton J.T.G., Gibson D.T., Parales R.E., and Dalton H. Can. J. Chem. 80 (2002) 589-600
13. Modyanova L., and Azerad R. Tetrahedron Lett. 41 (2000) 3865-3869
14. Hopkins G.C., Jonak J.P., Minnemeyer H., and Tieckelmann H. J. Org. Chem. 32 (1967) 4040-4044
15. Lee K., Resnick S.M., and Gibson D.T. Appl. Environ. Microbiol. 63 (1997) 2067-2070
16. Hudlicky T., Boros C.H., and Boros E.E. Synthesis (1992) 174-178
17. Copies of coordinates can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: +44 1223 336 033).
18. Flack H.D. Acta Crystallogr. A39 (1983) 876-881
19. Sheldrick G.M., and Schneider T.R. Meth. Enzymol. 277 (1997) 319-343
20. Pérez-Fuertes Y., Kelly A.M., Johnson A.L., Arimori S., Bull S.D., and James T.D. Org. Lett. 8 (2006) 609-612
21. During the completion of the present work, the same group reported the application of this methodology, using enantiopure (S)-α-methylbenzylamine, to the determination of the enantiomeric purity of various aliphatic or alicyclic chiral diols (A.M. Kelly, Y. Perez-Fuertes, S. Arimori, S.D. Bull, T.D. James, Org. Lett. 8 (2006) 1971-1974). Importantly, in their paper the authors point out the free rotation occurring around the aryl-boron bond on the NMR time scale, indicating no possible involvement of a newly created asymmetric boron center.
22. Boyd D.R., and Bugg T.D.H. Org. Biomol. Chem. 4 (2006) 181-192
23. Torok D.S., Resnick S.M., Brand J.M., Cruden D.L., and Gibson D.T. J. Bacteriol. 177 (1995) 5799-5805
24. Boyd D.R., Sharma N.D., Kerley N.A., McMordie R.A.S., Sheldrake G.N., Williams P., and Dalton H. J. Chem. Soc. Perkin Trans. 1 (1996) 67-74
25. Boyd D.R., Sharma N.D., Boyle R., Evans T.A., Malone J.F., McCombe K.M., Dalton H., and Chima J. J. Chem. Soc. Perkin Trans. 1 (1996) 1757-1765
26. Resnick S.M., Torok D.S., Lee K., Brand J.M., and Gibson D.T. Appl. Environ. Microbiol. 60 (1994) 3323-3328
27. Gibson D.T., Resnick S.M., Lee K., Brand J.M., Torok D.S., Wackett L.P., Shoken M.J., and Haigler B.E. J. Bacteriol. 177 (1995) 2615-2621
28. Resnick S.M., and Gibson D.T. Appl. Environ. Microbiol. 62 (1996) 3355-3359