Enzymatic oxidation of cyclopropylbenzene: structures of new metabolites and possible mechanistic implications

Canadian Science Publishing - Tập 80 Số 6 - Trang 708-713 - 2002
Vu Bui, Minh Thu Dinh Nguyen, Jeff Hansen, John M. Baker, Tomáš Hudlický

Tóm tắt

Cyclopropylbenzene was subjected to whole-cell fermentation with either Escherichia coli JM109 (pDTG601) or E. coli JM109 (pDTG602), expressing toluene dioxygenase and toluene dioxygenase – dihydrodiol dehydrogenase enzymes, respectively. The corresponding metabolites, 3-cyclopropylcyclohexa-3,5-diene-1,2-diol (3) and 3-cyclopropylbenzene-1,2-diol (5) have been isolated in yields of 2.5 and 1 g L–1, respectively. The absolute stereochemistry correlation for 3 is provided, along with a preliminary discussion of its potential in asymmetric synthesis. Possible mechanistic implications are indicated for the enzymatic oxygenation through the use of calculations. Experimental data are provided for all new compounds.Key words: cyclopropylbenzene, bio-oxidation, cis-diene diol, catechol, JM109 (pDTG601), JM109 (pDTG602), dioxygenase.

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Tài liệu tham khảo

Gibson J.R., 1968, Kallio. Biochemistry, 7, 3795, 10.1021/bi00851a003

Gibson M., 1970, J. Mabry. Biochemistry, 9, 1626, 10.1021/bi00809a023

Zylstra D.T., 1989, Gibson. J. Biol. Chem., 264, 14940, 10.1016/S0021-9258(18)63793-7

Simon T.D., 1993, J. Zylstra. Gene, 127, 31, 10.1016/0378-1119(93)90613-8

1989, J. Mondello. J. Bacteriol., 171, 1725, 10.1128/JB.171.3.1725-1732.1989

Kauppi K., 1998, Ramaswamy. Structure, 6, 571, 10.1016/S0969-2126(98)00059-8

Hudlicky D., 1999, Gibson. Aldrich. Acta, 32, 35

Ley F., 1987, Taylor. Tetrahedron Lett., 28, 225, 10.1016/S0040-4039(00)95692-2

Bui T.V, 2000, Hudlicky. Green Chem., 2, 263, 10.1039/b006988o

Johnston V., 1987, Renganathan. Enzyme Microb. Technol., 9, 706, 10.1016/0141-0229(87)90028-7

Bui T.V., 2001, Ribbons. New J. Chem., 25, 116, 10.1039/b006545p

Boyd M.R., Sheldrake. J. Chem. Soc. Chem. Commun., 1630

Yamamura I., 1975, Murahashi. J. Organomet. Chem., 91, C39, 10.1016/S0022-328X(00)89636-9

Wender H., 1995, Witulski. J. Am. Chem. Soc., 117, 4720, 10.1021/ja00121a036

Dinnocenzo D.A., 1988, Conlon. J. Am. Chem. Soc., 110, 2324, 10.1021/ja00215a066

Gibson E., 2000, Ramaswamy. J. Mol. Biol., 296, 701, 10.1006/jmbi.1999.3462

Baldwin R.M., 1987, Ting. J. Chem. Soc. Chem. Commun., 1661

Birladeanu T., 1966, Winstein. J. Am. Chem. Soc., 88, 2316, 10.1021/ja00962a042

1993, Becke. J. Chem. Phys., 98, 5648, 10.1063/1.464913

Smith A., 1998, Radom. J. Am. Chem. Soc., 120, 10223, 10.1021/ja980635m

Hariharan J.A., 1973, Pople. Theor. Chem. Acta, 28, 213, 10.1007/BF00533485

Raghavachari G.W., 1989, Trucks. J. Chem. Phys., 91, 1062, 10.1063/1.457230

Newcomb A.G., 1989, Glenn. J. Am. Chem. Soc., 111, 275, 10.1021/ja00183a041

Beckwith V.W., 1994, Bowry. J. Am. Chem. Soc., 116, 2710, 10.1021/ja00086a003

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Canadian Science Publishing

Tập 80 Số 6

708-713

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