Enzymatic oxidation of cyclopropyl benzene: structures of new metabolites and possible mechanistic implications

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-die...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 80; no. 6; pp. 708 - 713
Main Authors Bui, VP, Nguyen, M, Hansen, J, Baker, J, Hudlicky, T
Format Journal Article
LanguageEnglish
Published OTTAWA Canadian Science Publishing 01.06.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
JM109 (pDTG602)
DESIGN
RADICAL-ION PROBES
ESCHERICHIA-COLI
dioxygenase
VINYLCYCLOPROPANES
cyclopropylbenzene
REARRANGEMENTS
JM109 (pDTG601)
catechol
DIHYDROXYLATION
CATECHOLS
GENES
TOLUENE DIOXYGENASE
CATALYZED 5+2 CYCLOADDITIONS
bio-oxidation
cis-diene diol
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Summary: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.
ISSN:0008-4042
1480-3291
DOI:10.1139/V02-098