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Applied and Environmental Microbiology, May 2000, p. 1877-1882, Vol. 66, No. 5
Envirogen, Inc., Lawrenceville, New Jersey
08648,1 and Department of Biochemistry,
College of Agricultural and Life Sciences, University of Wisconsin,
Madison, Wisconsin 537052
Received 30 August 1999/Accepted 20 February 2000
Several toluene monooxygenase-producing organisms were tested for
their ability to oxidize linear alkenes and chloroalkenes three to
eight carbons long. Each of the wild-type organisms degraded all of the
alkenes that were tested. Epoxides were produced during the oxidation
of butene, butadiene, and pentene but not hexene or octadiene. A strain
of Escherichia coli expressing the cloned toluene-4-monooxygenase (T4MO) of Pseudomonas mendocina KR1
was able to oxidize butene, butadiene, pentene, and hexene but not octadiene, producing epoxides from all of the substrates that were
oxidized. A T4MO-deficient variant of P. mendocina KR1
oxidized alkenes that were five to eight carbons long, but no epoxides were detected, suggesting the presence of multiple alkene-degrading enzymes in this organism. The alkene oxidation rates varied widely (ranging from 0.01 to 0.33 µmol of substrate/min/mg of cell protein) and were specific for each organism-substrate pair. The enantiomeric purity of the epoxide products also varied widely, ranging from 54 to
>90% of a single epoxide enantiomer. In the absence of more preferred
substrates, such as toluene or alkenes, the epoxides underwent further
toluene monooxygenase-catalyzed transformations, forming products that
were not identified.
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Toluene Monooxygenase-Catalyzed Epoxidation
of Alkenes
*
Corresponding author. Mailing address: 4100 Quakerbridge Rd., Lawrenceville, NJ 08648. Phone: (609) 936-9300. Fax:
(609) 936-9221. E-mail: Steffan{at}envirogen.com.
Applied and Environmental Microbiology, May 2000, p. 1877-1882, Vol. 66, No. 5
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.
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