Microbial transformations of styrene and [14C] styrene in soil and enrichment cultures

Sielicki, M.; Focht, D. D.; Martin, James P.

doi:10.1128/aem.35.1.124-128.1978

Cited by 40 publications

(12 citation statements)

References 19 publications

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“…These compounds have both been proposed as initial transformation products in the aerobic degradation of styrene (Fig. 2) (11,13). Although both styrene oxide and 2-phenylethanol were oxidized by styrenegrown cells (Table 1) Reactions: 1, oxidation of styrene to styrene oxide by a Pseudomonas sp.…”

Section: Downloaded Frommentioning

confidence: 98%

Metabolism of Styrene Oxide and 2-Phenylethanol in the Styrene-Degrading Xanthobacter Strain 124X

Hartmans¹,

Smits²,

Werf³

et al. 1989

Appl Environ Microbiol

354

190

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Styrene oxide and 2-phenylethanol metabolism in the styrene-degrading Xanthobacter sp. strain 124X was shown to proceed via phenylacetaldehyde and phenylacetic acid. In cell extracts 2-phenylethanol was oxidized by a phenazine methosulfate-dependent enzyme, probably a pyrroloquinoline quinone enzyme. Xanthobacter sp. strain 124X also contains a novel enzymatic activity designated as styrene oxide isomerase. Styrene oxide isomerase catalyzes the isomerization of styrene oxide to phenylacetaldehyde. The enzyme was partially purified and shown to have a very high substrate specificity. Of the epoxides tested, styrene oxide was the only substrate transformed. The initial step in styrene metabolism in Xanthobacter sp. strain 124X is oxygen dependent and probably involves oxidation of the aromatic nucleus.

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Section: Downloaded Frommentioning

confidence: 98%

Metabolism of Styrene Oxide and 2-Phenylethanol in the Styrene-Degrading Xanthobacter Strain 124X

Hartmans¹,

Smits²,

Werf³

et al. 1989

Appl Environ Microbiol

354

190

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“…Alternative routes for aerobic microbial degradation of styrene have been described earlier. Degradation of styrene by enrichment cultures was shown to yield 2-phenylethanol and phenylacetate [1]. 2-Phenylethanol was produced from styrene by pure bacterial cultures as well [21.…”

Section: Introductionmentioning

confidence: 99%

Degradation of styrene and ethylbenzene by Pseudomonas species Y2

Utkin

1991

FEMS Microbiology Letters

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Summary Pseudomonas species Y2 is able to grow on styrene, ethylbenzene, 2‐phenylethanol, 1‐phenylethanol, acetophenone, phenylacetate, and mandelate as a sole source of carbon and energy. Ethylbenzene is transformed by Y2 cells to yield 1‐phenylethanol, 2‐phenylethanol, phenylacetate, and four novel products: acetophenone, salicylate, 2‐hydroxyphenylacetate, and mandelate. Salicylate, 2‐hydroxyphenylacetate, 1‐ and 2‐phenylethanol are produced from styrene. The formation of 1‐phenylethanol and salicylate from styrene has not been previously described. Our growth experiments have shown that styrene and ethylbenzene are catabolized via 2‐phenylethanol and phenylacetate. It is the first report of the ethylbenzene pathway. Ethylbenzene is also catabolized via 1‐phenylethanol. The induction of catechol 2,3‐dioxygenase by growing the organism on ethylbenzene and 1‐pheny lethanol indicates that these compounds could be degraded via the corresponding catechols and then via extradiol cleavage of the aromatic ring.

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“…Initial attempts to isolate organisms that could grow on styrene were unsuccessful, probably because the concentrations of styrene used for the isolation were too high, for example 0.1 mol styrene 1-' used by Sielicki et al (1978a).…”

Section: I C R O B I a L M E T A B O L I S M Of Styrenementioning

confidence: 99%

“…The majority of organisms investigated have been found to use a pathway which converts styrene to 2-phenylethanol or phenylacetic acid. Sielicki et al (1978a) isolated a mixed culture which could degrade styrene, and found that phenylacetic acid and 2-phenylethanol were present in the growth medium. Shirai and Hisatsuka (1979a) isolated…”

Section: Breakdown Via Phenylacetic Acidmentioning

confidence: 99%

Microbial metabolism and biotransformations of styrene

Warhurst

Fewson

1994

Journal of Applied Bacteriology

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1. Introduction, 597 2. Metabolism of styrene in the liver, 598 3. Microbial metabolism of styrene 3.1 Ring attack, 599 3.2 Metabolism through phenylethanediol, 600 3.3 Breakdown via phenylacetic acid, 600 3.4 Breakdown via I-phenylethanol, 601 3.5 Anaerobic breakdown, 602 4. Microbial metabolism of styrene oligomers, 602 -Styrene is an important industrial chemical and it is also produced naturally, mainly by the decarboxylation of cinnamic acid. I t possesses both an aromatic ring and a vinyl side-chain and so there are many possible routes for its metabolism. Mammalian liver oxidizes styrene, attacking its side-chain to give styrene oxide, followed by hydration to yield phenylethanediol. A strain of Pseudomonas putida has been reported to use the same route. Initial dioxygenase ring attack followed by meta-cleavage of the ring occurs in a strain of Rhodococcus rhodochrous, and it has been suggested that initial ring attack occurs in other organisms. Many isolates degrade styrene through phenylacetic acid, and in one of these bacteria certain of the enzymes have been shown to be plasmid-encoded. Styrene can be degraded anaerobically by both consortia and pure cultures. Bacteria are able to metabolize u-and 0-styrene as well as styrene dimers and tetramers, although higher oligomers of styrene are recalcitrant. Styrene-degrading organisms have been used in experimental gas filters, and chiral synthetic precursors based on styrene can be produced using microbial enzymes.

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Microbial transformations of styrene and [14C] styrene in soil and enrichment cultures

Cited by 40 publications

References 19 publications

Metabolism of Styrene Oxide and 2-Phenylethanol in the Styrene-Degrading Xanthobacter Strain 124X

Metabolism of Styrene Oxide and 2-Phenylethanol in the Styrene-Degrading Xanthobacter Strain 124X

Degradation of styrene and ethylbenzene by Pseudomonas species Y2

Microbial metabolism and biotransformations of styrene

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