Enantioselective Metabolism of Chiral 3-Phenylbutyric Acid, an Intermediate of Linear Alkylbenzene Degradation, by Rhodococcus rhodochrous PB1

Simoni, S.; Klinke, Stefan; Zipper, Christian; Angst, Werner; Köhler, Hans Peter

doi:10.1128/aem.62.3.749-755.1996

“…Only the (R) enantiomer supports growth of strain PB1. The (S) enantiomer is transformed to a reactive intermediate that accumulates in the culture medium (Simoni et al 1996). Ludwig et al (Ludwig et al 1992) showed that only (R)-dichlorprop is degraded by a mixed culture of marine microorganisms under aerobic laboratory conditions, a finding that is in agreement with analyses of North Sea water samples, in which an enrichment of (S)-dichlorprop was found.…”

Section: Introductionsupporting

confidence: 69%

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Zipper

¹

,

Bolliger

²

,

Fleischmann

³

et al. 1999

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Aerobic degradation experiments with the racemic mixtures of mecoprop and dichlorprop revealed that activated sludge collected from the aeration tank of a municipal waste water treatment plant degraded both enantiomers of mecoprop and dichlorprop within 7 days, albeit in an enantioselective manner; the (S) enantiomers were preferentially degraded. Mecoprop, dichlorprop, and 2,4-D were completely metabolized under aerobic conditions, as shown by the 86-98% elimination of dissolved organic carbon. Under anaerobic conditions, the concentration of 2,4-D decreased exponentially with a first-order reaction rate constant of 0.24 per day and without a lag-phase. After an incubation time of 17 days, 2,4-D was completely removed. 2,4-Dichlorophenol was the main metabolite of anaerobic 2,4-D degradation; only traces of 4-chlorophenol were detected. In contrast, the chiral phenoxypropionic acid herbicides mecoprop and dichlorprop persisted under anaerobic conditions during 49 days of incubation.

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“…(i) Many chiral pollutants are released into the environment as racemic mixtures [8,9]. (ii) One enantiomer of a racemic mixture may be rapidly and completely degraded, while the other enantiomer may be resistant to microbial attack [10,11]. This can lead to an accumulation of the more recalcitrant enantiomer in the environment [10,12].…”

Section: Introductionmentioning

confidence: 99%

Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge

Zipper

¹

,

Fleischmann

²

,

Kohler

³

1999

FEMS Microbiology Ecology

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The aerobic biodegradation of racemic mixtures of five chiral phenoxyalkanoic acids was studied according to a biodegradation test that was complemented with enantiomer‐specific analysis. Both enantiomers of (RS)‐2‐phenoxypropanoic acid, (RS)‐2‐(3‐chlorophenoxy)propanoic acid, and (RS)‐2‐(4‐chlorophenoxy)propanoic acid, were completely degraded within 25 days when aerobically incubated with activated sludge. During incubations of (RS)‐2‐phenoxypropanoic acid, the (R) enantiomer was degraded before the (S) enantiomer, whereas during incubations of (RS)‐2‐(3‐chlorophenoxy)propanoic acid the (S) enantiomer was preferentially degraded. The (R) enantiomer of (RS)‐2‐(2‐chlorophenoxy)propanoic acid was removed after 24 days while only 30% of the (S) enantiomer was degraded within 47 days of incubation. (RS)‐2‐(2,4,5‐Trichlorophenoxy)propanoic acid was the most persistent of all the racemic mixtures tested. After 47 days, the concentration of the (S) enantiomer was nearly unchanged, and the concentration of (R)‐2‐(2,4,5‐trichlorophenoxy)propanoic acid had decreased only by about 40%. The differences observed in the length of the lag phases and in the degradation rates of individual enantiomers can lead to accumulations of the more recalcitrant enantiomer in aquatic or terrestrial ecosystems.

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“…(i) Many chiral pollutants are released into the environment as racemic mixtures [8,9]. (ii) One enantiomer of a racemic mixture may be rapidly and completely degraded, while the other enantiomer may be resistant to microbial attack [10,11]. This can lead to an accumulation of the more recalcitrant enantiomer in the environment [10,12].…”

Section: Introductionmentioning

confidence: 99%

Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge

Zipper¹

1999

FEMS Microbiology Ecology

Self Cite

3

2

0

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The aerobic biodegradation of racemic mixtures of five chiral phenoxyalkanoic acids was studied according to a biodegradation test that was complemented with enantiomer‐specific analysis. Both enantiomers of (RS)‐2‐phenoxypropanoic acid, (RS)‐2‐(3‐chlorophenoxy)propanoic acid, and (RS)‐2‐(4‐chlorophenoxy)propanoic acid, were completely degraded within 25 days when aerobically incubated with activated sludge. During incubations of (RS)‐2‐phenoxypropanoic acid, the (R) enantiomer was degraded before the (S) enantiomer, whereas during incubations of (RS)‐2‐(3‐chlorophenoxy)propanoic acid the (S) enantiomer was preferentially degraded. The (R) enantiomer of (RS)‐2‐(2‐chlorophenoxy)propanoic acid was removed after 24 days while only 30% of the (S) enantiomer was degraded within 47 days of incubation. (RS)‐2‐(2,4,5‐Trichlorophenoxy)propanoic acid was the most persistent of all the racemic mixtures tested. After 47 days, the concentration of the (S) enantiomer was nearly unchanged, and the concentration of (R)‐2‐(2,4,5‐trichlorophenoxy)propanoic acid had decreased only by about 40%. The differences observed in the length of the lag phases and in the degradation rates of individual enantiomers can lead to accumulations of the more recalcitrant enantiomer in aquatic or terrestrial ecosystems.

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Enantioselective Metabolism of Chiral 3-Phenylbutyric Acid, an Intermediate of Linear Alkylbenzene Degradation, by Rhodococcus rhodochrous PB1

Cited by 25 publications

References 33 publications

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Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge

Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge

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