Chiral inversion of 2-arylpropionoic acid (2-APA) enantiomers during simulated biological wastewater treatment

Nguyen, Anh Q.; Nguyen, Luong N.; McDonald, James A.; Leusch, Frederic; Neale, Peta A.; Khan, Stuart J.

doi:10.1016/j.watres.2021.117871

Cited by 6 publications

(5 citation statements)

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“…Chiral inversion behavior observed under anaerobic and aerobic conditions was similar for six compounds: 2-(3-chlorophenyl)propionic acid, 2-(3-methylphenyl)propionic acid, 2-(4-fluorophenyl)propionic acid, 2-(4-butylphenyl)propionic acid, 2-(4- tert -butylphenyl)propionic acid, and flurbiprofen (Table S7). Meanwhile, the remaining five compounds showed different chiral inversion behaviors under aerobic and anaerobic conditions. , In addition, chiral inversion under anaerobic conditions happened at a limited extent compared to that under aerobic conditions. These differences in chiral inversion behavior could be due to the difference between aerobic and anaerobic microbial communities.…”

Section: Results and Discussionmentioning

confidence: 95%

“…Duplicate samples of the feed (50 mL each) were prepared in the same protocol, filtered, diluted 10 times with Milli-Q water into 500 mL, and mixed with 50 μL of the ISTD. Solid phase extraction, diastereomer preparation, and enantio-specific analysis of chiral 2-APAs using GC–MS/MS were performed following a previously described analytical method …”

Section: Methodsmentioning

confidence: 99%

“…Solid phase extraction, diastereomer preparation, and enantio-specific analysis of chiral 2-APAs using GC−MS/MS were performed following a previously described analytical method. 18 2.3.4. Removal Efficiency and Enantiomeric Fraction.…”

Section: Methodsmentioning

confidence: 99%

“…Meanwhile, the remaining five compounds showed different chiral inversion behaviors under aerobic and anaerobic conditions. 18,19 In addition, chiral inversion under anaerobic conditions happened at a limited extent compared to that under aerobic conditions. These differences in chiral inversion behavior could be due to the difference between aerobic and anaerobic microbial communities.…”

Section: Chiral Inversion Under Anaerobic Conditionsmentioning

confidence: 99%

“…Based on the enantio-specific analyses of effluents from municipal wastewater treatment plants (WWTPs) and untreated sewage, chiral inversion of NSAIDs can be expected during wastewater treatment . Indeed, recent studies of NSAIDs and other 2-APA derivatives in controlled reactors have confirmed the occurrence of chiral inversion in aerobic wastewater treatment processes. − In a previous study, using pure enantiomers, Nguyen et al reported diverse chiral inversion behaviors of 11 2-APAs during membrane bioreactor (MBR) treatment. They observed unidirectional inversion in the ( R → S ) and ( S → R ) directions as well as bidirectional chiral inversion of these 2-APAs under aerobic conditions.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Inversion of 2-Arylpropionic Acid Enantiomers under Anaerobic Conditions

Nguyễn

McDonald

et al. 2022

Environ. Sci. Technol.

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This work examined the chiral inversion of 2-arylpropionic acids (2-APAs) under anaerobic conditions and the associated microbial community. The anaerobic condition was simulated by two identical anaerobic digesters. Each digester was fed with the substrate containing 11 either pure (R)- or pure (S)-2-APA enantiomers. Chiral inversion was evidenced by the concentration increase of the other enantiomer in the digestate and the changes in the enantiomeric fraction between the two enantiomers. Both digesters showed similar and poor removal of 2-APAs (≤30%, except for naproxen) and diverse chiral inversion behaviors under anaerobic conditions. Four compounds exhibited (S → R) unidirectional inversion [flurbiprofen, ketoprofen, naproxen, and 2-(4-tert-butylphenyl)propionic acid], and the remaining seven compounds showed bidirectional inversion. Several aerobic and facultative anaerobic bacterial genera (Candidatus Microthrix, Rhodococcus, Mycobacterium, Gordonia, and Sphingobium) were identified in both digesters and predicted to harbor the 2-arylpropionyl-CoA epimerase (enzyme involved in chiral inversion) encoding gene. These genera presented at low abundances, <0.5% in the digester dosed with (R)-2-APAs and <0.2% in the digester dosed with (S)-2-APAs. The low abundances of these genera explain the limited extent of chiral inversion observed in this study.

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Section: Results and Discussionmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chiral Inversion Under Anaerobic Conditionsmentioning

confidence: 99%