Chiral Inversion of 2-Arylpropionic Acid Enantiomers under Anaerobic Conditions

Quynh Anh Nguyen; Hang P. Vu; James A McDonald

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Chiral Inversion of 2-Arylpropionic Acid Enantiomers under Anaerobic Conditions

机译：Chiral Inversion of 2-Arylpropionic Acid Enantiomers under Anaerobic Conditions

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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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《Environmental Science & Technology: ES&T》 |2022年第12期|8192-8208|共17页
作者
Quynh Anh Nguyen; Hang P. Vu; James A McDonald;
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作者单位

Centre for Technology in Water and Wastewater, School of Civil and Environmental Engineering, University of Technology Sydney, Ultimo 2007 New South Wales, Australia;

Centre for Technology in Water and Wastewater, School of Civil and Environmental Engineering University of Technology Sydney, Ultimo 2007 New South Wales, Australia;

Water Research Centre, School of Civil and Environmental Engineering University of New South Wales, Sydney 2052 New South Wales, Australia;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种英语
中图分类环境科学、安全科学;
关键词
non-steroidal anti-inflammatory drugs; chiral inversion; 2-arylpropionic acids; anaerobic waste treatment; microbial community; 2-arylpropionyl-CoA epimerase;

Chiral Inversion of 2-Arylpropionic Acid Enantiomers under Anaerobic Conditions

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