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Enantiomeric Fraction Determination of 2‐Arylpropionic Acids in a Package Plant Membrane Bioreactor
Author(s) -
Hashim Nor H.,
Stuetz Richard M.,
Khan Stuart J.
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22151
Subject(s) - chemistry , chromatography , enantiomer , effluent , naproxen , ketoprofen , diastereomer , membrane bioreactor , ibuprofen , bioreactor , organic chemistry , medicine , alternative medicine , pathology , environmental engineering , engineering , pharmacology
Enantiomeric compositions of three 2‐arylpropionic acid (2‐APA) drugs, ibuprofen, naproxen, and ketoprofen, were monitored in a membrane bioreactor (MBR) treating municipal effluent in a small rural town in Australia. Specific enantiomers were determined as amide diastereomers using the chiral derivatizing reagent, ( R )‐1‐phenylethylamine (PEA), followed by gas chromatography–tandem mass spectrometry (GC‐MS/MS). The six individual enantiomers were quantified by isotope dilution and the enantiomeric fractions (EFs) were determined. Over four separate sampling events, ibuprofen EF ranged from 0.88 to 0.94 (median 0.93) in the influent and 0.38 to 0.40 (median 0.39) in the effluent. However, no significant change in ketoprofen EF was observed, with influent EFs of 0.56–0.60 (median 0.58) and effluent EFs 0.54–0.68 (median 0.56). This is the first report of enantiospecific analysis of ketoprofen in municipal wastewater and it is not yet clear why such different behavior was observed compared to ibuprofen. Naproxen EF was consistently measured at 0.99 in the influent and ranged from 0.86 to 0.94 (median 0.91) in the effluent. This study demonstrates that EF is a relatively stable parameter and does not fluctuate according to concentration or other short‐term variables introduced by sampling limitations. The enantiospecific analysis of chiral chemicals presents a promising approach to elucidate a more thorough understanding of biological treatment processes and a potential tool for monitoring the performance of key biological pathways. Chirality 25:301–307, 2013 . © 2013 Wiley Periodicals, Inc.