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Article: Enantioselective degradation and unidirectional chiral inversion of 2-phenylbutyric acid, an intermediate from linear alkylbenzene, by Xanthobacter flavus PA1

TitleEnantioselective degradation and unidirectional chiral inversion of 2-phenylbutyric acid, an intermediate from linear alkylbenzene, by Xanthobacter flavus PA1
Authors
Keywords2-Phenylbutyric acid
Chiral inversion
Enantioselective biodegradation
Linear alkylbenzene sulfonates
Xanthobacter flavus
Issue Date2011
PublisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/jhazmat
Citation
Journal Of Hazardous Materials, 2011, v. 192 n. 3, p. 1633-1640 How to Cite?
AbstractMicrobial degradation of the chiral 2-phenylbutyric acid (2-PBA), a metabolite of surfactant linear alkylbenzene sulfonates (LAS), was investigated using both racemic and enantiomer-pure compounds together with quantitative stereoselective analyses. A pure culture of bacteria, identified as Xanthobacter flavus strain PA1 isolated from the mangrove sediment of Hong Kong Mai Po Nature Reserve, was able to utilize the racemic 2-PBA as well as the single enantiomers as the sole source of carbon and energy. In the presence of the racemic compounds, X. flavus PA1 degraded both (R) and (S) forms of enantiomers to completion in a sequential manner in which the (S) enantiomer disappeared much faster than the (R) enantiomer. When the single pure enantiomer was supplied as the sole substrate, a unidirectional chiral inversion involving (S) enantiomer to (R) enantiomer was evident. No major difference was observed in the degradation intermediates with either of the individual enantiomers when used as the growth substrate. Two major degradation intermediates were detected and identified as 3-hydroxy-2-phenylbutanoic acid and 4-methyl-3-phenyloxetan-2-one, using a combination of liquid chromatography-mass spectrometry (LC-MS), and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The biochemical degradation pathway follows an initial oxidation of the alkyl side chain before aromatic ring cleavage. This study reveals new evidence for enantiomeric inversion catalyzed by pure culture of environmental bacteria and emphasizes the significant differences between the two enantiomers in their environmental fates. © 2011 Elsevier B.V.
Persistent Identifierhttp://hdl.handle.net/10722/139075
ISSN
2015 Impact Factor: 4.836
2015 SCImago Journal Rankings: 1.692
ISI Accession Number ID
Funding AgencyGrant Number
Faculty of Science, Faculty of Engineering
University of Hong Kong on Sustainable Water
Funding Information:

This research project was supported in part by grants from Faculty of Science, Faculty of Engineering and The University of Hong Kong on Sustainable Water. We would like to thank Xiang Li and Baofu Zheng for their help with NMR spectrometry and stimulating discussions on enantiomer-specific analyses, Li Pan for 16S rRNA gene sequencing, and Jessie Lai for laboratory assistance.

References

 

DC FieldValueLanguage
dc.contributor.authorLiu, Yen_HK
dc.contributor.authorHan, Pen_HK
dc.contributor.authorLi, XYen_HK
dc.contributor.authorShih, Ken_HK
dc.contributor.authorGu, JDen_HK
dc.date.accessioned2011-09-23T05:44:48Z-
dc.date.available2011-09-23T05:44:48Z-
dc.date.issued2011en_HK
dc.identifier.citationJournal Of Hazardous Materials, 2011, v. 192 n. 3, p. 1633-1640en_HK
dc.identifier.issn0304-3894en_HK
dc.identifier.urihttp://hdl.handle.net/10722/139075-
dc.description.abstractMicrobial degradation of the chiral 2-phenylbutyric acid (2-PBA), a metabolite of surfactant linear alkylbenzene sulfonates (LAS), was investigated using both racemic and enantiomer-pure compounds together with quantitative stereoselective analyses. A pure culture of bacteria, identified as Xanthobacter flavus strain PA1 isolated from the mangrove sediment of Hong Kong Mai Po Nature Reserve, was able to utilize the racemic 2-PBA as well as the single enantiomers as the sole source of carbon and energy. In the presence of the racemic compounds, X. flavus PA1 degraded both (R) and (S) forms of enantiomers to completion in a sequential manner in which the (S) enantiomer disappeared much faster than the (R) enantiomer. When the single pure enantiomer was supplied as the sole substrate, a unidirectional chiral inversion involving (S) enantiomer to (R) enantiomer was evident. No major difference was observed in the degradation intermediates with either of the individual enantiomers when used as the growth substrate. Two major degradation intermediates were detected and identified as 3-hydroxy-2-phenylbutanoic acid and 4-methyl-3-phenyloxetan-2-one, using a combination of liquid chromatography-mass spectrometry (LC-MS), and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The biochemical degradation pathway follows an initial oxidation of the alkyl side chain before aromatic ring cleavage. This study reveals new evidence for enantiomeric inversion catalyzed by pure culture of environmental bacteria and emphasizes the significant differences between the two enantiomers in their environmental fates. © 2011 Elsevier B.V.en_HK
dc.languageengen_US
dc.publisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/jhazmaten_HK
dc.relation.ispartofJournal of Hazardous Materialsen_HK
dc.subject2-Phenylbutyric aciden_HK
dc.subjectChiral inversionen_HK
dc.subjectEnantioselective biodegradationen_HK
dc.subjectLinear alkylbenzene sulfonatesen_HK
dc.subjectXanthobacter flavusen_HK
dc.titleEnantioselective degradation and unidirectional chiral inversion of 2-phenylbutyric acid, an intermediate from linear alkylbenzene, by Xanthobacter flavus PA1en_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0304-3894&volume=192&issue=3&spage=1633&epage=1640&date=2011&atitle=Enantioselective+degradation+and+unidirectional+chiral+inversion+of+2-phenylbutyric+acid,+an+intermediate+from+linear+alkylbenzene,+by+Xanthobacter+flavus+PA1-
dc.identifier.emailLi, XY: xlia@hkucc.hku.hken_HK
dc.identifier.emailShih, K: kshih@hkucc.hku.hken_HK
dc.identifier.emailGu, JD: jdgu@hkucc.hku.hken_HK
dc.identifier.authorityLi, XY=rp00222en_HK
dc.identifier.authorityShih, K=rp00167en_HK
dc.identifier.authorityGu, JD=rp00701en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.jhazmat.2011.06.088en_HK
dc.identifier.pmid21794984-
dc.identifier.scopuseid_2-s2.0-80052032514en_HK
dc.identifier.hkuros194852en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-80052032514&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume192en_HK
dc.identifier.issue3en_HK
dc.identifier.spage1633en_HK
dc.identifier.epage1640en_HK
dc.identifier.isiWOS:000295236800089-
dc.publisher.placeNetherlandsen_HK
dc.identifier.scopusauthoridLiu, Y=50561648000en_HK
dc.identifier.scopusauthoridHan, P=50561274000en_HK
dc.identifier.scopusauthoridLi, XY=26642887900en_HK
dc.identifier.scopusauthoridShih, K=14072108900en_HK
dc.identifier.scopusauthoridGu, JD=7403129601en_HK
dc.identifier.citeulike9528734-

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