Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum

Knobloch, Marco C.; Mathis, Flurin; Fleischmann, Thomas; Kohler, Hans-Peter E.; Kern, Susanne; Bleiner, Davide; Heeb, Norbert V.

doi:10.1016/j.chemosphere.2021.132939

Please use this identifier to cite or link to this item: https://doi.org/10.21256/zhaw-23886

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DC Field	Value	Language
dc.contributor.author	Knobloch, Marco C.	-
dc.contributor.author	Mathis, Flurin	-
dc.contributor.author	Fleischmann, Thomas	-
dc.contributor.author	Kohler, Hans-Peter E.	-
dc.contributor.author	Kern, Susanne	-
dc.contributor.author	Bleiner, Davide	-
dc.contributor.author	Heeb, Norbert V.	-
dc.date.accessioned	2022-01-12T14:42:18Z	-
dc.date.available	2022-01-12T14:42:18Z	-
dc.date.issued	2021-11-18	-
dc.identifier.issn	0045-6535	de_CH
dc.identifier.issn	1879-1298	de_CH
dc.identifier.uri	https://digitalcollection.zhaw.ch/handle/11475/23886	-
dc.description.abstract	Transformation studies of chlorinated paraffins (CPs) and the effects of CP transformation products on humans, biota and environment are rare. The focus here is on hydroxylation reactions. As for polyhalogenated persistent organic pollutants (POPs) in general, hydroxylation reactions convert lipophilic material to more polar compounds with increased mobility. We investigated the in-vitro transformation of single-chain CP-mixtures to hydroxylated products with the dehalogenase LinB from Sphingobium indicum. C11-, C12- and C13-single-chain CP-homologues were exposed to LinB and mono-hydroxylated (CP-ols) and di-hydroxylated (CP-diols) transformation products were formed. Liquid-chromatography coupled to mass-spectrometry (LC-MS) was used to detect hydroxylated products and to separate them from the starting material. The presented data can be used to identify these CP-ol and CP-diol homologues in other samples. Hydroxylated products had lower chlorination degrees (nCl) than respective CP-starting-materials. Reactive and persistent CP-material was found in each homologue group. Reactive material is converted within hours by LinB, while more persistent CPs are transformed within days. Homologue-specific kinetic models were established to simulate the stepwise hydroxylation of persistent CPs to mono- and di-hydroxylated products. First-order rate constants for the formation of CP-ols (k1) and CP-diols (k2) were deduced for different homologues. Lower-chlorinated CP-ols did not accumulate to large extent and were transformed quickly to CP-diols, while higher-chlorinated CP-ols and -diols both accumulated. By enzymatic transformation of single-chain CPs with LinB, we synthesized unique sets of mono- and di-hydroxylated materials, which can be used as analytical standards and as starting materials for metabolic, toxicity and environmental fate studies.	de_CH
dc.language.iso	en	de_CH
dc.publisher	Elsevier	de_CH
dc.relation.ispartof	Chemosphere	de_CH
dc.rights	http://creativecommons.org/licenses/by/4.0/	de_CH
dc.subject	Dihydroxylated chloroparaffins (CP-diols)	de_CH
dc.subject	Enzymatic dehalohydroxylation	de_CH
dc.subject	Hydroxylated chloroparaffins (CP-ols)	de_CH
dc.subject	In-vitro CP transformation	de_CH
dc.subject	Persistent organic pollutants (POPs)	de_CH
dc.subject.ddc	540: Chemie	de_CH
dc.title	Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum	de_CH
dc.type	Beitrag in wissenschaftlicher Zeitschrift	de_CH
dcterms.type	Text	de_CH
zhaw.departement	Life Sciences und Facility Management	de_CH
zhaw.organisationalunit	Institut für Chemie und Biotechnologie (ICBT)	de_CH
dc.identifier.doi	10.1016/j.chemosphere.2021.132939	de_CH
dc.identifier.doi	10.21256/zhaw-23886	-
dc.identifier.pmid	34800506	de_CH
zhaw.funding.eu	No	de_CH
zhaw.issue	132939	de_CH
zhaw.originated.zhaw	Yes	de_CH
zhaw.publication.status	publishedVersion	de_CH
zhaw.volume	291, Part 2	de_CH
zhaw.publication.review	Peer review (Publikation)	de_CH
zhaw.author.additional	No	de_CH
zhaw.display.portrait	Yes	de_CH
Appears in collections:	Publikationen Life Sciences und Facility Management

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Knobloch, M. C., Mathis, F., Fleischmann, T., Kohler, H.-P. E., Kern, S., Bleiner, D., & Heeb, N. V. (2021). Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum. Chemosphere, 291, Part 2(132939). https://doi.org/10.1016/j.chemosphere.2021.132939

Knobloch, M.C. et al. (2021) ‘Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum’, Chemosphere, 291, Part 2(132939). Available at: https://doi.org/10.1016/j.chemosphere.2021.132939.

M. C. Knobloch et al., “Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum,” Chemosphere, vol. 291, Part 2, no. 132939, Nov. 2021, doi: 10.1016/j.chemosphere.2021.132939.

KNOBLOCH, Marco C., Flurin MATHIS, Thomas FLEISCHMANN, Hans-Peter E. KOHLER, Susanne KERN, Davide BLEINER und Norbert V. HEEB, 2021. Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium indicum. Chemosphere. 18 November 2021. Bd. 291, Part 2, Nr. 132939. DOI 10.1016/j.chemosphere.2021.132939

Knobloch, Marco C., Flurin Mathis, Thomas Fleischmann, Hans-Peter E. Kohler, Susanne Kern, Davide Bleiner, and Norbert V. Heeb. 2021. “Enzymatic Synthesis and Formation Kinetics of Mono- and Di-Hydroxylated Chlorinated Paraffins with the Bacterial Dehalogenase LinB from Sphingobium Indicum.” Chemosphere 291, Part 2 (132939). https://doi.org/10.1016/j.chemosphere.2021.132939.

Knobloch, Marco C., et al. “Enzymatic Synthesis and Formation Kinetics of Mono- and Di-Hydroxylated Chlorinated Paraffins with the Bacterial Dehalogenase LinB from Sphingobium Indicum.” Chemosphere, vol. 291, Part 2, no. 132939, Nov. 2021, https://doi.org/10.1016/j.chemosphere.2021.132939.