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dc.contributor.authorHeeb, Norbert V.-
dc.contributor.authorZindel, Daniel-
dc.contributor.authorGraf, Heidi-
dc.contributor.authorAzara, Valeria-
dc.contributor.authorBernd Schweizer, W.-
dc.contributor.authorGeueke, Birgit-
dc.contributor.authorKohler, Hans-Peter E.-
dc.contributor.authorLienemann, Peter-
dc.date.accessioned2018-11-16T10:05:30Z-
dc.date.available2018-11-16T10:05:30Z-
dc.date.issued2013-
dc.identifier.issn0045-6535de_CH
dc.identifier.issn1879-1298de_CH
dc.identifier.urihttps://digitalcollection.zhaw.ch/handle/11475/12903-
dc.description.abstractThe haloalkane dehalogenase LinB from Sphingobium indicum B90A converts β-hexachlorocyclohexane (β-HCH), the most persistent HCH stereoisomer, to mono- and dihydroxylated metabolites. Recently, we reported that LinB also transforms α-, β- and γ-hexabromocyclododecanes (HBCDs), which are structurally related to HCHs. Here, we show that LinB catalyzes the hydroxylation of δ-HBCD to two pentabromocyclododecanols (PBCDOHs) and two tetrabromocyclododecadiols (TBCDDOHs). The stereochemistry of this enzymatic transformation was deduced from XRD crystal structure data of the substrate δ-HBCD and α(2)-PBCDOH, one of the biotransformation products. Five stereocenters of δ-HBCD are unchanged but the one at C6 is converted to an alcohol with inversion from S- to R-configuration in a nucleophilic, S(N)2-like substitution reaction. Only α(2)-PBCDOH with the 1R,2R,5S,6R,9R,10S-configuration is obtained but not its enantiomer. With only two of the 64 PBCDOHs formed, these transformations indeed are regio- and stereoselective. A conformational analysis revealed that the triple-turn motive, which is predominant in δ-HBCD and in several other HBCD stereoisomers, is also found in the product. This shows that LinB preferentially converted reactive bromine atoms but not those in the conserved triple-turn motive. The widespread contamination with HCHs triggered the bacterial evolution of dehalogenases which acquired the ability to convert these pollutants and their metabolites. We here demonstrate that LinB of S. indicum also transforms HBCDs regio- and stereoselectively following a similar mechanism.de_CH
dc.language.isoende_CH
dc.publisherElsevierde_CH
dc.relation.ispartofChemospherede_CH
dc.rightsLicence according to publishing contractde_CH
dc.subjectCatalysisde_CH
dc.subjectBrominated hydrocarbonsde_CH
dc.subjectNucleotidyltransferasesde_CH
dc.subjectSoil Pollutantsde_CH
dc.subjectSphingomonadaceaede_CH
dc.subjectStereoisomerismde_CH
dc.subjectBiotransformationde_CH
dc.subject.ddc572: Biochemiede_CH
dc.titleStereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanolde_CH
dc.typeBeitrag in wissenschaftlicher Zeitschriftde_CH
dcterms.typeTextde_CH
zhaw.departementLife Sciences und Facility Managementde_CH
zhaw.organisationalunitInstitut für Chemie und Biotechnologie (ICBT)de_CH
dc.identifier.doi10.1016/j.chemosphere.2012.10.019de_CH
dc.identifier.pmid23177717de_CH
zhaw.funding.euNode_CH
zhaw.issue6de_CH
zhaw.originated.zhawYesde_CH
zhaw.pages.end1919de_CH
zhaw.pages.start1911de_CH
zhaw.publication.statuspublishedVersionde_CH
zhaw.volume90de_CH
zhaw.publication.reviewPeer review (Publikation)de_CH
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Heeb, N. V., Zindel, D., Graf, H., Azara, V., Bernd Schweizer, W., Geueke, B., Kohler, H.-P. E., & Lienemann, P. (2013). Stereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanol. Chemosphere, 90(6), 1911–1919. https://doi.org/10.1016/j.chemosphere.2012.10.019
Heeb, N.V. et al. (2013) ‘Stereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanol’, Chemosphere, 90(6), pp. 1911–1919. Available at: https://doi.org/10.1016/j.chemosphere.2012.10.019.
N. V. Heeb et al., “Stereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanol,” Chemosphere, vol. 90, no. 6, pp. 1911–1919, 2013, doi: 10.1016/j.chemosphere.2012.10.019.
HEEB, Norbert V., Daniel ZINDEL, Heidi GRAF, Valeria AZARA, W. BERND SCHWEIZER, Birgit GEUEKE, Hans-Peter E. KOHLER und Peter LIENEMANN, 2013. Stereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanol. Chemosphere. 2013. Bd. 90, Nr. 6, S. 1911–1919. DOI 10.1016/j.chemosphere.2012.10.019
Heeb, Norbert V., Daniel Zindel, Heidi Graf, Valeria Azara, W. Bernd Schweizer, Birgit Geueke, Hans-Peter E. Kohler, and Peter Lienemann. 2013. “Stereochemistry of LinB-Catalyzed Biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-Pentabromocyclododecanol.” Chemosphere 90 (6): 1911–19. https://doi.org/10.1016/j.chemosphere.2012.10.019.
Heeb, Norbert V., et al. “Stereochemistry of LinB-Catalyzed Biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-Pentabromocyclododecanol.” Chemosphere, vol. 90, no. 6, 2013, pp. 1911–19, https://doi.org/10.1016/j.chemosphere.2012.10.019.


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