Biotransformation of Hexabromocyclododecanes (HBCDs) with LinB--an HCH-converting bacterial enzyme

Environmental Science & Technology
Norbert V HeebPeter Lienemann

Abstract

Hexabromocyclododecanes (HBCDs) and hexachlorocyclohexanes (HCHs) are polyhalogenated hydrocarbons with similar stereochemistry. Both classes of compounds are considered biologically persistent and bioaccumulating pollutants. In 2009, the major HCH stereoisomers came under regulation of the Stockholm convention. Despite their persistence, HCHs are susceptible to bacterial biotransformations. Here we show that LinB, an HCH-converting haloalkane dehalogenase from Sphingobium indicum B90A, is also able to transform HBCDs. Racemic mixtures of α-, β-, and γ-HBCDs were exposed to LinB under various conditions. All stereoisomers were converted, but (-)α-, (+)β-, and (+)γ-HBCDs were transformed faster by LinB than their enantiomers. The enantiomeric excess increased to 8 ± 4%, 27 ± 1%, and 20 ± 2% in 32 h comparable to values of 7.1%, 27.0%, and 22.9% as obtained from respective kinetic models. Initially formed pentabromocyclododecanols (PBCDOHs) were further transformed to tetrabromocyclododecadiols (TBCDDOHs). At least, seven mono- and five dihydroxylated products were distinguished by LC-MS so far. The widespread occurrence of HCHs has led to the evolution of bacterial degradation pathways for such compounds. It remains to be shown ...Continue Reading

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Citations

Jan 27, 2015·The Science of the Total Environment·D DrageS Harrad
Nov 13, 2015·The Journal of Physical Chemistry. B·Rabindra Nath MannaAgnieszka Dybala-Defratyka
Sep 12, 2012·Biotechnology Journal·Tana KoudelakovaJiri Damborsky
Mar 27, 2015·Environmental Toxicology and Chemistry·Da ChenRobert J Letcher
Sep 17, 2015·Applied Microbiology and Biotechnology·Yuji NagataMasataka Tsuda
Jan 22, 2014·Chemosphere·Norbert V HeebPeter Lienemann
Jun 7, 2016·The Science of the Total Environment·Silviu-Laurentiu BadeaEthel Eljarrat
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Jun 17, 2021·Applied and Environmental Microbiology·Ling HuangHongzhi Tang
Sep 27, 2020·Bulletin of Environmental Contamination and Toxicology·Hemen Sarma, Sanket J Joshi

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