PMID- 34800506
OWN - NLM
STAT- MEDLINE
DCOM- 20220126
LR  - 20220126
IS  - 1879-1298 (Electronic)
IS  - 0045-6535 (Linking)
VI  - 291
IP  - Pt 2
DP  - 2022 Mar
TI  - Enzymatic synthesis and formation kinetics of mono- and di-hydroxylated 
      chlorinated paraffins with the bacterial dehalogenase LinB from Sphingobium 
      indicum.
PG  - 132939
LID - S0045-6535(21)03411-1 [pii]
LID - 10.1016/j.chemosphere.2021.132939 [doi]
AB  - 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. C(11)-, C(12)- and C(13)-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 (n(Cl)) 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 (k(1)) and CP-diols (k(2)) 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.
CI  - Copyright (c) 2021 The Authors. Published by Elsevier Ltd.. All rights reserved.
FAU - Knobloch, Marco C
AU  - Knobloch MC
AD  - Laboratory for Advanced Analytical Technologies, Swiss Federal Institute for 
      Materials Science and Technology Empa, Uberlandstrasse 129, 8600, Dubendorf, 
      Switzerland; Department of Chemistry, University of Zurich, Winterthurerstrasse 
      190, 8057, Zurich, Switzerland. Electronic address: marco.knobloch@empa.ch.
FAU - Mathis, Flurin
AU  - Mathis F
AD  - Laboratory for Advanced Analytical Technologies, Swiss Federal Institute for 
      Materials Science and Technology Empa, Uberlandstrasse 129, 8600, Dubendorf, 
      Switzerland; Zurich University of Applied Sciences ZHAW, Einsiedlerstrasse 31, 
      8820, Wadenswil, Switzerland.
FAU - Fleischmann, Thomas
AU  - Fleischmann T
AD  - Swiss Federal Institute of Aquatic Research and Technology Eawag, Uberlandstrasse 
      129, 8600, Dubendorf, Switzerland.
FAU - Kohler, Hans-Peter E
AU  - Kohler HE
AD  - Swiss Federal Institute of Aquatic Research and Technology Eawag, Uberlandstrasse 
      129, 8600, Dubendorf, Switzerland.
FAU - Kern, Susanne
AU  - Kern S
AD  - Zurich University of Applied Sciences ZHAW, Einsiedlerstrasse 31, 8820, 
      Wadenswil, Switzerland.
FAU - Bleiner, Davide
AU  - Bleiner D
AD  - Laboratory for Advanced Analytical Technologies, Swiss Federal Institute for 
      Materials Science and Technology Empa, Uberlandstrasse 129, 8600, Dubendorf, 
      Switzerland; Department of Chemistry, University of Zurich, Winterthurerstrasse 
      190, 8057, Zurich, Switzerland.
FAU - Heeb, Norbert V
AU  - Heeb NV
AD  - Laboratory for Advanced Analytical Technologies, Swiss Federal Institute for 
      Materials Science and Technology Empa, Uberlandstrasse 129, 8600, Dubendorf, 
      Switzerland.
LA  - eng
PT  - Journal Article
DEP - 20211118
PL  - England
TA  - Chemosphere
JT  - Chemosphere
JID - 0320657
RN  - 0 (Hydrocarbons, Chlorinated)
RN  - 8002-74-2 (Paraffin)
RN  - Sphingobium indicum
SB  - IM
MH  - Environmental Monitoring
MH  - Halogenation
MH  - Humans
MH  - *Hydrocarbons, Chlorinated/analysis
MH  - Kinetics
MH  - Paraffin/analysis
MH  - *Sphingomonadaceae
OTO - NOTNLM
OT  - Dihydroxylated chloroparaffins (CP-diols)
OT  - Enzymatic dehalohydroxylation
OT  - Hydroxylated chloroparaffins (CP-ols)
OT  - In-vitro CP transformation
OT  - Persistent organic pollutants (POPs)
EDAT- 2021/11/21 06:00
MHDA- 2022/01/27 06:00
CRDT- 2021/11/20 20:10
PHST- 2021/06/27 00:00 [received]
PHST- 2021/11/11 00:00 [revised]
PHST- 2021/11/14 00:00 [accepted]
PHST- 2021/11/21 06:00 [pubmed]
PHST- 2022/01/27 06:00 [medline]
PHST- 2021/11/20 20:10 [entrez]
AID - S0045-6535(21)03411-1 [pii]
AID - 10.1016/j.chemosphere.2021.132939 [doi]
PST - ppublish
SO  - Chemosphere. 2022 Mar;291(Pt 2):132939. doi: 10.1016/j.chemosphere.2021.132939. 
      Epub 2021 Nov 18.