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Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134

2,4,5-TCP 4-monooxygenase (TftD) and 2,4,6-TCP 4-monooxygenase (TcpA) have been discovered in the biodegradation of 2,4,5-trichlorophenol (2,4,5-TCP) and 2,4,6-trichlorophenol (2,4,6-TCP). TcpA and TftD belong to the reduced flavin adenine dinucleotide (FADH(2))-dependent monooxygenases and both use...

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Autores principales: Hayes, Robert P., Webb, Brian N., Subramanian, Arun Kumar, Nissen, Mark, Popchock, Andrew, Xun, Luying, Kang, ChulHee
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International (MDPI) 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3431827/
https://www.ncbi.nlm.nih.gov/pubmed/22949829
http://dx.doi.org/10.3390/ijms13089769
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author Hayes, Robert P.
Webb, Brian N.
Subramanian, Arun Kumar
Nissen, Mark
Popchock, Andrew
Xun, Luying
Kang, ChulHee
author_facet Hayes, Robert P.
Webb, Brian N.
Subramanian, Arun Kumar
Nissen, Mark
Popchock, Andrew
Xun, Luying
Kang, ChulHee
author_sort Hayes, Robert P.
collection PubMed
description 2,4,5-TCP 4-monooxygenase (TftD) and 2,4,6-TCP 4-monooxygenase (TcpA) have been discovered in the biodegradation of 2,4,5-trichlorophenol (2,4,5-TCP) and 2,4,6-trichlorophenol (2,4,6-TCP). TcpA and TftD belong to the reduced flavin adenine dinucleotide (FADH(2))-dependent monooxygenases and both use 2,4,6-TCP as a substrate; however, the two enzymes produce different end products. TftD catalyzes a typical monooxygenase reaction, while TcpA catalyzes a typical monooxygenase reaction followed by a hydrolytic dechlorination. We have previously reported the 3D structure of TftD and confirmed the catalytic residue, His289. Here we have determined the crystal structure of TcpA and investigated the apparent differences in specificity and catalysis between these two closely related monooxygenases through structural comparison. Our computational docking results suggest that Ala293 in TcpA (Ile292 in TftD) is possibly responsible for the differences in substrate specificity between the two monooxygenases. We have also identified that Arg101 in TcpA could provide inductive effects/charge stabilization during hydrolytic dechlorination. The collective information provides a fundamental understanding of the catalytic reaction mechanism and the parameters for substrate specificity. The information may provide guidance for designing bioremediation strategies for polychlorophenols, a major group of environmental pollutants.
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spelling pubmed-34318272012-09-04 Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134 Hayes, Robert P. Webb, Brian N. Subramanian, Arun Kumar Nissen, Mark Popchock, Andrew Xun, Luying Kang, ChulHee Int J Mol Sci Article 2,4,5-TCP 4-monooxygenase (TftD) and 2,4,6-TCP 4-monooxygenase (TcpA) have been discovered in the biodegradation of 2,4,5-trichlorophenol (2,4,5-TCP) and 2,4,6-trichlorophenol (2,4,6-TCP). TcpA and TftD belong to the reduced flavin adenine dinucleotide (FADH(2))-dependent monooxygenases and both use 2,4,6-TCP as a substrate; however, the two enzymes produce different end products. TftD catalyzes a typical monooxygenase reaction, while TcpA catalyzes a typical monooxygenase reaction followed by a hydrolytic dechlorination. We have previously reported the 3D structure of TftD and confirmed the catalytic residue, His289. Here we have determined the crystal structure of TcpA and investigated the apparent differences in specificity and catalysis between these two closely related monooxygenases through structural comparison. Our computational docking results suggest that Ala293 in TcpA (Ile292 in TftD) is possibly responsible for the differences in substrate specificity between the two monooxygenases. We have also identified that Arg101 in TcpA could provide inductive effects/charge stabilization during hydrolytic dechlorination. The collective information provides a fundamental understanding of the catalytic reaction mechanism and the parameters for substrate specificity. The information may provide guidance for designing bioremediation strategies for polychlorophenols, a major group of environmental pollutants. Molecular Diversity Preservation International (MDPI) 2012-08-06 /pmc/articles/PMC3431827/ /pubmed/22949829 http://dx.doi.org/10.3390/ijms13089769 Text en © 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Hayes, Robert P.
Webb, Brian N.
Subramanian, Arun Kumar
Nissen, Mark
Popchock, Andrew
Xun, Luying
Kang, ChulHee
Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title_full Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title_fullStr Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title_full_unstemmed Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title_short Structural and Catalytic Differences between Two FADH(2)-Dependent Monooxygenases: 2,4,5-TCP 4-Monooxygenase (TftD) from Burkholderia cepacia AC1100 and 2,4,6-TCP 4-Monooxygenase (TcpA) from Cupriavidus necator JMP134
title_sort structural and catalytic differences between two fadh(2)-dependent monooxygenases: 2,4,5-tcp 4-monooxygenase (tftd) from burkholderia cepacia ac1100 and 2,4,6-tcp 4-monooxygenase (tcpa) from cupriavidus necator jmp134
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3431827/
https://www.ncbi.nlm.nih.gov/pubmed/22949829
http://dx.doi.org/10.3390/ijms13089769
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