Late-Stage Functionalisation of Polycyclic (N-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus Polyporus arcularius

Functionalisation of polycyclic aromatic hydrocarbons (PAHs) and their N-heteroarene analogues (NPAHs) is a tedious synthetic endeavour that requires diverse bottom-up approaches. Cytochrome P450 enzymes of white-rot fungi were shown to participate in the fungal detoxification of...

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Autores principales:	Nico D. Fessner, Christopher Grimm, Wolfgang Kroutil, Anton Glieder
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>P. arcularius</i> late-stage functionalisation CYP5035 detoxification polycyclic aromatic hydrocarbons Microbiology QR1-502
Acceso en línea:	https://doaj.org/article/5d010a7247fa4d81a0fa9ec8a5e5cf89
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spelling	oai:doaj.org-article:5d010a7247fa4d81a0fa9ec8a5e5cf892021-11-25T16:54:05ZLate-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>10.3390/biom111117082218-273Xhttps://doaj.org/article/5d010a7247fa4d81a0fa9ec8a5e5cf892021-11-01T00:00:00Zhttps://www.mdpi.com/2218-273X/11/11/1708https://doaj.org/toc/2218-273XFunctionalisation of polycyclic aromatic hydrocarbons (PAHs) and their <i>N</i>-heteroarene analogues (NPAHs) is a tedious synthetic endeavour that requires diverse bottom-up approaches. Cytochrome P450 enzymes of white-rot fungi were shown to participate in the fungal detoxification of xenobiotics and environmental hazards via hydroxylation of PAH compounds. In this paper, the recently discovered activity of the monooxygenase CYP5035S7 towards (N)PAHs was investigated in detail, and products formed from the substrates azulene, acenaphthene, fluorene, anthracene, and phenanthrene by whole-cell biocatalysis were isolated and characterised. The observed regioselectivity of CYP5035S7 could be explained by a combination of the substrate’s electron density and steric factors influencing the substrate orientation giving insight into the active-site geometry of the enzyme.Nico D. FessnerChristopher GrimmWolfgang KroutilAnton GliederMDPI AGarticle<i>P. arcularius</i>late-stage functionalisationCYP5035detoxificationpolycyclic aromatic hydrocarbonsMicrobiologyQR1-502ENBiomolecules, Vol 11, Iss 1708, p 1708 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>P. arcularius</i> late-stage functionalisation CYP5035 detoxification polycyclic aromatic hydrocarbons Microbiology QR1-502
spellingShingle	<i>P. arcularius</i> late-stage functionalisation CYP5035 detoxification polycyclic aromatic hydrocarbons Microbiology QR1-502 Nico D. Fessner Christopher Grimm Wolfgang Kroutil Anton Glieder Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
description	Functionalisation of polycyclic aromatic hydrocarbons (PAHs) and their <i>N</i>-heteroarene analogues (NPAHs) is a tedious synthetic endeavour that requires diverse bottom-up approaches. Cytochrome P450 enzymes of white-rot fungi were shown to participate in the fungal detoxification of xenobiotics and environmental hazards via hydroxylation of PAH compounds. In this paper, the recently discovered activity of the monooxygenase CYP5035S7 towards (N)PAHs was investigated in detail, and products formed from the substrates azulene, acenaphthene, fluorene, anthracene, and phenanthrene by whole-cell biocatalysis were isolated and characterised. The observed regioselectivity of CYP5035S7 could be explained by a combination of the substrate’s electron density and steric factors influencing the substrate orientation giving insight into the active-site geometry of the enzyme.
format	article
author	Nico D. Fessner Christopher Grimm Wolfgang Kroutil Anton Glieder
author_facet	Nico D. Fessner Christopher Grimm Wolfgang Kroutil Anton Glieder
author_sort	Nico D. Fessner
title	Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
title_short	Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
title_full	Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
title_fullStr	Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
title_full_unstemmed	Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>
title_sort	late-stage functionalisation of polycyclic (<i>n</i>-hetero-) aromatic hydrocarbons by detoxifying cyp5035s7 monooxygenase of the white-rot fungus <i>polyporus arcularius</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/5d010a7247fa4d81a0fa9ec8a5e5cf89
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Late-Stage Functionalisation of Polycyclic (<i>N</i>-Hetero-) Aromatic Hydrocarbons by Detoxifying CYP5035S7 Monooxygenase of the White-Rot Fungus <i>Polyporus arcularius</i>

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