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Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin

Pathways by which the biopolymer lignin is broken down by soil microbes could be used to engineer new biocatalytic routes from lignin to renewable chemicals, but are currently not fully understood. In order to probe these pathways, we have prepared synthetic lignins containing (13)C at the sidechain...

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Autores principales: Alruwaili, Awatif, Rashid, Goran M. M., Sodré, Victoria, Mason, James, Rehman, Zainab, Menakath, Anjali K., Cheung, David, Brown, Steven P., Bugg, Timothy D. H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: RSC 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9811514/
https://www.ncbi.nlm.nih.gov/pubmed/36685258
http://dx.doi.org/10.1039/d2cb00173j
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author Alruwaili, Awatif
Rashid, Goran M. M.
Sodré, Victoria
Mason, James
Rehman, Zainab
Menakath, Anjali K.
Cheung, David
Brown, Steven P.
Bugg, Timothy D. H.
author_facet Alruwaili, Awatif
Rashid, Goran M. M.
Sodré, Victoria
Mason, James
Rehman, Zainab
Menakath, Anjali K.
Cheung, David
Brown, Steven P.
Bugg, Timothy D. H.
author_sort Alruwaili, Awatif
collection PubMed
description Pathways by which the biopolymer lignin is broken down by soil microbes could be used to engineer new biocatalytic routes from lignin to renewable chemicals, but are currently not fully understood. In order to probe these pathways, we have prepared synthetic lignins containing (13)C at the sidechain β-carbon. Feeding of [β-(13)C]-labelled DHP lignin to Rhodococcus jostii RHA1 has led to the incorporation of (13)C label into metabolites oxalic acid, 4-hydroxyphenylacetic acid, and 4-hydroxy-3-methoxyphenylacetic acid, confirming that they are derived from lignin breakdown. We have identified a glycolate oxidase enzyme in Rhodococcus jostii RHA1 which is able to oxidise glycolaldehyde via glycolic acid to oxalic acid, thereby identifying a pathway for the formation of oxalic acid. R. jostii glycolate oxidase also catalyses the conversion of 4-hydroxyphenylacetic acid to 4-hydroxybenzoylformic acid, identifying another possible pathway to 4-hydroxybenzoylformic acid. Formation of labelled oxalic acid was also observed from [β-(13)C]-polyferulic acid, which provides experimental evidence in favour of a radical mechanism for α,β-bond cleavage of β-aryl ether units.
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spelling pubmed-98115142023-01-20 Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin Alruwaili, Awatif Rashid, Goran M. M. Sodré, Victoria Mason, James Rehman, Zainab Menakath, Anjali K. Cheung, David Brown, Steven P. Bugg, Timothy D. H. RSC Chem Biol Chemistry Pathways by which the biopolymer lignin is broken down by soil microbes could be used to engineer new biocatalytic routes from lignin to renewable chemicals, but are currently not fully understood. In order to probe these pathways, we have prepared synthetic lignins containing (13)C at the sidechain β-carbon. Feeding of [β-(13)C]-labelled DHP lignin to Rhodococcus jostii RHA1 has led to the incorporation of (13)C label into metabolites oxalic acid, 4-hydroxyphenylacetic acid, and 4-hydroxy-3-methoxyphenylacetic acid, confirming that they are derived from lignin breakdown. We have identified a glycolate oxidase enzyme in Rhodococcus jostii RHA1 which is able to oxidise glycolaldehyde via glycolic acid to oxalic acid, thereby identifying a pathway for the formation of oxalic acid. R. jostii glycolate oxidase also catalyses the conversion of 4-hydroxyphenylacetic acid to 4-hydroxybenzoylformic acid, identifying another possible pathway to 4-hydroxybenzoylformic acid. Formation of labelled oxalic acid was also observed from [β-(13)C]-polyferulic acid, which provides experimental evidence in favour of a radical mechanism for α,β-bond cleavage of β-aryl ether units. RSC 2022-11-24 /pmc/articles/PMC9811514/ /pubmed/36685258 http://dx.doi.org/10.1039/d2cb00173j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Alruwaili, Awatif
Rashid, Goran M. M.
Sodré, Victoria
Mason, James
Rehman, Zainab
Menakath, Anjali K.
Cheung, David
Brown, Steven P.
Bugg, Timothy D. H.
Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title_full Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title_fullStr Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title_full_unstemmed Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title_short Elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
title_sort elucidation of microbial lignin degradation pathways using synthetic isotope-labelled lignin
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9811514/
https://www.ncbi.nlm.nih.gov/pubmed/36685258
http://dx.doi.org/10.1039/d2cb00173j
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