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A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol

The earthy odor of geosmin with a C(12) skeleton is known from bacteria, fungi and plants. The sesquiterpenoid germacradien-11-ol (germacradienol) is a crucial intermediate in the biosynthesis of geosmin. A bifunctional terpene cyclase for germacradienol formation and its degradation to geosmin had...

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Autores principales: Peter, Marlies, Yang, Yiling, Li, Shu-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9527937/
https://www.ncbi.nlm.nih.gov/pubmed/36320281
http://dx.doi.org/10.1039/d2ra05033a
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author Peter, Marlies
Yang, Yiling
Li, Shu-Ming
author_facet Peter, Marlies
Yang, Yiling
Li, Shu-Ming
author_sort Peter, Marlies
collection PubMed
description The earthy odor of geosmin with a C(12) skeleton is known from bacteria, fungi and plants. The sesquiterpenoid germacradien-11-ol (germacradienol) is a crucial intermediate in the biosynthesis of geosmin. A bifunctional terpene cyclase for germacradienol formation and its degradation to geosmin had been described in bacteria. Terpene cyclases were also suggested for geosmin formation in basidiomycetes, but not reported for ascomycetes. We identified a putative terpene cyclase in Aspergillus ustus with low sequence homology to N-termini of the bacterial germacradienol/geosmin synthases. Heterologous expression in Aspergillus nidulans and biochemical characterization led to the identification of the geosmin precursor germacradienol as the sole detected enzyme product. Germacradienol synthase (GdlS) uses strictly farnesyl diphosphate as substrate for cyclization and requires Mg(2+) for its reaction. Multiple sequence alignments with known enzymes indicate the presence of the highly conserved catalytic residues including the DDXXD motif for Mg(2+) binding. Phylogenetic analysis suggests different clades of bacterial germacradienol/geosmin synthases and terpene cyclases from fungi.
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spelling pubmed-95279372022-10-31 A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol Peter, Marlies Yang, Yiling Li, Shu-Ming RSC Adv Chemistry The earthy odor of geosmin with a C(12) skeleton is known from bacteria, fungi and plants. The sesquiterpenoid germacradien-11-ol (germacradienol) is a crucial intermediate in the biosynthesis of geosmin. A bifunctional terpene cyclase for germacradienol formation and its degradation to geosmin had been described in bacteria. Terpene cyclases were also suggested for geosmin formation in basidiomycetes, but not reported for ascomycetes. We identified a putative terpene cyclase in Aspergillus ustus with low sequence homology to N-termini of the bacterial germacradienol/geosmin synthases. Heterologous expression in Aspergillus nidulans and biochemical characterization led to the identification of the geosmin precursor germacradienol as the sole detected enzyme product. Germacradienol synthase (GdlS) uses strictly farnesyl diphosphate as substrate for cyclization and requires Mg(2+) for its reaction. Multiple sequence alignments with known enzymes indicate the presence of the highly conserved catalytic residues including the DDXXD motif for Mg(2+) binding. Phylogenetic analysis suggests different clades of bacterial germacradienol/geosmin synthases and terpene cyclases from fungi. The Royal Society of Chemistry 2022-10-03 /pmc/articles/PMC9527937/ /pubmed/36320281 http://dx.doi.org/10.1039/d2ra05033a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Peter, Marlies
Yang, Yiling
Li, Shu-Ming
A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title_full A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title_fullStr A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title_full_unstemmed A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title_short A terpene cyclase from Aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
title_sort terpene cyclase from aspergillus ustus is involved in the biosynthesis of geosmin precursor germacradienol
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9527937/
https://www.ncbi.nlm.nih.gov/pubmed/36320281
http://dx.doi.org/10.1039/d2ra05033a
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