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Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase

Aldehydes are a class of carbonyl compounds widely used as intermediates in the pharmaceutical, cosmetic and food industries. To date, there are few fully enzymatic methods for synthesizing these highly reactive chemicals. In the present work, we explore the biocatalytic potential of an amino oxidas...

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Autores principales: Di Fabio, Elisa, Incocciati, Alessio, Boffi, Alberto, Bonamore, Alessandra, Macone, Alberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8533949/
https://www.ncbi.nlm.nih.gov/pubmed/34680172
http://dx.doi.org/10.3390/biom11101540
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author Di Fabio, Elisa
Incocciati, Alessio
Boffi, Alberto
Bonamore, Alessandra
Macone, Alberto
author_facet Di Fabio, Elisa
Incocciati, Alessio
Boffi, Alberto
Bonamore, Alessandra
Macone, Alberto
author_sort Di Fabio, Elisa
collection PubMed
description Aldehydes are a class of carbonyl compounds widely used as intermediates in the pharmaceutical, cosmetic and food industries. To date, there are few fully enzymatic methods for synthesizing these highly reactive chemicals. In the present work, we explore the biocatalytic potential of an amino oxidase extracted from the etiolated shoots of Lathyrus cicera for the synthesis of value-added aldehydes, starting from the corresponding primary amines. In this frame, we have developed a completely chromatography-free purification protocol based on crossflow ultrafiltration, which makes the production of this enzyme easily scalable. Furthermore, we determined the kinetic parameters of the amine oxidase toward 20 differently substituted aliphatic and aromatic primary amines, and we developed a biocatalytic process for their conversion into the corresponding aldehydes. The reaction occurs in aqueous media at neutral pH in the presence of catalase, which removes the hydrogen peroxide produced during the reaction itself, contributing to the recycling of oxygen. A high conversion (>95%) was achieved within 3 h for all the tested compounds.
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spelling pubmed-85339492021-10-23 Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase Di Fabio, Elisa Incocciati, Alessio Boffi, Alberto Bonamore, Alessandra Macone, Alberto Biomolecules Article Aldehydes are a class of carbonyl compounds widely used as intermediates in the pharmaceutical, cosmetic and food industries. To date, there are few fully enzymatic methods for synthesizing these highly reactive chemicals. In the present work, we explore the biocatalytic potential of an amino oxidase extracted from the etiolated shoots of Lathyrus cicera for the synthesis of value-added aldehydes, starting from the corresponding primary amines. In this frame, we have developed a completely chromatography-free purification protocol based on crossflow ultrafiltration, which makes the production of this enzyme easily scalable. Furthermore, we determined the kinetic parameters of the amine oxidase toward 20 differently substituted aliphatic and aromatic primary amines, and we developed a biocatalytic process for their conversion into the corresponding aldehydes. The reaction occurs in aqueous media at neutral pH in the presence of catalase, which removes the hydrogen peroxide produced during the reaction itself, contributing to the recycling of oxygen. A high conversion (>95%) was achieved within 3 h for all the tested compounds. MDPI 2021-10-18 /pmc/articles/PMC8533949/ /pubmed/34680172 http://dx.doi.org/10.3390/biom11101540 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Di Fabio, Elisa
Incocciati, Alessio
Boffi, Alberto
Bonamore, Alessandra
Macone, Alberto
Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title_full Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title_fullStr Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title_full_unstemmed Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title_short Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase
title_sort biocatalytic production of aldehydes: exploring the potential of lathyrus cicera amine oxidase
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8533949/
https://www.ncbi.nlm.nih.gov/pubmed/34680172
http://dx.doi.org/10.3390/biom11101540
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