Mostra el registre d'ítem simple
Comprehensive insights into the production of long chain aliphatic aldehydes using a copper-radical alcohol oxidase as biocatalyst
dc.contributor.author | Ribeaucourt, David |
dc.contributor.author | Bissaro, Bastien |
dc.contributor.author | Guallar, Victor |
dc.contributor.author | Yemloul, Mehdi |
dc.contributor.author | Haon, Mireille |
dc.contributor.author | Grisel, Sacha |
dc.contributor.author | Alphand, Véronique |
dc.contributor.author | Brumer, Harry |
dc.contributor.author | Lambert, Fanny |
dc.contributor.author | Berrin, Jean-Guy |
dc.contributor.author | Lafond, Mickael |
dc.contributor.other | Barcelona Supercomputing Center |
dc.date.accessioned | 2021-03-19T11:42:08Z |
dc.date.available | 2022-03-11T01:25:29Z |
dc.date.issued | 2021 |
dc.identifier.citation | Ribeaucourt, D. [et al.]. Comprehensive insights into the production of long chain aliphatic aldehydes using a copper-radical alcohol oxidase as biocatalyst. "ACS Sustainable Chemistry & Engineering", 2021, |
dc.identifier.issn | 2168-0485 |
dc.identifier.uri | http://hdl.handle.net/2117/342066 |
dc.description.abstract | The oxidation of alcohols is a cornerstone reaction in chemistry, notably in the flavor and fragrance industry where long-chain aliphatic aldehydes are major odorant compounds. In a context where greener alternatives are sought after, biocatalysis holds many promises. Here, we investigated the ability of the alcohol oxidase from Colletotrichum graminicola (CgrAlcOx)—an organic cofactor-free enzyme belonging to the copper-radical oxidase (CRO) class—to convert industrially relevant long-chain aliphatic alcohols. CgrAlcOx is a competent catalyst for the conversion of octan-1-ol when supported by the accessory enzymes peroxidase and catalase. Detailed examination of the products revealed the occurrence of an overoxidation step leading to the production of carboxylic acid for some aliphatic aldehydes and benzaldehyde derivatives. The partition between aldehyde and acid products varied upon substrate properties (chain length and propensity to form geminal-diols) and enzyme specificity and could be tuned by controlling the reaction conditions. In silico analyses suggested an inhibitory binding mode of long-chain aliphatic geminal-diols and a substrate-induced fit mechanism for a benzyl alcohol derivative. By demonstrating their natural ability to perform long-chain aliphatic alcohol oxidation, the present study establishes the potential of fungal CRO-AlcOx as promising candidates for the green production of flavor and fragrance compounds. |
dc.description.sponsorship | This study was supported by the French National Agency for Research (“Agence Nationale de la Recherche”) through the “Projet de Recherche Collaboratif International” ANR-NSERC (FUNTASTIC project, ANR-17-CE07-0047), by the Natural Sciences and Engineering Research Council of Canada through the "Strategic Projects - Natural Resources and Energy - Project (STPGP) entitled "FUNTASTIC - Fungal copper-radical oxidases as new biocatalysts for the valorization of biomass carbohydrates and alcohols" and by the PID2019-106370RB-I00 grant from the Spanish Ministry of Innovation and Sciences. We are grateful to MANE & Fils and the “Association Nationale Recherche Technologie” (ANRT) for funding the PhD fellowship of D.R. entitled “Discovery and structure-function study of new fungal copper radicals oxidases used as biocatalysts for the valorisation of alcohols and plant biomass.” This Convention Industrielle de Formation par la RecherchE (CIFRE) grant no. 2017/1169 runs from 1 April 2018 to 1 April 2021 |
dc.format.extent | 11 p. |
dc.language.iso | eng |
dc.publisher | American Chemical Society |
dc.relation.uri | https://pubs.acs.org/doi/10.1021/acssuschemeng.0c07406 |
dc.subject | Àrees temàtiques de la UPC::Enginyeria química |
dc.subject.lcsh | Chemistry |
dc.subject.lcsh | Aliphatic compounds |
dc.subject.lcsh | Biocatalysts |
dc.subject.other | Biocatalysts |
dc.subject.other | Copper-radical oxidases |
dc.subject.other | Alcohol oxidases |
dc.subject.other | Long-chain aliphatic alcohols |
dc.subject.other | Fragrant aldehydes |
dc.title | Comprehensive insights into the production of long chain aliphatic aldehydes using a copper-radical alcohol oxidase as biocatalyst |
dc.type | Article |
dc.subject.lemac | Química |
dc.identifier.doi | 10.1021/acscatal.0c03165 |
dc.description.peerreviewed | Peer Reviewed |
dc.rights.access | Open Access |
dc.description.version | Postprint (author's final draft) |
local.citation.publicationName | ACS Sustainable Chemistry & Engineering |
Fitxers d'aquest items
Aquest ítem apareix a les col·leccions següents
-
Articles de revista [374]