Applications of biocatalytic C C bond reductions in the synthesis of flavours and fragrances

Abstract

Industrial biotechnology and biocatalysis can provide very effective synthetic tools to increase the sustainability of the production of fine chemicals, especially flavour and fragrance (F&F) ingredients, the market demand of which has been constantly increasing in the last years. One of the most important transformations in F&F chemistry is the reduction of CC bonds, typically carried out with metal-catalysed hydrogenations or hydride-based reagents. Its biocatalytic counterpart is a competitive alternative, showcasing a range of advantages such as excellent chemo-, regio- and stereoselectivity, ease of implementation, mild reaction conditions and modest environmental impact. In the present review, the application of biocatalysed alkene reductions (from microbial fermentations with wild-type strains to engineered isolated ene-reductase enzymes) to synthetic processes useful for the F&F industry will be described, highlighting not only the exquisite stereoselectivity achieved, but also the overall improvement when chirality is not involved. Multi-enzymatic cascades involving CC bioreductions are also examined, which allow much greater chemical complexity to be built in one-pot biocatalytic systems.

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Dettagli Bibliografici
Autori: Maria C. Cancellieri iD ORCID 0009-0000-8447-9351 (Politecnico di Milano); Celeste Nobbio iD ORCID 0009-0009-6141-6687 (Politecnico di Milano); Francesco Gilberto Gatti iD ORCID 0000-0003-0837-4616 (Politecnico di Milano); Elisabetta Brenna iD ORCID 0000-0002-1315-7248 (Politecnico di Milano); Fabio Parmeggiani iD ORCID 0000-0001-5861-9269 (Politecnico di Milano)
Pubblicato in: Journal of Biotechnology, vol. 390, pp. 13-27
Data di pubblicazione:16/05/2024
Editore:Elsevier BV
Tipo di documento:Articolo
Lingua:inglese
DOI: 10.1016/j.jbiotec.2024.05.006
ISSN:0168-1656, 1873-4863
Accesso aperto: Accesso aperto Ibrido: articolo aperto in una rivista in abbonamento – Journal of Biotechnology (licenza: CC-BY, versione editoriale)
Citazioni ricevute:12
Soggetti:
Enzyme Catalysis and Immobilization (Life Sciences > Biochemistry, Genetics and Molecular Biology > Molecular Biology)
Biochemical and biochemical processes (Life Sciences > Biochemistry, Genetics and Molecular Biology > Biotechnology)
Asymmetric Hydrogenation and Catalysis (Physical Sciences > Chemistry > Inorganic Chemistry)
Identificativi: OpenAlex W4396951444 · PMID 38761886

Dati dell'indice centrale: OpenAlex (licenza CC0).

Descrizione
Riassunto:Industrial biotechnology and biocatalysis can provide very effective synthetic tools to increase the sustainability of the production of fine chemicals, especially flavour and fragrance (F&F) ingredients, the market demand of which has been constantly increasing in the last years. One of the most important transformations in F&F chemistry is the reduction of CC bonds, typically carried out with metal-catalysed hydrogenations or hydride-based reagents. Its biocatalytic counterpart is a competitive alternative, showcasing a range of advantages such as excellent chemo-, regio- and stereoselectivity, ease of implementation, mild reaction conditions and modest environmental impact. In the present review, the application of biocatalysed alkene reductions (from microbial fermentations with wild-type strains to engineered isolated ene-reductase enzymes) to synthetic processes useful for the F&F industry will be described, highlighting not only the exquisite stereoselectivity achieved, but also the overall improvement when chirality is not involved. Multi-enzymatic cascades involving CC bioreductions are also examined, which allow much greater chemical complexity to be built in one-pot biocatalytic systems.
ISSN:0168-1656
1873-4863
DOI:10.1016/j.jbiotec.2024.05.006