Artículo
Albumin-catalysed synthesis of flavanones
Fecha de publicación:
02/2023
Editorial:
Elsevier
Revista:
Process Biochemistry
ISSN:
1359-5113
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
Flavanones are a family of phytochemicals that have regained importance over the last decade due to their diverse biological activity. The conventional building of the flavanone skeleton is accomplished through a Claisen-Schmidt condensation followed by an intramolecular oxa-Michael addition, but the involved strong basic pH favours side reactions and affects flavanone yield. This work presents a mild access to flavanones based on a sustainable catalyst, bovine serum albumin (BSA), which is a promiscuous protein. BSA catalysed the reaction between a set of 2 ´ -hydroxyacetophenones and benzaldehydes in methanol at 60 °C to give the corresponding flavanones in 58–90% conversions. Experiments showed that BSA promotes the Claisen-Schmidt step as well as accelerates the subsequent oxa-Michael addition. Besides, BSA-catalysed reaction of acetophenone and benzaldehyde was studied, which afforded the Michael adduct 1,3,5-triphenylpentane-1,5-dione (85% conversion). On the whole, the herein reported results expand the potential of BSA as a mild and sustainable catalyst in organic synthesis.
Palabras clave:
ALBUMIN
,
BIOCATALYSIS
,
FLAVANONES
,
PROMISCUITY
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Colecciones
Articulos(SEDE CENTRAL)
Articulos de SEDE CENTRAL
Articulos de SEDE CENTRAL
Citación
Borucki, Estefanía Lorena; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; Albumin-catalysed synthesis of flavanones; Elsevier; Process Biochemistry; 125; 2-2023; 1-6
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