| Texto completo | |
| Autor(es): |
Silva, Eliane O.
;
Dias, Herbert J.
;
Oliveira, Anderson R. M.
;
Crotti, Antonio E. M.
Número total de Autores: 4
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Química Nova; v. 48, n. 6, p. 5-pg., 2025-01-01. |
| Resumo | |
Chemoenzymatic strategies to synthesize complex molecules have been developed by combining biocatalytic and synthetic methods in a multistep approach toward a target molecule. Dihydrobenzofuran neolignans (DBNs), a class of plant-derived natural compounds, display several biological activities. Oxidative coupling of phenylpropanoids is commonly used to obtain DBNs, but yields are low, and stereochemical control is poor. This study reports the novel eco-friendly and stereoselective conversion of methyl trans-ferulate (1) into DBN 2 ((+/-)-trans-dehydrodiferulate dimethyl ester) promoted by Trametes versicolor FC in 47% yield. Compared to Ag2O-promoted oxidative coupling, this biotransformation approach is enantioselective (66.7% ee of the main enantiomer) and affords DBN 2, as confirmed by chiral-HPLC (high-performance liquid chromatography) and NMR (nuclear magnetic resonance) data analyses. Our preliminary results highlighted the combination of biotransformation and traditional chemical processes as a promising starting point for obtaining DBNs from the corresponding phenylpropanoids enantioselectively. (AU) | |
| Processo FAPESP: | 21/10098-4 - Avaliação enantiosseletiva in vitro do efeito de praguicidas quirais sobre as principais enzimas do citocromo P450 de humanos envolvidas no metabolismo de fármacos: correlação in vitro-in vivo e predição de interação praguicida-fármaco |
| Beneficiário: | Anderson Rodrigo Moraes de Oliveira |
| Modalidade de apoio: | Auxílio à Pesquisa - Regular |
| Processo FAPESP: | 13/20094-0 - Avaliação da atividade antiparasitária e inseticida de compostos benzofurânicos e estudo de suas reações de fragmentação em fase gasosa empregando espectrometria de massas sequencial |
| Beneficiário: | Antônio Eduardo Miller Crotti |
| Modalidade de apoio: | Auxílio à Pesquisa - Regular |