Work

STEREOSELECTIVE OXIDATIVE COUPLING OF METHYL TRANS-FERULATE TO (±)-TRANS-DEHYDRODIFERULATE DIMETHYL ESTER BY Trametes versicolor FC: AN ENANTIOSELECTIVE GREEN APPROACH

Year: 2025

Type: article

Abstract: Chemoenzymatic strategies for synthesizing complex molecules have been raised by combining biocatalytic and synthetic methods in a multistep approach toward a target molecule. Dihydrobenzofuran neolignans (DBNs) are a class of plant-derived natural compounds that display several biological activities. They are commonly obtained in low yields and without stereochemistry control through the oxidative coupling of phenylpropanoids. This study reports the novel eco-friendly, and regio- and diastereoselective conversion of methyl trans-ferulate (1) into DBN 2 ((±)-trans-dehydrodiferulate dimethyl ester) promoted by Trametes versicolor FC. The biotransformation approach afforded DBN 2 in 47% yield, with an interesting enantioselectivity compared to Ag2O-promoted oxidative coupling, as confirmed by chiral-HPLC analyses.

Source: Química Nova

DOI: 10.21577/0100-4042.20250147

Authors: Eliane O. Silva, Herbert J. Dias, Anderson R. M. Oliveira, Antônio E. M. Crotti

Language: English

Topic: Plant-derived Lignans Synthesis and Bioactivity

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: gold

Estimated APC paid: $330

Funders: Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico