3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxindole precursor by classical metal-catalysed chemical reductions of the olefin. In this work we present a biocatalytic approach for the reduction of oxindole-based olefins using baker's yeast. All the substrates were efficiently reduced in high yields. When an α,β-unsaturated ketone was used, the corresponding saturated alcohol was obtained in high yield and ee. To further investigate the enzyme-substrate interactions a molecular docking study was also performed.
Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast / A. Rossetti, A. Sacchetti, M. Bonfanti, G. Roda, G. Rainoldi, A. Silvani. - In: TETRAHEDRON. - ISSN 0040-4020. - 73:31(2017), pp. 4584-4590.
|Titolo:||Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast|
|Parole Chiave:||Baker's yeast; Biocatalysis; Molecular docking; Oxindole; Reduction; Biochemistry; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||2017|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.tet.2017.06.022|
|Appare nelle tipologie:||01 - Articolo su periodico|