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.
Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
G. Roda;G. Rainoldi;A. Silvani
2017
Abstract
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.File | Dimensione | Formato | |
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