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Catalysts 2018, 8(2), 55; doi:10.3390/catal8020055

Whole-Cell Biocatalyst for Chemoenzymatic Total Synthesis of Rivastigmine

1
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari «Aldo Moro», Via E. Orabona 4, I-70125 Bari, Italy
2
Consorzio C.I.N.M.P.I.S., Dipartimento di Farmacia-Scienze del Farmaco, Via E. Orabona 4, I-70125 Bari, Italy
3
Dipartimento di Bioscienze, Biotecnologie e Biofarmaceutica, Università degli Studi di Bari «Aldo Moro», Via E. Orabona 4, I-70125 Bari, Italy
4
Consorzio CIRCC, Via Celso Ulpiani 27, I-70126 Bari, Italy
*
Authors to whom correspondence should be addressed.
Received: 16 January 2018 / Revised: 26 January 2018 / Accepted: 29 January 2018 / Published: 31 January 2018
(This article belongs to the Special Issue Chiral Building Blocks via Asymmetric Catalysis)
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Abstract

Biocatalytic processes are increasingly playing a key role in the development of sustainable asymmetric syntheses, which are central to pharmaceutical companies for the production of chiral enantiopure drugs. This work describes a simple and economically viable chemoenzymatic process for the production of (S)-rivastigmine, which is an important drug for the treatment of mild to moderate dementia of the Alzheimer’s type. The described protocol involves the R-regioselective bioreduction of an aromatic ketone by Lactobacillus reuteri DSM 20016 whole cells in phosphate buffered saline (PBS) (37 °C, 24 h) as a key step. Biocatalytic performance of baker’s yeast whole cells in water and in aqueous eutectic mixtures have been evaluated and discussed as well. The route is scalable, environmentally friendly, and the target drug is obtained via four steps in overall 78% yield and 98% ee. View Full-Text
Keywords: rivastigmine; chemoenzymatic synthesis; bioreduction; whole-cell biocatalyst; (R)-arylethanols; baker’s yeast; deep eutectic solvents rivastigmine; chemoenzymatic synthesis; bioreduction; whole-cell biocatalyst; (R)-arylethanols; baker’s yeast; deep eutectic solvents
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Vitale, P.; Perna, F.M.; Agrimi, G.; Pisano, I.; Mirizzi, F.; Capobianco, R.V.; Capriati, V. Whole-Cell Biocatalyst for Chemoenzymatic Total Synthesis of Rivastigmine. Catalysts 2018, 8, 55.

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