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Open AccessArticle

Enantioselective Bioreduction of Prochiral Pyrimidine Base Derivatives by Boni Protect Fungicide Containing Live Cells of Aureobasidium pullulans

1
Department of Medical Biology and Biochemistry, Faculty of Medicine, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toruń, Karłowicza 24, 85–092 Bydgoszcz, Poland
2
Department of Organic Chemistry, Faculty of Pharmacy, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toruń, Jurasza 2, 85–089 Bydgoszcz, Poland
3
Department of Pharmacology and Therapy, Faculty of Medicine, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toruń, M. Curie Skłodowskiej 9, 85–094 Bydgoszcz, Poland
*
Author to whom correspondence should be addressed.
Catalysts 2018, 8(7), 290; https://doi.org/10.3390/catal8070290
Received: 22 June 2018 / Revised: 11 July 2018 / Accepted: 16 July 2018 / Published: 18 July 2018
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Abstract

The enzymatic enantioselective bioreduction of prochiral 1-substituted-5-methyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-diones to corresponding chiral alcohols by Boni Protect fungicide containing live cells of Aureobasidium pullulans was studied. The microbe-catalyzed reduction of bulky-bulky ketones provides enantiomerically pure products (96–99% ee). In the presence of A. pullulans (Aureobasidium pullulans), one of the enantiotopic hydrides of the dihydropyridine ring coenzyme is selectively transferred to the si sides of the prochiral carbonyl group to give secondary alcohols with R configuration. The reactions were performed under various conditions in order to optimize the procedure with respect to time, solvent, and temperature. The present methodology demonstrates an alternative green way for the synthesis of chiral alcohols in a simple, economical, and eco-friendly biotransformation. View Full-Text
Keywords: biotransformation microbe-catalyzed reduction; prochiral ketones; stereochemistry; antifungal agent; Aureobasidium pullulans biotransformation microbe-catalyzed reduction; prochiral ketones; stereochemistry; antifungal agent; Aureobasidium pullulans
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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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Kołodziejska, R.; Studzińska, R.; Pawluk, H.; Karczmarska-Wódzka, A.; Woźniak, A. Enantioselective Bioreduction of Prochiral Pyrimidine Base Derivatives by Boni Protect Fungicide Containing Live Cells of Aureobasidium pullulans. Catalysts 2018, 8, 290.

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