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

Renata Studzińska,Renata Kołodziejska,Aleksandra Karczmarska-Wódzka,Hanna Pawluk,Alina Woźniak

doi:10.3390/catal8070290

Renata Studzińska, Renata Kołodziejska + Show 3 more

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https://doi.org/10.3390/catal8070290

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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.

Highlights

Biotransformation, i.e., enzyme-catalyzed reactions, have been used over millions of years in nature to carry out reactions that are complicated from a chemical point of view
Dehydrogenases in living organisms catalyze the reaction of the oxidation of alcohols to carbonyl compounds by mediating the transfer of a hydride ion from the cofactor on the substrate
Work, we we present present the the microbial microbialbiotransformation biotransformationofofthe the1-substituted-5-methyl-3-(2-oxo-21-substituted-5-methyl-3-(2-oxophenylethyl)pyrimidine-2,4(1H,3H)-dione

Summary

Introduction

Biotransformation, i.e., enzyme-catalyzed reactions, have been used over millions of years in nature to carry out reactions that are complicated from a chemical point of view. Biotransformations catalyzed by isolated enzymes and by whole cells of microorganisms, in terms of microorganisms growing or resting cells, are employed for the synthesis of chemicals such as pharmaceuticals, agrochemicals, and natural products [1,2,3]. Dehydrogenases in living organisms catalyze the reaction of the oxidation of alcohols to carbonyl compounds by mediating the transfer of a hydride ion from the cofactor on the substrate. They have the ability to catalyze a reverse reaction in a reduction reaction. Dehydrogenases transfer the hydride ion (pro-S or pro-R) from the cofactor to one of the prochiral

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