Abstract
The main purpose of this work was to discover the way to obtain pure enantiomers of indan-1-ol. The subject of the study was the ability of the plant enzyme system to reduce the carbonyl group of indan-1-one, as well as to oxidize the hydroxyl group of racemic indan-1-ol. Locally available fruit and vegetables were selected for stereoselective biotransformation. During the reduction, mainly alcohol of the S-(+)-configuration with a high enantiomeric excess (ee = 99%) was obtained. The opposite enantiomer was obtained in bioreduction with the apple and parsley. Racemic indan-1-ol was oxidized by all catalysts. The best result was obtained for the Jerusalem artichoke: Over 50% conversion was observed after 1 h, and the enantiomeric excess of unreacted R-(–)-indan1-ol was 100%.
Highlights
In the last decade the need to obtain applicable biologically-active enantiopure compounds has been growing increasingly, because the way they act within living organisms depends largely on their absolute configuration
Table thethe indan-1-one plant biotransformations determined by GC
We carried out biotransformation using plant catalysts to obtain indanol isomers with a high enantiomeric excess
Summary
In the last decade the need to obtain applicable biologically-active enantiopure compounds has been growing increasingly, because the way they act within living organisms depends largely on their absolute configuration. Chiral secondary alcohols are increasingly recognized as valuable chiral building blocks in the organic syntheses of pharmaceuticals and agrochemicals In the past, they were produced by several methods, such as by the use of chiral ligands [2,3], separation by chiral chromatography [4] and the application of chiral metal complexes in the asymmetric reduction of prochiral compounds [5]. They were produced by several methods, such as by the use of chiral ligands [2,3], separation by chiral chromatography [4] and the application of chiral metal complexes in the asymmetric reduction of prochiral compounds [5] All of these processes have their own inherent drawbacks, including difficulty in operation, generation of by-products, exorbitant cost and harmful effects upon the environment [6]. This problem can be solved by biocatalysis, which can additively shorten the synthetic route and enable the achievement of high yields with excellent chemo-, regio- and stereo-selectivity [7]
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