Plant-Mediated Enantioselective Transformation of Indan-1-one and Indan-1-ol. Part 2.

Mączka Mączka,Galek Galek,Grabarczyk Grabarczyk,Wińska Wińska

doi:10.3390/molecules24234342

Mączka Mączka, Galek Galek + Show 2 more

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https://doi.org/10.3390/molecules24234342

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Abstract

The main purpose of this publication was to obtain the S-enantiomer of indan-1-ol with high enantiomeric excess and satisfactory yield. In our research, we used carrot callus cultures (Daucus carota L.), whereby the enzymatic system reduced indan-1-one and oxidized indan-1-ol. During the reaction of reduction, after five days, we received over 50% conversion, with the enantiomeric excess of the formed S-alcohol above 99%. In turn, during the oxidation of racemic indan-1-ol after 15 days, 36.7% of alcohol with an enantiomeric excess 57.4% S(+) remained in the reaction mixture. In addition, our research confirmed that the reactions of reduction and oxidation are competing reactions during the transformation of indan-1-ol and indan-1-one in carrot callus cultures.

Highlights

Indan-1-ol is example of secondary alcohol, which was observed as a semi-volatile product ofLemna sp. [1] and is a component (8%) of floral essential oil of Guettarda poasana (Rubiaceae) [2]
Analog of indanol: (1S, 2R)-1-amino-2-indanol is a key intermediate in the synthesis of Indinavir (Crixivan® ), which acts as an HIV protease inhibitor in antiretroviral therapy
In our research we have proved that the carrot cell cultures obtained by us are able to carry out both reactions: oxidation of indan-1-ol and reduction of indan-1-one

Summary

Introduction

Indan-1-ol is example of secondary alcohol, which was observed as a semi-volatile product ofLemna sp. [1] and is a component (8%) of floral essential oil of Guettarda poasana (Rubiaceae) [2]. The derivative of indanol, which was isolated from culture of Ganoderma applanatum, suppressed the growth of Fusobacterium nucleatum – a prominent member of the oral microflora implicated in periodontitis [3]. Analog of indanol: (1S, 2R)-1-amino-2-indanol is a key intermediate in the synthesis of Indinavir (Crixivan® ), which acts as an HIV protease inhibitor in antiretroviral therapy. It contains five chiral centers with 32 possible stereoisomers, only a single stereoconformation of Indinavir confers the desired therapeutic effect [4,5]. Indatraline, an analog of indanol, is used in the treatment of cocaine addiction [7]. PT285 and PT2877 are second-generation inhibitors of the hypoxia-inducible factor 2α (HIF-2α), key oncogenic driver in renal carcinoma [8]

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