What is it about?

asymmetric reduction, biocatalyst, biotransformations, piperonyl carbinol, piperonyl ring

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Why is it important?

we report the asymmetric reduction of piperonyl methyl ketone 1 to the (R)‐1‐(1,3‐benzodioxol‐ 5‐yl)ethanol 2 by L paracasei BD101 with >99% ee and 89% yields. Moreover, to the best of our knowledge, this is the first report on asymmetric reduction of piperonyl methyl ketone using biocatalyst.

Perspectives

In summary, screening of 15 bacterial strains has been performed for the reduction of 1‐(benzo[d][1,3]dioxol‐5‐yl)ethanone (1). Among the whole cell bacteria used for the reduction of 1, L paracasei BD101 was found to be the best biocatalyst. Important parameters such as pH, temperature, incubation time, and agitation speed were optimized for maximum product yield with excellent enantioselectivity. (R)‐1‐(1,3‐benzodioxol‐5‐yl)ethanol (2) with high enantiomeric purity was produced in gram scale with both excellent ee (>99%) and yield (89%), through a cheap, simple, and efficient process. Importantly, this is the first report on the gram‐scale production of 2 with L paracasei BD101 as a biocatalyst. This strain shows promise as a highly attractive candidate for the biocatalytic preparation of other carbinols in future studies. This is efficient and eco‐friendly system that exhibits excellent enantioselectivity and can be applied for the synthesis of valuable enantiopure secondary alcohols, which can be important intermediate product for the synthesis of drugs and biologically active compound.

Engin şahİn
Bayburt Universitesi

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This page is a summary of: Production of (R )-1-(1,3-benzodioxol-5-yl)ethanol in high enantiomeric purity by Lactobacillus paracasei BD101, Chirality, November 2017, Wiley,
DOI: 10.1002/chir.22782.
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