Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2
| العنوان: | Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2 |
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| المؤلفون: | Engin Şahin, Yasemin Baydaş, Erbay Kalay |
| المصدر: | Chemical Papers. 75:1147-1155 |
| بيانات النشر: | Springer Science and Business Media LLC, 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | Lactobacillus kefiri, Benziodarone, Ethanol, General Chemical Engineering, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Biochemistry, Industrial and Manufacturing Engineering, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Biocatalysis, Yield (chemistry), Materials Chemistry, medicine, Organic chemistry, Coronary vasodilator, 0210 nano-technology, Enantiomeric excess, medicine.drug |
| الوصف: | Chiral heterocyclic secondary alcohols have received much attention due to their widespread use in pharmaceutical intermediates. In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asymmetric reduction of prochiral ketones to chiral secondary alcohols. Secondary chiral carbinols were obtained by asymmetric bioreduction of different prochiral substrates with results up to > 99% enantiomeric excess (ee). (R)-1-(benzofuran-2-yl)ethanol 5a, which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective β-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70 g of (R)-5a in enantiomerically pure form was obtained in 96% yield. Also, production of (R)-5a in terms of yield and gram scale through catalytic asymmetric reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcohols compared to chemical processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis. |
| تدمد: | 1336-9075 2585-7290 |
| DOI: | 10.1007/s11696-020-01364-2 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::ae68caf5c7f5c566887a287070b8c1ea https://doi.org/10.1007/s11696-020-01364-2 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........ae68caf5c7f5c566887a287070b8c1ea |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 13369075 25857290 |
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| DOI: | 10.1007/s11696-020-01364-2 |