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Rhizopus arrhizus mediated SAR studies in chemoselective biotransformation of haloketones at ambient temperature
Biocatalysis and Biotransformation ( IF 1.8 ) Pub Date : 2021-09-07 , DOI: 10.1080/10242422.2021.1974006
Prabha R. Salokhe 1 , Rajeshri S. Salunkhe 2
Affiliation  

Abstract

We have demonstrated a green chemistry approach using the fungus Rhizopus arrhizus for the reductive dehalogenation and synthesis of chiral secondary carbinols and halohydrins of pharmaceutical importance in mild, inexpensive, and environmental friendly process at ambient temperature. In the present study, we have succeeded in unravelling the relationship between the position of the substituent group in the structure of substrate and bioreduction activity of the fungus Rhizopus arrhizus. The asymmetric reduction of the carbonyl group to corresponding chiral halohydrin takes place with good yield and excellent enantiomeric excess (≥92%) when the substituent halogen is on the aromatic nucleus. However, novel results concerning reductive dehalogenation are obtained when halogen is incorporated in the alkyl side chain. Thus, the fungus Rhizopus arrhizus has great potential to bring chemoenzymatic biotransformation of halo ketones. Various influential processing parameters such as microbe selection, temperature, pH, etc. were also investigated to optimize the growth of biocatalyst.



中文翻译:

根根霉介导的 SAR 研究在环境温度下卤酮的化学选择性生物转化

摘要

我们已经展示了一种绿色化学方法,该方法使用真菌根霉在环境温度下以温和、廉价和环保的工艺进行还原脱卤和合成具有药学重要性的手性仲醇和卤代醇。在本研究中,我们成功地阐明了取代基在底物结构中的位置与真菌根根霉的生物还原活性之间的关系。. 当取代基卤素在芳核上时,羰基不对称还原为相应的手性卤代醇,产率高,对映体过量(≥92%)也很好。然而,当卤素结合到烷基侧链中时,获得了关于还原脱卤的新结果。因此,真菌根霉具有巨大的潜力,可以带来卤代酮的化学酶生物转化。还研究了各种有影响的工艺参数,例如微生物选择、温度、pH 等,以优化生物催化剂的生长。

更新日期:2021-09-07
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