Immobilized Arabidopsis thaliana Hydroxynitrile Lyase-Catalyzed Retro-Henry Reaction in the Synthesis of (S)-β-Nitroalcohols

Enantiopure β-nitroalcohols are versatile intermediates used in the synthesis of important pharmaceuticals and chiral synthons. In this article, immobilized Arabidopsis thaliana HNL ( At HNL)-catalyzed preparation of ( S )-β-nitroalcohols from their racemic mixtures via retro-Henry reaction was stud...

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Bibliographic Details
Published in:Applied biochemistry and biotechnology 2021-02, Vol.193 (2), p.560-576
Main Authors: Rao, D. H. Sreenivasa, Shivani, Kummari, Padhi, Santosh Kumar
Format: Article
Language:English
Subjects:
Arabidopsis thaliana
Biochemistry
Biotechnology
Catalysis
Catalysts
Chemical synthesis
Chemistry
Chemistry and Materials Science
Conversion
Diatomaceous earth
Enzymes
Immobilization
Intermediates
pH effects
Selectivity
Stability
Substrates
Tricalcium aluminate
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Summary:Enantiopure β-nitroalcohols are versatile intermediates used in the synthesis of important pharmaceuticals and chiral synthons. In this article, immobilized Arabidopsis thaliana HNL ( At HNL)-catalyzed preparation of ( S )-β-nitroalcohols from their racemic mixtures via retro-Henry reaction was studied. At HNL used in biocatalysis was immobilized by physical adsorption in inexpensive celite®545. Under optimized biocatalytic conditions, the total turnover number of the catalyst has improved 2.3-fold for ( S )-2-nitro-1-phenylethanol (NPE) synthesis, than free enzyme catalysis. This study reported for the first time celite- At HNL–catalyzed retro-Henry reaction at low pH. At pH 4.5 and 5.0, 62% ee and 41% conversion, and 97% ee and 42% conversion of ( S )-NPE were obtained respectively, while the free enzyme inactivates at pH
ISSN:0273-2289
1559-0291
DOI:10.1007/s12010-020-03442-3