A collaborative research effort between the School of Life Sciences, University of Hyderabad, and IIIT Hyderabad has led to a significant breakthrough in biocatalytic asymmetric synthesis. The study, published in ACS Catalysis, demonstrates the discovery of a native enzyme, Baliospermum montanum hydroxynitrile lyase (BmHNL), exhibiting complementary diastereoselectivity in asymmetric Henry reaction. ACS Catalysis is a prestigious journal of the American Chemical Society with an impact factor of 11.7. Read more at: https://doi.org/10.1021/acscatal.5c01752

 

Prof. Santosh Kumar Padhi, and his Ph.D. student Ayon Chatterjee, Department of Biochemistry, School of Life Sciences, University of Hyderabad in collaboration with Professor U. Deva Priyakumar and his Ph.D. student Pradeep Kumar Pal, of IIIT, Hyderabad have carried out this research.

Key Findings

– Diastereocomplementary Synthesis: BmHNL catalyzes the production of both anti- and syn-β-nitroalcohols with high stereoselectivity, yielding products with up to >99% conversion, >99% ee, and >99% de.

– Reusability: BmHNL can be reused for 20 cycles in the synthesis of (1S,2R)-2-nitro-1-phenylpropan-1-ol (NPP), demonstrating its potential for industrial applications.

– Scaled-up Synthesis: BmHNL was successfully employed in the synthesis of (1S,2R)-NPP and (1S,2S)-NPP, a precursor to D-norpseudoephedrine.

– Mechanistic Studies: Isotope labeling and density functional theory-based computational studies provided insights into the origin of inverse diastereoselectivity.

 

Implications

This study showcases the potential of biocatalyst in greener technology and stereo controlled production of diverse β-nitroalcohols. The discovery of BmHNL as a specialized biocatalyst opens up new avenues for industrial applications, with a patent filed for this technology. The study highlights the growing importance of enzymes as catalysts in biomanufacturing and the potential of biocatalysts to revolutionize chemical synthesis.

 

For any further details please contact Dr. Santosh Kumar Padhiskpadhi@uohyd.ac.in