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Application L2202

Asymmetric hydrogenation of C = C bonds in a SpinChem reactor by immobilized old yellow enzyme and glucose dehydrogenase

Teng Ma, Weixi Kong, Yunting Liu, Hao Zhao, Yaping Ouyang, Jing Gao, Liya Zhou, and Yanjun Jiang

Appl. Biochem. Biotechnol., 2022, 194, pp. 4999–5016.

"The application of immobilized enzymes in pharmaceutical and bulk chemical production has been shown to be economically viable. We demonstrate the exceptional performance of a method that immobilizes the old yellow enzyme YqjM and glucose dehydrogenase (GDH) on resin for the asymmetric hydrogenation (AH) of C = C bonds in a SpinChem reactor. When immobilized YqjM and GDH are reused 10 times, the conversion of 2-methylcyclopentenone could reach 78%. Which is because the rotor of the SpinChem reactor effectively reduces catalyst damage caused by shear force in the reaction system. When the substrate concentration is 175 mM, an 87% conversion of 2-methylcyclopentenone is obtained. The method is also observed to perform well for the AH of C = C bonds in other unsaturated carbonyl compounds with the SpinChem reactor. Thus, this method has great potential for application in the enzymatic production of chiral compounds."

Conversion and ee shown versus number of recycles for the enzymes non-immobilized, immobilized on separate resins, and co-immobilized.

Highlights:

  • ”[…] the SpinChem reactor effectively reduces catalyst damage […]”
  • ”[…] using immobilized enzymes in the SpinChem reactor can be conducted with operational ease and recycled multiple times while demonstrating improved stability; thus, this technology has become increasingly appealing to users in the biocatalytic field.”