Highly active and recyclable immobilized multiple enzymes for one-pot enantioselective cascade reactions: Synthesis of (R)- and (S)--amino acids from racemic -hydroxy acids
APPLIED CATALYSIS B-ENVIRONMENT AND ENERGY(2024)
摘要
Cascade biotransformation of racemic alcohols to enantiopure amines is highly wanted in pharmaceutical manufacturing but requires green and efficient solution. Here we developed the first immobilized enzyme-based approach for this transformation, being cleaner and more productive than whole-cells biocatalysis, and more economic and higher-yielding than using isolated enzymes. As demonstration, the conversion of racemic mandelic acids to high-value (R)- or (S)-phenylglycines was achieved by immobilized enantioselective alcohol oxidase, racemase, catalase, and (S)- or (R)-transaminase. Co-immobilization of the four enzymes on Ni-NTA functionalised carriers gave high enzyme loadings (192-195 mg enzyme/g carrier), loading efficiencies (97-98%), and free enzyme activities (107-113%). Immobilized enzymes transformed racemic mandelic acids to the corresponding four (S)-phenylglycines in 91-99% ee and 82-95% yields or five (R)-phenylglycines in 93-99% ee and 83-94% yields. These catalysts showed good recyclability, retaining 86-98% productivities in the fifth reaction cycles.
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关键词
Cascade reaction,Green synthesis,Immobilized enzymes,Phenylglyoxylic acid,(R)-and(S)-phenylglycine
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