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Engineering of Cascade Reactions and Alditol Oxidase for High‐Yielding Synthesis of (R)‐Phenylethanolamine from Styrene, l‐Phenylalanine, Glycerol or Glucose

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Biotransformations: Novel 4- and 6-enzyme cascades were developed for one-pot synthesis of (R)-PEA with high ee and high yield from styrene and l-phenylalanine, respectively. The limiting enzyme in the cascade, AldO, was successfully engineered to enhance activity. Coupling of l-Phe biosynthesis pathway with 6-enzyme cascade achieved synthesis of (R)-PEA from glycerol or glucose, respectively.


Abstract

(R)-phenylethanolamine (PEA) is a useful and valuable chiral chemical and requires enantioselective and efficient synthesis method. A novel SMO-StEH-AldO-CvTA-catalyzed cascade reaction was established to convert styrene to (R)-PEA via epoxidation-hydrolysis-oxidation-amination. The key transformation of (R)-1-phenyl-1,2-ethanediol to (R)-PEA in the cascade was achieved in 94 % conversion via AldO-CvTA. The limiting enzyme AldO was engineered through directed evolution, yielding a mutant AldO(MVIK) with 3-fold enhanced catalytic efficiency. The use of AldO(MVIK) in the 4-enzyme cascade significantly increased the productivity than the use of AldO, yielding 34.6 mM (R)-PEA with >99 % ee. By incorporating deamination and decarboxylation enzymes, a 6-enzyme cascade was engineered to produce 23.7 mM (R)-PEA from l-phenylalanine. Coupling of l-phenylalanine biosynthesis pathway with 6-enzyme cascade enabled synthesis of (R)-PEA from glycerol or glucose, producing 6.8 mM and 6.5 mM (R)-PEA, respectively. The developed cascade biotransformations provide direct synthesis of (R)-PEA from either simple chemicals or renewable feedstocks.

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