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Reconstruction of Hyper‐Thermostable Ancestral L‐Amino Acid Oxidase to Perform Deracemization to D‐Amino Acids

Chiharu Ishida, Ryo Miyata, Fumihito Hasebe, Azusa Miyata, Shigenori Kumazawa, Sohei Ito, Shogo Nakano

2021ChemCatChem26 citationsDOI

Abstract

Abstract L‐amino acid oxidases (LAAOs) with broad substrate specificity can be used in the deracemization of D,L‐amino acids (D,L‐AAs) to their D‐enantiomers. Hyper‐thermostable LAAO (HTAncLAAO) was designed through a combination of manual sequence data mining and ancestral sequence reconstruction. Soluble expression of HTAncLAAO (>50 mg/L) can be achieved using an E. coli system. HTAncLAAO, which recognizes seven L‐AAs as substrates, exhibits extremely high thermal stability and long‐term stability; the t 1/2 value was 95 °C and <5% activity loss after incubation of the enzyme at 30 °C for 1 week. Deracemization could be achieved at 40 °C with a small amount of enzymes compared to previously reported LAAOs. A total of 0.4 mg (2 U) of HTAncLAAO is enough to deracemize three D,L‐AAs at a preparative scale with high enantiomeric excess (>99 % ee , D‐enantiomer). These results suggest that HTAncLAAO is an excellent biocatalyst to perform this deracemization.

Topics & Concepts

EnantiomerBiocatalysisAmino acidThermal stabilityEnzymeEnantiomeric excessOxidase testD-amino acid oxidaseChemistrySubstrate (aquarium)StereochemistryBiochemistryEnantioselective synthesisBiologyOrganic chemistryReaction mechanismCatalysisEcologyAmino Acid Enzymes and MetabolismPolyamine Metabolism and ApplicationsEnzyme Structure and Function