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Development of an Enzyme Cascade System for the Synthesis of Enantiomerically Pure D-Amino Acids Utilizing Ancestral L-Amino Acid Oxidase.
Araseki, Hayato; Sugishima, Narumi; Chisuga, Taichi; Nakano, Shogo.
Afiliação
  • Araseki H; Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan for S.N.
  • Sugishima N; Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan for S.N.
  • Chisuga T; Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan for S.N.
  • Nakano S; Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan for S.N.
Chembiochem ; 25(8): e202400036, 2024 Apr 16.
Article em En | MEDLINE | ID: mdl-38385659
ABSTRACT
Enantiomerically pure D-amino acids hold significant potential as precursors for synthesizing various fine chemicals, including peptide-based drugs and other pharmaceuticals. This study focuses on establishing an enzymatic cascade system capable of converting various L-amino acids into their D-isomers. The system integrates four enzymes ancestral L-amino acid oxidase (AncLAAO-N4), D-amino acid dehydrogenase (DAADH), D-glucose dehydrogenase (GDH), and catalase. AncLAAO-N4 initiates the process by converting L-amino acids to corresponding keto acids, which are then stereo-selectively aminated to D-amino acids by DAADH using NADPH and NH4Cl. Concurrently, any generated H2O2 is decomposed into O2 and H2O by catalase, while GDH regenerates NADPH from D-glucose. Optimization of reaction conditions and substrate concentrations enabled the successful synthesis of five D-amino acids, including a D-Phe derivative, three D-Trp derivatives, and D-phenylglycine, all with high enantiopurity (>99 % ee) at a preparative scale (>100 mg). This system demonstrates a versatile approach for producing a diverse array of D-amino acids.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: L-Aminoácido Oxidase / Aminoácidos Idioma: En Revista: Chembiochem Assunto da revista: BIOQUIMICA Ano de publicação: 2024 Tipo de documento: Article País de publicação: Alemanha

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: L-Aminoácido Oxidase / Aminoácidos Idioma: En Revista: Chembiochem Assunto da revista: BIOQUIMICA Ano de publicação: 2024 Tipo de documento: Article País de publicação: Alemanha