Asymmetric synthesis of nonproteinogenic amino acids with l-amino acid transaminase: synthesis of (2S)-2-amino-4-oxo-4-phenylbutyric and (3E,2S)-2-amino-4-phenylbutenoic acids |
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| Affiliation: | 1. UMYMFOR – Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3° Piso, (1428) Buenos Aires, Argentina;2. Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP2000, Rosario, Argentina;1. Dipartimento di Scienze Chimiche e Geologiche, Università di Cagliari, Cittadella Universitaria, I-09042 Monserrato-Cagliari, Italy;2. Dipartimento di Chimica, University of Pavia, Pavia, Italy;3. Faculty of Natural and Environmental Sciences, University of Southampton, Southampton, United Kingdom;1. Department of Biochemistry and Molecular Biology, University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA;2. Department of Chemistry, University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA;1. Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy;2. CIRCMSB (Consorzio Interuniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici), Parma Unit, University of Parma, Italy;3. Dipartimento di Scienze degli Alimenti e del Farmaco, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy;4. Dipartimento di Chimica e Farmacia, Università di Sassari, Via Vienna 2, I-07100 Sassari, Italy;5. Rega Institute for Medical Research, KU Leuven – University of Leuven, B-3000 Leuven, Belgium;1. Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan;2. South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan;3. Advanced Research Support Center (ADRES), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan |
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| Abstract: | 2,4-Dioxo-4-phenylbutyric acid and 2-oxo-4-phenylbut-3-enoic acid are converted to the corresponding (S)-2-amino acids by recombinant Escherichia coli whole cells over-expressing aromatic transaminase from Enterobacter sp. BK2K-1 (AroATEs) in high yields (68–78%) and high enantiomeric purity (>99%) using l-aspartic acid as an amino donor. |
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