Enzymatic synthesis of cyclic amino acids by N-methyl-l-amino acid dehydrogenase from Pseudomonas putida |
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| Institution: | 1. Mitsubishi Chemical Group, Science and Technology Research Center Inc., 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-8502, Japan;2. Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan;3. Department of Biological Science, Graduate School of Science, Osaka University, Suita, Osaka 565-0871, Japan;1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary;2. Fermentia Microbiological Ltd., Berlini út 47-49, Budapest, H-1045, Hungary;3. Department of Applied Biotechnology and Food Science, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary;4. Institute of Enzymology, Research Center for Natural Sciences, Hungarian Academy of Science, H-1117 Budapest, Hungary;5. KTH Royal Institute of Technology, Division of Industrial Biotechnology, School of Biotechnology, AlbaNova University Center, SE-106 91 Stockholm, Sweden;6. Biocatalysis and Biotransformation Research Centre, Faculty of Chemistry and Chemical Engineering, Babeș-Bolyai University of Cluj-Napoca, Arany János Str. 11, RO-400028 Cluj-Napoca, Romania;7. SynBiocat Ltd., Szilasliget u 3, Budapest, H-1172, Hungary;1. acib—Austrian Centre of Industrial Biotechnology, Petersgasse 14, A-8010 Graz, Austria;2. Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, A‐8010 Graz, Austria;3. Department of Organic Chemistry, Graz University of Technology, Stremayrgasse 9/4, A‐8010 Graz, Austria;4. Department of Biotechnology, University of Natural Resources and Life Sciences, and Department of Biotechnology, Muthgasse 18, A-1190 Vienna, Austria;5. enGenes Biotech GmbH, Mooslackengasse 17, A-1190 Vienna, Austria |
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| Abstract: | A new enzymatic system for the synthesis of enantiomerically pure cyclic amino acids (CAA) from the corresponding diamino acids or racemic CAA is described. α,ω-Diamino acids were oxidized to α-keto acids with amino acid oxidases (AAO). The α-keto acids were spontaneously transformed into cyclic imino acids in the reaction medium. The resulting imines were reduced to the l-form CAA with N-methyl-l-amino acid dehydrogenase (NMAADH) from Pseudomonas putida ATCC12633 using NADPH as a cofactor. l-Form CAA were also obtained from racemic CAA using d-amino-acid oxidase and NMAADH. Using this method, a new compound 1,4]-thiazepane-3-carboxylic acid (Fig. 1) was synthesized from aminopropylcystein. |
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