New biocatalytic route for the production of enantioenriched β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils
| Autor: | Francisco Javier Las Heras-Vázquez, Sergio Martínez-Rodríguez, Ana Isabel Martínez-Gómez, Liisa T. Kanerva, Josefa María Clemente-Jiménez, Felipe Rodríguez-Vico, Xiang-Guo Li |
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| Rok vydání: | 2012 |
| Předmět: |
Alanine
Amidohydrolase biology Stereochemistry Enantioselective synthesis Dihydrouracil Bioengineering Agrobacterium tumefaciens ta3111 biology.organism_classification Applied Microbiology and Biotechnology Biochemistry Kinetic resolution chemistry.chemical_compound chemistry Biocatalysis Dihydropyrimidinase |
| Zdroj: | Process Biochemistry. 47:2090-2096 |
| ISSN: | 1359-5113 |
| DOI: | 10.1016/j.procbio.2012.07.026 |
| Popis: | Taking advantage of the catalytic promiscuity of pyrimidine-catabolism enzymes (dihydropyrimidinase (E.C. 3.5.2.2), N -carbamoyl-β-alanine amidohydrolase (E.C. 3.5.1.6)), the production of different β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils has been evaluated using a mimesis approach. In this work, the S -enantioselective character of dihydropyrimidinase from Sinorizhobium meliloti toward 6-monosubstituted dihydrouracil derivatives has been shown. An inverted R -/ S -enantioselectivity of N -carbamoyl-β-alanine amidohydrolase from Agrobacterium tumefaciens toward two different N -carbamoyl-β-amino acids has been proved. Our results have shown for the first time that this mimetic tandem constitutes an interesting biotechnological tool for the preparation of different β-alanine derivatives in an environmentally friendly way, allowing the production of enantioenriched ( R )-α-phenyl-β-alanine (e.e. > 95%) and ( R )-α-methyl-β-alanine (e.e. > 90%). |
| Databáze: | OpenAIRE |
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