Mechanism-inspired engineering of phenylalanine aminomutase for enhanced β-regioselective asymmetric amination of cinnamates
| Autor: | Bian Wu, Dick B. Janssen, Ben L. Feringa, Gjalt G. Wybenga, Gerrit J. Poelarends, Sebastian Bartsch, Matthew M. Heberling, Bauke W. Dijkstra, Wiktor Szymanski, Stefaan Marie André De Wildeman |
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| Přispěvatelé: | Groningen Biomolecular Sciences and Biotechnology, Biotechnology, Stratingh Institute of Chemistry, X-ray Crystallography, Biopharmaceuticals, Discovery, Design and Delivery (BDDD), Medicinal Chemistry and Bioanalysis (MCB) |
| Rok vydání: | 2011 |
| Předmět: |
EXPRESSION
Models Molecular AMMONIA-LYASE Stereochemistry Phenylalanine Stereoisomerism aminomutase Protein Engineering enzyme catalysis Catalysis Enzyme catalysis Substrate Specificity CLONING Turn (biochemistry) chemistry.chemical_compound CHEMISTRY Cinnamates CRYSTAL-STRUCTURE BIOSYNTHESIS Carboxylate directed evolution BETA-AMINO ACIDS Amination Phenylalanine Ammonia-Lyase Regioselectivity General Chemistry General Medicine ss-amino acids MICHAEL ADDITION HISTIDINE chemistry regioselectivity Mutation Michael reaction Taxus |
| Zdroj: | Angewandte Chemie-International Edition, 51(2), 482-486. WILEY-V C H VERLAG GMBH |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | Turn to switch: A mutant of phenylalanine aminomutase was engineered that can catalyze the regioselective amination of cinnamate derivatives (see scheme, red) to, for example, β-amino acids. This regioselectivity, along with the X-ray crystal structures, suggests two distinct carboxylate binding modes differentiated by C(β)-C(ipso) bond rotation, which determines if β- (see scheme) or α-addition takes place. |
| Databáze: | OpenAIRE |
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