Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions
| Autor: | Marcel Frese, Christian Schnepel, Hannah Minges, Norbert Sewald, Hauke Voß, Rebecca C. Feiner |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
inorganic chemicals
reactions biocatalysis Aryl halide Substituent multicomponent 010402 general chemistry 01 natural sciences enzyme catalysis Catalysis Coupling reaction Enzyme catalysis Inorganic Chemistry chemistry.chemical_compound cross-coupling Organic chemistry Physical and Theoretical Chemistry chemistry.chemical_classification 010405 organic chemistry Aryl Organic Chemistry Halogenation palladium 0104 chemical sciences chemistry Biocatalysis Boronic acid |
| Popis: | The combination of the biocatalytic halogenation of l-tryptophan with subsequent chemocatalytic Suzuki-Miyaura crosscoupling reactions leads to the modular synthesis of an array of C5, C6, or C7 aryl-substituted tryptophan derivatives. In a three-step one-pot reaction, the bromo substituent is initially incorporated regioselectively by immobilized tryptophan 5-, 6-, or 7-halogenases, respectively, with concomitant cofactor regeneration. The halogenation proceeds in aqueous media at room temperature in the presence of NaBr and O-2. After the separation of the biocatalyst by filtration, a Pd catalyst, base, and boronic acid are added to the aryl halide formed in situ to effect direct Suzuki-Miyaura cross-coupling reactions followed by tert-butoxycarbonyl (Boc) protection. After a single purification step, different Boc-protected aryl tryptophan derivatives are obtained that can, for example, be used for peptide or peptidomimetic synthesis. |
| Databáze: | OpenAIRE |
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