Pyruvate Aldolases Catalyze Cross-Aldol Reactions between Ketones: Highly Selective Access to Multi-Functionalized Tertiary Alcohols
| Autor: | Mounir Traïkia, Alexandre Uzel, Véronique de Berardinis, Marielle Lemaire, Léa Gourbeyre, Virgil Hélaine, Victor Laurent, Marcel Salanoubat, Thierry Gefflaut, Lionel Nauton, Christine Guérard-Hélaine |
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| Přispěvatelé: | Institut de Chimie de Clermont-Ferrand (ICCF), SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Centre National de la Recherche Scientifique (CNRS), Génomique métabolique (UMR 8030), Genoscope - Centre national de séquençage [Evry] (GENOSCOPE), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université d'Évry-Val-d'Essonne (UEVE) |
| Rok vydání: | 2020 |
| Předmět: |
transaminase
tertiary alcohol pyruvate aldolase [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Context (language use) proline analogue [CHIM.CATA]Chemical Sciences/Catalysis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Aldol reaction Nucleophile chemistry Cascade reaction Electrophile cascade reaction Stereoselectivity Pyruvic acid |
| Zdroj: | ACS Catalysis ACS Catalysis, 2020, 10 (4), pp.2538-2543. ⟨10.1021/acscatal.9b05512⟩ ACS Catalysis, American Chemical Society, 2020, 10 (4), pp.2538-2543. ⟨10.1021/acscatal.9b05512⟩ |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.9b05512 |
| Popis: | International audience; Tertiary alcohols are widely represented in nature and among bioactive molecules. Their importance is attested by the continuous efforts to meet the challenge of their stereoselective synthesis. In this context, we propose an enzymatic approach, involving class II pyruvate aldolases. These enzymes are shown to catalyze selective cross-aldol reactions between pyruvic acid or derivatives as nucleophiles and a series of ketones as electrophiles. This catalytic activity is exemplified by the highly stereoselective preparation of seven branched ketols with good yields. One of them was readily converted into a constrained 4-hydroxyproline analogue in a multienzymatic one-pot one-step process. |
| Databáze: | OpenAIRE |
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