Pyruvate Aldolases Catalyze Cross-Aldol Reactions between Ketones: Highly Selective Access to Multi-Functionalized Tertiary Alcohols - Université Clermont Auvergne Accéder directement au contenu
Article Dans Une Revue ACS Catalysis Année : 2020

Pyruvate Aldolases Catalyze Cross-Aldol Reactions between Ketones: Highly Selective Access to Multi-Functionalized Tertiary Alcohols

Résumé

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.
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hal-02907546 , version 1 (01-12-2020)

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Victor Laurent, Léa Gourbeyre, Alexandre Uzel, Virgil Hélaine, Lionel Nauton, et al.. Pyruvate Aldolases Catalyze Cross-Aldol Reactions between Ketones: Highly Selective Access to Multi-Functionalized Tertiary Alcohols. ACS Catalysis, 2020, 10 (4), pp.2538-2543. ⟨10.1021/acscatal.9b05512⟩. ⟨hal-02907546⟩
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