Pyruvate aldolases catalyze cross-aldol reactions between ketones: Highly selective access to multi-functionalized tertiary alcohols

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논문

Pyruvate aldolases catalyze cross-aldol reactions between ketones: Highly selective access to multi-functionalized tertiary alcohols

학술지

ACS catalysis

저자명

Laurent, Victor; Gourbeyre, Lé a; Uzel, Alexandre; Hé laine, Virgil; Nauton, Lionel; Traï kia, Mounir; de Berardinis, Vé ronique; Salanoubat, Marcel; Gefflaut, Thierry; Lemaire, Marielle; Gué rard-Hé laine, Christine

초록

<P>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.</P><BR>[FIG OMISSION]</BR>

발행연도

2020

발행기관

American Chemical Society

ISSN

2155-5435

권

페이지

pp.2538-2543

DOI

10.1021/acscatal.9b05512

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