Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose-6-phosphate Aldolase - Université Clermont Auvergne Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2017

Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose-6-phosphate Aldolase

Résumé

D-Fructose-6-phosphate aldolase (FSA) was probed for extended nucleophile promiscuity by using a series of fluorogenic substrates to reveal retro-aldol activity. Four nucleophiles ethanal, propanone, butanone, and cyclopentanone were subsequently confirmed to be non-natural substrates in the synthesis direction using the wild-type enzyme and its D6H variant. This exceptional widening of the nucleophile substrate scope offers a rapid entry, in good yields and high stereoselectivity, to less oxygenated alkyl ketones and aldehydes, which was hitherto impossible.

Dates et versions

hal-01654778 , version 1 (04-12-2017)

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Citer

Raquel Roldán, Israel Sanchez-Moreno, Thomas Scheidt, Virgil Hélaine, Marielle Lemaire, et al.. Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose-6-phosphate Aldolase. Chemistry - A European Journal, 2017, 23 (21), pp.5005 - 5009. ⟨10.1002/chem.201701020⟩. ⟨hal-01654778⟩
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