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

AuthorsRoldán, Raquel; Sánchez-Moreno, Israel ; Scheidt, Thomas; Hélaine, Virgil; Lemaire, Marielle; Parella, T.; Clapés Saborit, Pere ; Fessner, Wolf Dieter; Guérard-Hélaine, Christine
KeywordsSimple Aliphatic Ketones
fructose-6-phosphate aldolase
phosphorylated compounds
Issue Date11-Apr-2017
CitationChemistry - a European Journal 23 (21): 5005-5009 (2017)
Abstractd-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. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Publisher version (URL)10.1002/chem.201701020
Appears in Collections:(IQAC) Artículos
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