TY - JOUR
T1 - Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose-6-phosphate Aldolase
AU - Roldán, Raquel
AU - Sanchez-Moreno, Israel
AU - Scheidt, Thomas
AU - Hélaine, Virgil
AU - Lemaire, Marielle
AU - Parella, Teodor
AU - Clapés, Pere
AU - Fessner, Wolf Dieter
AU - Guérard-Hélaine, Christine
PY - 2017/4/11
Y1 - 2017/4/11
N2 - © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
AB - © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
KW - aldolization
KW - biocatalysis
KW - enzymes
KW - fructose-6-phosphate aldolase
KW - phosphorylated compounds
U2 - 10.1002/chem.201701020
DO - 10.1002/chem.201701020
M3 - Article
VL - 23
SP - 5005
EP - 5009
IS - 21
ER -