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

Authors :: Roldán R
Sanchez-Moreno I
Scheidt T
Hélaine V
Lemaire M
Parella T
Clapés P
Fessner WD
Guérard-Hélaine C
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2017 Apr 11; Vol. 23 (21), pp. 5005-5009. Date of Electronic Publication: 2017 Mar 29.
Publication Year :: 2017
Abstract: 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.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Aldehyde-Lyases chemistry
Catalysis
Fructose-Bisphosphate Aldolase chemistry
Molecular Structure
Stereoisomerism
Aldehyde-Lyases metabolism
Aldehydes chemistry
Fructose-Bisphosphate Aldolase metabolism
Fructosephosphates chemistry
Ketones chemistry

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