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Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose‐6‐phosphate Aldolase
Author(s) -
Roldán Raquel,
SanchezMoreno Israel,
Scheidt Thomas,
Hélaine Virgil,
Lemaire Marielle,
Parella Teodor,
Clapés Pere,
Fessner WolfDieter,
GuérardHélaine Christine
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701020
Subject(s) - aldolase a , nucleophile , chemistry , aldolase b , aldol reaction , fructose bisphosphate aldolase , cyclopentanone , substrate (aquarium) , fructose , ketone , anomer , stereoselectivity , stereochemistry , enzyme , organic chemistry , catalysis , oceanography , geology
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.