TY - JOUR
T1 - Biocatalytic Friedel-Crafts Acylation and Fries Reaction
AU - Schmidt, Nina G.
AU - Pavkov-Keller, Tea
AU - Richter, Nina
AU - Wiltschi, Birgit
AU - Gruber, Karl
AU - Kroutil, Wolfgang
PY - 2017/5/23
Y1 - 2017/5/23
N2 - The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C−C bond formation methods.
AB - The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C−C bond formation methods.
UR - http://europepmc.org/abstract/med/28544673
U2 - 10.1002/anie.201703270
DO - 10.1002/anie.201703270
M3 - Article
C2 - 28544673
SN - 1433-7851
VL - 56
SP - 7615
EP - 7619
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 26
ER -