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Biocatalytic Friedel-Crafts Acylation and Fries Reaction.

ABSTRACT: 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.

SUBMITTER: Schmidt NG

PROVIDER: S-EPMC5488191 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Biocatalytic Friedel-Crafts Acylation and Fries Reaction.

Schmidt Nina G NG Pavkov-Keller Tea T Richter Nina N Wiltschi Birgit B Gruber Karl K Kroutil Wolfgang W

Angewandte Chemie (International ed. in English) 20170523 26

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 enzy ...[more]

PMID: 28544673

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