Biocatalytic Friedel-Crafts Acylation and Fries Reaction
| Autor: | Nina G. Schmidt, Nina Richter, Karl Gruber, Birgit Wiltschi, Wolfgang Kroutil, Tea Pavkov-Keller |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
DNA
Bacterial arenes biocatalysis Acylation enzymes 010402 general chemistry 01 natural sciences Catalysis Substrate Specificity chemistry.chemical_compound Phenols Pseudomonas Escherichia coli Organic chemistry rearrangements Rearrangement reaction Biocatalysis | Hot Paper Friedel–Crafts reaction 010405 organic chemistry Aryl Communication Regioselectivity General Chemistry General Medicine Communications 0104 chemical sciences Isopropenyl acetate Kinetics chemistry Reagent Acyltransferase Acyltransferases |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 0044-8249 |
| DOI: | 10.1002/ange.201703270 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
| Nepřihlášeným uživatelům se plný text nezobrazuje | K zobrazení výsledku je třeba se přihlásit. |