Encapsulation of a Catalytic Imidazolium Salt into Avidin: Towards the Development of a Biohybrid Catalyst Active in Ionic Liquids

Herein, we report the development of biohybrid catalysts that are capable of catalyzing the aldol reaction. The use of biotinylated imidazolium salts in combination with racemic or enantiomerically pure catalytic anions allowed us to study the adaptive and cooperative positioning of the anionic cata...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-02, Vol.20 (6), p.1530-1538
Main Authors: Gauchot, Vincent, Branca, Mathieu, Schmitzer, Andreea
Format: Article
Language:English
Subjects:
Aldehydes
Aldehydes - chemistry
aldol reaction
Anions
Avidin - chemistry
biotin-avidin
Biotinylation
Catalysis
Catalysts
Chemical reactions
Chemistry
Encapsulation
Imidazoles - chemistry
Ionic liquids
Ionic Liquids - chemistry
Ions
Liquids
Proteins
Salts - chemistry
Solvents
supramolecular catalysis
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Summary:Herein, we report the development of biohybrid catalysts that are capable of catalyzing the aldol reaction. The use of biotinylated imidazolium salts in combination with racemic or enantiomerically pure catalytic anions allowed us to study the adaptive and cooperative positioning of the anionic catalyst inside the protein. Supramolecular encapsulation of the biotinylated catalyst into avidin resulted in good selectivity for the aldol reaction performed in ionic liquid/water mixtures. Biohybrid catalysts capable of catalyzing the aldol reaction are prepared from avidin and biotinylated imidazolium salts with either racemic or enantiomerically pure catalytic anions. Supramolecular encapsulation (see figure) of the biotinylated catalyst in avidin resulted in good selectivities for the aldol reaction when performed in ionic liquid/water mixtures and the adaptive and cooperative positioning of the anionic catalyst inside the avidin protein is discussed.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201303865