Streptavidin-Hosted Organocatalytic Aldol Addition
Copyright policy )Streptavidin-Hosted Organocatalytic Aldol Addition
In this report, the streptavidin-biotin technology was applied to enable organocatalytic aldol addition. By attaching pyrrolidine to the valeric motif of biotin and introducing it to streptavidin (Sav), a protein-based organocatalytic system was created, and the aldol addition of acetone with p-nitrobenzaldehyde was tested. The conversion of substrate to product can be as high as 93%. Although the observed enantioselectivity was only moderate (33:67 er), further protein engineering efforts can be included to improve the selectivity. These results have proven the concept that Sav can be used to host stereoselective aldol addition.
- University of Modena and Reggio Emilia Italy
- Cardiff University United Kingdom
- Cardiff University
Models, Molecular, Pyrrolidines, Protein Conformation, biocompatible, Organic chemistry, Biotin, Chemistry Techniques, Synthetic, Article, Acetone, QD241-441, streptavidin, Humans, organocatalysis, Aldol; Artificial enzyme; Biocompatible; Catalysis; Enamine; Organocatalysis; Protein; Streptavidin, artificial enzyme, Aldehydes, catalysis, enamine, Stereoisomerism, Benzaldehydes, aldol, Streptavidin, protein
Models, Molecular, Pyrrolidines, Protein Conformation, biocompatible, Organic chemistry, Biotin, Chemistry Techniques, Synthetic, Article, Acetone, QD241-441, streptavidin, Humans, organocatalysis, Aldol; Artificial enzyme; Biocompatible; Catalysis; Enamine; Organocatalysis; Protein; Streptavidin, artificial enzyme, Aldehydes, catalysis, enamine, Stereoisomerism, Benzaldehydes, aldol, Streptavidin, protein
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