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Streptavidin-Hosted Organocatalytic Aldol Addition
Nicolò Santi1, Louis C Morrill1,2, Louis Y P Luk1,2
1School of Chemistry, Main Building, Cardiff University, Cardiff CF10 3AT, UK.
Abstract:
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.
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