Journal
MOLECULES
Volume 25, Issue 10, Pages -Publisher
MDPI
DOI: 10.3390/molecules25102457
Keywords
organocatalysis; streptavidin; artificial enzyme; protein; aldol; enamine; catalysis; biocompatible
Funding
- Cardiff University through the Cardiff School of Chemistry
- Leverhulme Trust [RPG-2017-195]
- Royal Society [RG150466]
- UK's Wellcome Trust [202056/Z/16/Z]
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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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