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Open AccessArticle

Streptavidin-Hosted Organocatalytic Aldol Addition

1
School of Chemistry, Main Building, Cardiff University, Cardiff CF10 3AT, UK
2
Cardiff Catalysis Institute, School of Chemistry, Main Building, Cardiff University, Cardiff CF10 3AT, UK
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Author to whom correspondence should be addressed.
Academic Editor: Isabella Rimoldi
Molecules 2020, 25(10), 2457; https://doi.org/10.3390/molecules25102457
Received: 5 May 2020 / Revised: 18 May 2020 / Accepted: 20 May 2020 / Published: 25 May 2020
(This article belongs to the Special Issue Hybrid Catalysts for Asymmetric Catalysis)
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. View Full-Text
Keywords: organocatalysis; streptavidin; artificial enzyme; protein; aldol; enamine; catalysis; biocompatible organocatalysis; streptavidin; artificial enzyme; protein; aldol; enamine; catalysis; biocompatible
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MDPI and ACS Style

Santi, N.; Morrill, L.C.; Luk, L.Y.P. Streptavidin-Hosted Organocatalytic Aldol Addition. Molecules 2020, 25, 2457.

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