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Streptavidin-hosted organocatalytic aldol addition

Santi, Nicolò, Morrill, Louis C. and Luk, Louis Y. P. 2020. Streptavidin-hosted organocatalytic aldol addition. Molecules 25 (10) , 2457. 10.3390/molecules25102457

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: MDPI
ISSN: 1420-3049
Funders: Leverhulme Trust, Royal Society, Wellcome Trust
Date of First Compliant Deposit: 15 June 2020
Date of Acceptance: 20 May 2020
Last Modified: 31 Jul 2020 16:08
URI: http://orca.cf.ac.uk/id/eprint/132454

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