Streptavidin-hosted organocatalytic aldol addition

Santi, Nicolò ORCID: https://orcid.org/0000-0001-6361-5457, Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 and Luk, Louis Y. P. ORCID: https://orcid.org/0000-0002-7864-6261 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:	25 Jul 2024 13:14
URI:	https://orca.cardiff.ac.uk/id/eprint/132454

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