Cardiff University | Prifysgol Caerdydd ORCA
Online Research @ Cardiff 
WelshClear Cookie - decide language by browser settings

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

[thumbnail of molecules-25-02457-v2.pdf]
Preview
PDF - Published Version
Available under License Creative Commons Attribution.

Download (1MB) | Preview

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: 05 May 2023 01:01
URI: https://orca.cardiff.ac.uk/id/eprint/132454

Citation Data

Cited 9 times in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item Edit Item

Downloads

Downloads per month over past year

View more statistics