Santi, Nicolò, Morrill, Louis Christian, Swiderek, Katarzyna, Moliner, Vicent and Luk, Louis Y. P.
2021.
Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst.
Chemical Communications
57
(15)
, pp. 1919-1922.
10.1039/D0CC08142F
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Abstract
Here, the streptavidin-biotin technology was applied to enable organocatalytic transfer hydrogenation. By introducing a biotin-tethered pyrrolidine (1) to the tetrameric streptavidin (T-Sav), the resulting hybrid catalyst was able to mediate hydride transfer from dihydro-benzylnicotinamide (BNAH) to α, β-unsaturated aldehydes. Hydrogenation of cinnamaldehyde and some of its aryl-substituted analogues was found to be nearly quantitative. Kinetic measurements revealed that the T-Sav:1 assembly possesses enzyme-like behavior, whereas isotope effect analysis, performed by QM/MM simulations, illustrated the step of hydride transfer is at least partially rate-limiting. These results have proven the concept that T-Sav can be used to host secondary amine-catalyzed transfer hydrogenations.
Item Type: | Article |
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Date Type: | Publication |
Status: | Published |
Schools: | Chemistry Cardiff Catalysis Institute (CCI) |
Publisher: | Royal Society of Chemistry |
ISSN: | 1359-7345 |
Funders: | Leverhulme Trust, The Royal Society, Wellcome Trust |
Date of First Compliant Deposit: | 15 January 2021 |
Date of Acceptance: | 14 January 2021 |
Last Modified: | 30 Jan 2022 10:29 |
URI: | https://orca.cardiff.ac.uk/id/eprint/137693 |
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