Santi, Nicolò  ORCID: https://orcid.org/0000-0001-6361-5457, Morrill, Louis Christian ORCID: https://orcid.org/0000-0002-6453-7531, Swiderek, Katarzyna, Moliner, Vicent and Luk, Louis Y. P. ORCID: https://orcid.org/0000-0002-7864-6261
2021.
Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst.
Chemical Communications
57
(15)
, pp. 1919-1922.
10.1039/D0CC08142F
|
Preview |
PDF
- Published Version
Available under License Creative Commons Attribution. Download (1MB) | Preview |
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 |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry Research Institutes & Centres > 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: | 07 May 2023 07:30 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/137693 |
Citation Data
Cited 10 times in Scopus. View in Scopus. Powered By Scopus® Data
Actions (repository staff only)
 |
Edit Item |
Dimensions
Dimensions