Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst

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

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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
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:	07 May 2023 07:30
URI:	https://orca.cardiff.ac.uk/id/eprint/137693

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