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Issue 15, 2021
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Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts

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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 that 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.

Graphical abstract: Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts

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Article information


Submitted
15 Dec 2020
Accepted
14 Jan 2021
First published
14 Jan 2021

This article is Open Access

Chem. Commun., 2021,57, 1919-1922
Article type
Communication

Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts

N. Santi, L. C. Morrill, K. Świderek, V. Moliner and L. Y. P. Luk, Chem. Commun., 2021, 57, 1919
DOI: 10.1039/D0CC08142F

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