Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts
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comunitat-uji-handle2:10234/7013
comunitat-uji-handle3:10234/8638
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INVESTIGACIONMetadata
Title
Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalystsDate
2021-02-21Publisher
Royal Society of ChemistryISSN
1359-7345; 1364-548XBibliographic citation
Santi, N., Morrill, L. C., Świderek, K., Moliner, V., & Luk, L. Y. (2021). Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts. Chemical Communications, 57(15), 1919-1922.Type
info:eu-repo/semantics/articleVersion
info:eu-repo/semantics/publishedVersionSubject
Abstract
Here, the streptavidin–biotin technology was applied to enable
organocatalytic transfer hydrogenation. By introducing a biotintethered pyrrolidine (1) to the tetrameric streptavidin (T-Sav), the
resulting hybrid ... [+]
Here, the streptavidin–biotin technology was applied to enable
organocatalytic transfer hydrogenation. By introducing a biotintethered pyrrolidine (1) to the tetrameric streptavidin (T-Sav), the
resulting hybrid catalyst was able to mediate hydride transfer from
dihydro-benzylnicotinamide (BNAH) to a,b-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. [-]
Is part of
Chemical Communication, Vol. 57 (2021)Funder Name
Cardiff School of Chemistry, Cardiff University | Royal Society | UK’s Wellcome Trust
Project code
RPG-2017-195 | RG150466 | 202056/Z/16/Z
Rights
This journal is © The Royal Society of Chemistry 2021
info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
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- QFA_Articles [825]
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