Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host
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Other documents of the author: Nödling, Alexander; Świderek, Katarzyna; Castillo, Raquel; Hall, Jonathan W.; Angelastro, Antonio; Morrill, Louis; Tsai, Yu-Hsuan; Moliner, Vicent; Luk, Louis Y. P.
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comunitat-uji-handle3:10234/8638
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Title
Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein HostAuthor (s)
Date
2018-09-17Publisher
WileyISSN
1433-7851; 1521-3773Bibliographic citation
NÖDLING, Alexander R., et al. Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host. Angewandte Chemie International Edition, 2018, vol. 57, no 38, p. 12478-12482Type
info:eu-repo/semantics/articlePublisher version
https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201806850Version
info:eu-repo/semantics/publishedVersionSubject
Abstract
There has been growing interest in performing organocatalysis within a supramolecular system as a means of controlling reaction reactivity and stereoselectivity. Here, a protein is used as a host for iminium catalysis. ... [+]
There has been growing interest in performing organocatalysis within a supramolecular system as a means of controlling reaction reactivity and stereoselectivity. Here, a protein is used as a host for iminium catalysis. A pyrrolidine moiety is covalently linked to biotin and introduced to the protein host streptavidin for organocatalytic activity. Whereas in traditional systems stereoselectivity is largely controlled by the substituents added to the organocatalyst, enantiomeric enrichment by the reported supramolecular system is completely controlled by the host. Also, the yield of the model reaction increases over 10-fold when streptavidin is included. A 1.1 angstrom crystal structure of the protein-catalyst complex and molecular simulations of a key intermediate reveal the chiral scaffold surrounding the organocatalytic reaction site. This work illustrates that proteins can be an excellent supramolecular host for driving stereoselective secondary amine organo-catalysis. [-]
Is part of
Angewandte Chemie International Edition, 2018, vol. 57, no 38Investigation project
Leverhulme Trust. Grant Number: RPG-2017-195; Royal Society Grant. Grant Number: RG150466; Wellcome Trust. Grant Numbers: 202056/Z/16/Z, 200730/Z/16/Z; Spanish Ministerio de Economía y Competitividad. Grant Number: CTQ2015-66223-C2; Juan de la Cierva-Incorporación. Grant Number: IJCI-2016-27503; Universitat Jaume I. Grant Number: Project UJI·B2017- 31Rights
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
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