An Artificial Cofactor Catalyzing the Baylis-Hillman Reaction with Designed Streptavidin as Protein Host*.
Baylis-Hillman reaction
artificial cofactors
biocatalysis
protein design
streptavidin
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
04 05 2021
04 05 2021
Historique:
received:
31
12
2020
pubmed:
6
1
2021
medline:
15
12
2021
entrez:
5
1
2021
Statut:
ppublish
Résumé
An artificial cofactor based on an organocatalyst embedded in a protein has been used to conduct the Baylis-Hillman reaction in a buffered system. As protein host, we chose streptavidin, as it can be easily crystallized and thereby supports the design process. The protein host around the cofactor was rationally designed on the basis of high-resolution crystal structures obtained after each variation of the amino acid sequence. Additionally, DFT-calculated intermediates and transition states were used to rationalize the observed activity. Finally, repeated cycles of structure determination and redesign led to a system with an up to one order of magnitude increase in activity over the bare cofactor and to the most active proteinogenic catalyst for the Baylis-Hillman reaction known today.
Identifiants
pubmed: 33400831
doi: 10.1002/cbic.202000880
pmc: PMC8247847
doi:
Substances chimiques
4-(dimethylamine)pyridine
0
Pyridines
0
Streptavidin
9013-20-1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1573-1577Subventions
Organisme : Austrian Science Fund FWF
ID : J 3994
Pays : Austria
Organisme : Austrian Science Fund (FWF, Erwin Schrödinger fellowship
ID : J3994 B21
Organisme : Austrian Science Fund
ID : J3994 B21
Informations de copyright
© 2021 The Authors. ChemBioChem published by Wiley-VCH GmbH.
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