Expanding the Genetic Code: Incorporation of Functional Secondary Amines via Stop Codon Suppression
Abstract: Enzymes are attractive catalysts for chemical industries, and their use has become a mature alternative to conventional chemical methods. However, biocatalytic approaches are often restricted to metabolic and less complex reactivities, given the limited amount of functional groups present. This drawback can be addressed by incorporating non‐canonical amino acids (ncAAs) harboring new‐to‐nature chemical groups. Inspired by organocatalysis, we report the design, synthesis and characterization of a panel of ncAAs harboring functional secondary amines and their cellular incorporation into different protein scaffolds. D/L‐pyrrolidine‐ and D/L‐piperidine‐based ncAAs were successfully site‐specifically incorporated into proteins via stop codon suppression methodology. To demonstrate the utility of these ncAAs, the catalytic performance of the obtained artificial enzymes was investigated in a model Michael addition reaction. The incorporation of pyrrolidine‐ and piperidine‐ based ncAAs significantly expands the available toolbox for protein engineering and chemical biology applications.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Expanding the Genetic Code: Incorporation of Functional Secondary Amines via Stop Codon Suppression ; day:10 ; month:10 ; year:2023 ; extent:8
ChemCatChem ; (10.10.2023) (gesamt 8)
- Creator
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Gran‐Scheuch, Alejandro
Bonandi, Elisa
Drienovská, Ivana
- DOI
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10.1002/cctc.202301004
- URN
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urn:nbn:de:101:1-2023101015300792805411
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:51 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Gran‐Scheuch, Alejandro
- Bonandi, Elisa
- Drienovská, Ivana
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Extended stop codon context predicts nonsense codon readthrough efficiency in human cells
Stereoselective chemical N-glycoconjugation of amines via CO2 incorporation
Environment modulates protein heterogeneity through transcriptional and translational stop codon readthrough
Selective forces and mutational biases drive stop codon usage in the human genome: a comparison with sense codon usage
Functional consequences of DECTIN-1early stop codon polymorphism Y238X in rheumatoid arthritis
Mining prokaryotic genomes for unknown amino acids: a stop-codon-based approach
Cα–H Oxidations of Amines to Amides: Expanding Mechanistic Understanding and Amine Scope through Catalyst Development
Sense codon emancipation for proteome-wide incorporation of noncanonical amino acids : Rare isoleucine codon AUA as a target for genetic code expansion
Translational quality control mechanisms that mitigate stop codon readthrough and ensure protein homeostasis
Systematic and quantitative analysis of stop codon readthrough in Rett syndrome nonsense mutations
Genome-scale quantification and prediction of pathogenic stop codon readthrough by small molecules
Stops making sense: translational trade-offs and stop codon reassignment
Extended stop codon context predicts nonsense codon readthrough efficiency in human cells
Stereoselective chemical N-glycoconjugation of amines via CO2 incorporation
Environment modulates protein heterogeneity through transcriptional and translational stop codon readthrough
Selective forces and mutational biases drive stop codon usage in the human genome: a comparison with sense codon usage
Functional consequences of DECTIN-1early stop codon polymorphism Y238X in rheumatoid arthritis
Mining prokaryotic genomes for unknown amino acids: a stop-codon-based approach
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Sense codon emancipation for proteome-wide incorporation of noncanonical amino acids : Rare isoleucine codon AUA as a target for genetic code expansion
Translational quality control mechanisms that mitigate stop codon readthrough and ensure protein homeostasis
Systematic and quantitative analysis of stop codon readthrough in Rett syndrome nonsense mutations