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Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation
- Source :
- Nature Communications, Nature Communications, Vol 12, Iss 1, Pp 1-9 (2021)
- Publication Year :
- 2021
- Publisher :
- Nature Publishing Group UK, 2021.
-
Abstract
- Naturally abundant quinones are important molecules, which play essential roles in various biological processes due to their reduction potential. In contrast to their universality, the investigation of reactions between quinones and proteins remains sparse. Herein, we report the development of a convenient strategy to protein modification via a biomimetic quinone-mediated oxidation at the N-terminus. By exploiting unique reactivity of an ortho-quinone reagent, the α-amine of protein N-terminus is oxidized to generate aldo or keto handle for orthogonal conjugation. The applications have been demonstrated using a range of proteins, including myoglobin, ubiquitin and small ubiquitin-related modifier 2 (SUMO2). The effect of this method is further highlighted via the preparation of a series of 17 macrophage inflammatory protein 1β (MIP-1β) analogs, followed by preliminary anti-HIV activity and cell viability assays, respectively. This method offers an efficient and complementary approach to existing strategies for N-terminal modification of proteins.<br />Methods for selective modification of the N-terminus of proteins are of high interest, but mostly require specific amino acid residues. Here, the authors report a selective and fast method for N-terminal modification of proteins based on quinone-mediated oxidation of the alpha-amine to aldehyde or ketone, and apply it to diverse proteins.
- Subjects :
- Science
General Physics and Astronomy
Medicinal chemistry
HIV Infections
SUMO2
010402 general chemistry
Virus Replication
01 natural sciences
Antiviral Agents
General Biochemistry, Genetics and Molecular Biology
Article
chemistry.chemical_compound
Ubiquitin
Biomimetic Materials
Biomimetics
Cell Line, Tumor
Humans
Reactivity (chemistry)
Viability assay
Amines
Chemokine CCL4
Multidisciplinary
biology
010405 organic chemistry
Myoglobin
Quinones
Proteins
General Chemistry
Combinatorial chemistry
Recombinant Proteins
0104 chemical sciences
Quinone
chemistry
Reagent
biology.protein
HIV-1
Small Ubiquitin-Related Modifier Proteins
Amine gas treating
Peptides
Oxidation-Reduction
Protein Processing, Post-Translational
Chemical modification
Subjects
Details
- Language :
- English
- ISSN :
- 20411723
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Nature Communications
- Accession number :
- edsair.doi.dedup.....3f56dee2bdcb45265e6ae9c7c8b8399b