AzGGK is a short peptide bearing azido functionality for click-chemistry conjugation. Glycine spacers offer flexibility, while lysine provides a reactive amine handle for derivatization. Researchers employ it to create labeled peptides, hydrogels, and bioconjugates. Applications include probe development, materials chemistry, and modular peptide synthesis.
CAT No: R2609
CAS No:2407768-11-8
Synonyms/Alias:AzGGK;N6-((2-azidoacetyl)glycyl)-L-lysine;2407768-11-8;N6-[(2-Azidoacetyl)glycyl]-L-lysine HCl;SCHEMBL21611915;GLXC-20772;DA-50865;HY-148835;CS-0642777;(2S)-2-amino-6-[[2-[(2-azidoacetyl)amino]acetyl]amino]hexanoic acid;
AzGGK, or azido-glycyl-glycyl-lysine, is a synthetic peptide derivative featuring an N-terminal azido group and a lysine residue at the C-terminus. Structurally, it belongs to the class of custom-designed tripeptides, engineered to introduce bioorthogonal functional groups into peptide chains or proteins. The presence of the azido moiety provides a chemically reactive handle for selective conjugation, while the peptide backbone offers compatibility with biological systems and peptide-based research. AzGGK is particularly valued in chemical biology and peptide engineering for its utility in site-specific labeling, crosslinking, and functional studies involving protein-protein interactions or post-translational modifications.
Bioorthogonal labeling: One of the primary applications of AzGGK is in bioorthogonal labeling strategies, where its azido group serves as a reactive site for click chemistry reactions, such as copper-catalyzed azide-alkyne cycloaddition (CuAAC) or strain-promoted azide-alkyne cycloaddition (SPAAC). Researchers can incorporate this tripeptide into proteins or peptides, enabling selective conjugation with alkyne-functionalized probes, fluorophores, or affinity tags under mild conditions. This facilitates the visualization, tracking, or enrichment of modified biomolecules in complex biological samples without interfering with native biochemical processes.
Peptide synthesis and modification: In solid-phase peptide synthesis (SPPS) and related methodologies, AzGGK is used as a building block to introduce azido functionality at defined positions within peptide chains. Its incorporation allows for subsequent chemoselective ligations, crosslinking, or functionalization steps, expanding the structural diversity and functional repertoire of synthetic peptides. This capability is crucial for the development of peptide libraries, multifunctional bioconjugates, and advanced biomaterials.
Protein-protein interaction studies: The unique chemical reactivity of AzGGK makes it a valuable tool for probing protein-protein interactions through covalent crosslinking. By integrating the azido-containing tripeptide at specific sites within a protein or peptide, researchers can capture transient or weak interactions via subsequent click-based crosslinking. This approach provides mechanistic insights into complex assemblies, signaling pathways, or structural dynamics that are otherwise challenging to characterize using conventional non-covalent methods.
Post-translational modification (PTM) mimetics: AzGGK can be used to mimic or study lysine modifications, such as ubiquitination or sumoylation, by serving as a substrate analog or as a site for the introduction of synthetic PTMs. The lysine residue at the C-terminus is particularly relevant for exploring modification-dependent signaling, recognition, or degradation pathways. Incorporation of this tripeptide into model substrates enables detailed investigation of enzyme specificity, substrate recognition, and the functional consequences of lysine-targeted modifications.
Proteomics and analytical applications: The azido-functionalized peptide is also applied in proteomics workflows, where it aids in the selective enrichment, detection, or quantification of target proteins or peptides. Through click chemistry-based capture, AzGGK-modified biomolecules can be isolated from complex mixtures, enhancing the sensitivity and specificity of downstream mass spectrometry or immunoassay analyses. This targeted approach supports advanced studies in protein profiling, biomarker discovery, and functional proteomics, allowing for a deeper understanding of cellular processes at the molecular level.
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