H-Gly-Gly-Gly-Lys(N3) HCl is a tetrapeptide featuring an azido-modified lysine side chain enabling bioorthogonal conjugation. Researchers use it to explore click-chemistry labeling, flexible backbone behavior, and solvent interactions. The peptide's simplicity supports versatile mechanistic evaluations.
CAT No: R2496
CAS No:2737202-70-7
Synonyms/Alias:H-Gly-Gly-Gly-Lys(N3) HCl;2737202-70-7;H-(Gly)3-Lys(N3)-OH hydrochloride;H-(Gly)3-Lys(N3)-OH (hydrochloride);(2S)-2-[[2-[[2-[(2-aminoacetyl)amino]acetyl]amino]acetyl]amino]-6-azidohexanoic acid;hydrochloride;HY-151782A;DA-73977;CS-0619855;
H-Gly-Gly-Gly-Lys(N3) HCl is a synthetic peptide featuring a sequence of three glycine residues followed by a lysine residue modified at the side chain with an azide (N3) group, presented as its hydrochloride salt. As a versatile peptide building block, it holds significant value in chemical biology, peptide engineering, and bioconjugation research. The azide-functionalized lysine residue enables site-specific chemical modification, making this compound particularly relevant for applications involving bioorthogonal chemistry and advanced labeling strategies. Its well-defined structure and functional handle support a range of experimental designs, from molecular probe development to the creation of multifunctional biomolecules.
Bioorthogonal labeling: The azide group on the lysine side chain provides a highly selective chemical handle for copper-catalyzed azide-alkyne cycloaddition (CuAAC) and strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. Researchers use this peptide as a substrate or intermediate for site-specific conjugation of fluorophores, affinity tags, or other molecular probes, enabling precise labeling of peptides, proteins, or other biomolecules in complex biological systems. This capability is essential for tracking molecular interactions, visualizing cellular processes, and studying protein localization with minimal perturbation to native structures.
Peptide conjugate synthesis: The unique structure of H-Gly-Gly-Gly-Lys(N3) HCl makes it an ideal precursor for constructing multifunctional peptide conjugates. Its N-terminal glycine-rich sequence offers flexibility and reduced steric hindrance, facilitating efficient coupling reactions, while the azide moiety allows for modular assembly with a wide variety of alkyne-functionalized molecules. This property is exploited in the synthesis of peptide-drug conjugates, targeted delivery systems, and peptide-based biomaterials, where precise spatial arrangement of functional groups is crucial for activity and selectivity.
Protein engineering and site-specific modification: Incorporation of this azide-functionalized peptide into larger polypeptides or recombinant proteins enables controlled site-specific modifications. By introducing the sequence genetically or via chemical ligation, researchers can achieve selective attachment of functional entities such as polyethylene glycol (PEG), imaging agents, or crosslinkers at defined positions. This approach is instrumental in the development of modified proteins with enhanced pharmacokinetic properties, improved stability, or novel functionalities for biochemical assays and biotechnological applications.
Click chemistry-based immobilization: The azide group in the peptide facilitates robust and oriented immobilization of biomolecules onto surfaces or nanoparticles through click chemistry. This application is particularly valuable in the fabrication of peptide microarrays, biosensors, and affinity chromatography matrices. The specificity of the azide-alkyne reaction ensures stable attachment while preserving the biological activity of the immobilized peptide, thereby enhancing assay reproducibility and sensitivity in analytical and diagnostic workflows.
Molecular probe and sensor development: The modularity offered by the azide functionality supports the design of custom molecular probes and biosensors. By coupling the peptide to various reporter groups or sensing elements via click chemistry, researchers can generate tailored probes for detecting enzymatic activity, monitoring cellular uptake, or interrogating protein-protein interactions. The small and inert nature of the glycine-rich sequence minimizes background interference, enabling high-contrast readouts and reliable data acquisition in complex biological samples.
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