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, also known as N3-modified triglycine-lysine hydrochloride, is a synthetic peptide distinguished by the incorporation of an azide-functionalized lysine residue at the C-terminus. The strategic placement of the azide group enables this compound to serve as a versatile molecular tool for bioorthogonal chemistry, particularly in click chemistry applications. Its structure, featuring a triglycine backbone with a terminal azide group, facilitates efficient conjugation to a variety of biomolecules, polymers, or surfaces via copper-catalyzed or strain-promoted azide-alkyne cycloaddition. The peptide's hydrophilic nature and small size further enhance its solubility and compatibility with aqueous biological systems, making it highly attractive for research in chemical biology, proteomics, and material sciences.
Bioorthogonal Labeling: H-Gly-Gly-Gly-Lys(N3) HCl is widely employed in bioorthogonal labeling strategies, where its azide moiety reacts specifically with alkyne-functionalized probes or substrates. This selective reactivity allows researchers to tag proteins, peptides, or other biomolecules in complex biological mixtures without interfering with native biochemical processes. By enabling site-specific conjugation, the peptide facilitates the study of biomolecular interactions, intracellular trafficking, and protein localization through advanced imaging and analytical techniques.
Peptide-Protein Conjugation: The azide-functionalized lysine in this peptide serves as a pivotal handle for constructing peptide-protein conjugates via click chemistry. Researchers can employ it to attach fluorescent dyes, affinity tags, or therapeutic moieties to proteins of interest, thereby expanding the functional repertoire of native proteins. This approach is particularly valuable in the development of biosensors, targeted delivery systems, and protein-based diagnostics, where precise and stable linkage is essential for performance and reproducibility.
Surface Modification: N3-modified triglycine-lysine hydrochloride is instrumental in surface modification protocols for biomaterials and nanoparticles. Its azide group enables robust attachment to alkyne-coated surfaces, resulting in the formation of functionalized interfaces tailored for cell adhesion studies, biosensing platforms, or antifouling coatings. The peptide's compatibility with various substrates, including glass, gold, and polymeric materials, supports the creation of customized surfaces for diverse biomedical and analytical applications.
Proteomics Research: In proteomics, H-Gly-Gly-Gly-Lys(N3) HCl is utilized for selective enrichment and identification of specific protein subsets. By incorporating the peptide into labeling workflows, scientists can introduce unique chemical handles into proteins, facilitating their capture and analysis using azide-alkyne click reactions. This strategy enhances the sensitivity and specificity of proteomic profiling, enabling the discovery of low-abundance proteins, post-translational modifications, and protein-protein interactions within complex biological samples.
Bioconjugate Development: The peptide's azide functionality is a key asset in the synthesis of bioconjugates, such as antibody-drug conjugates, peptide-nanoparticle hybrids, and multifunctional imaging agents. Its efficient and selective conjugation chemistry supports the assembly of complex molecular architectures with defined stoichiometry and spatial arrangement. Researchers leverage these bioconjugates for targeted delivery, enhanced imaging sensitivity, and the creation of multifunctional therapeutic platforms, advancing the frontiers of chemical biology and nanomedicine.
The versatility of H-Gly-Gly-Gly-Lys(N3) HCl is underscored by its broad applicability across multiple scientific disciplines. Its unique chemical structure and reactivity profile make it an indispensable tool for bioorthogonal chemistry, molecular labeling, and the development of advanced biomaterials. Whether employed for selective protein tagging, surface engineering, or the synthesis of innovative bioconjugates, this peptide empowers researchers to design and execute sophisticated experiments that unravel the complexities of biological systems and enable the creation of next-generation analytical and therapeutic technologies.
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