H-Arg-Arg-Arg-Arg-Arg-Arg-OH is a highly cationic hexapeptide rich in guanidinium groups, frequently used to model nucleic-acid and membrane interactions. Strong electrostatics drive association with anionic biomolecules. Researchers probe its role in cell-penetrating and condensation-like behavior in vitro. Applications include polycation research, peptide-DNA binding studies, and electrostatic-assembly modeling.
CAT No: R2367
CAS No:96337-25-6
Synonyms/Alias:H-Arg-Arg-Arg-Arg-Arg-Arg-OH;Hexaarginine;96337-25-6;(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid;CHEMBL2049164;Arg-Arg-Arg-Arg-Arg-Arg;BDBM50387012;DA-74101;FA109316;(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoic acid;
H-Arg-Arg-Arg-Arg-Arg-Arg-OH is a synthetic hexapeptide composed entirely of arginine residues, commonly referred to as polyarginine (R6). As a homopolymeric peptide, it is characterized by its high density of guanidinium groups, which confer a strong cationic nature and facilitate diverse interactions with biological molecules and membranes. Its well-defined sequence and physicochemical properties make it a valuable tool in peptide research, particularly in studies exploring peptide-membrane interactions, cellular uptake mechanisms, and the functionalization of biomolecules. The versatility and modularity of this peptide enable its use in a broad range of experimental contexts within molecular biology, biochemistry, and materials science.
Cell-Penetrating Peptide Research: Polyarginine peptides, such as R6, are extensively utilized in the investigation of cell-penetrating peptides (CPPs). Their ability to traverse cellular membranes is attributed to the presence of multiple arginine residues, which engage in electrostatic interactions with negatively charged phospholipids on the cell surface. Researchers employ R6 as a model system to study the uptake efficiency, mechanism of internalization, and structure-activity relationships of arginine-rich CPPs. Insights gained from these studies inform the design of novel delivery vectors for macromolecules, nucleic acids, or imaging agents in a research setting.
Molecular Delivery Vehicle Development: The hexapeptide structure of polyarginine enables it to function as a carrier for the intracellular delivery of various cargoes, including proteins, oligonucleotides, and nanoparticles. By covalently or non-covalently attaching bioactive molecules to R6, scientists can enhance cellular uptake and promote efficient translocation across biological barriers in vitro. Such applications are critical for developing experimental delivery systems and for optimizing protocols that require the introduction of exogenous materials into cells for mechanistic studies or high-content screening.
Biophysical and Structural Studies: The unique charge properties and conformational flexibility of polyarginine peptides make them ideal for probing peptide-membrane interactions and electrostatic phenomena. R6 is frequently employed in model membrane systems and biophysical assays to elucidate the dynamics of peptide binding, membrane disruption, and aggregation. These studies contribute to a deeper understanding of the fundamental principles governing peptide-lipid interactions and inform the rational design of membrane-active biomolecules.
Peptide Functionalization and Conjugation: The availability of multiple guanidinium groups in polyarginine provides versatile sites for chemical modification and conjugation. Researchers utilize R6 as a scaffold for the attachment of fluorophores, affinity tags, or other functional moieties, facilitating the creation of multifunctional peptide constructs. Such functionalized peptides are instrumental in applications ranging from fluorescence microscopy and flow cytometry to affinity purification and surface immobilization in biosensor development.
Proteomics and Analytical Applications: In proteomics workflows, polyarginine peptides serve as calibration standards or as affinity capture reagents due to their predictable mass and strong binding affinities. Their consistent physicochemical properties and sequence homogeneity make them suitable for mass spectrometry calibration, method validation, and as controls in peptide quantification assays. The use of R6 in these analytical contexts supports the generation of robust, reproducible data and enhances the reliability of peptide-based analytical techniques.
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