Arginylserylarginine is a tripeptide carrying two arginines flanking a polar serine, generating a highly cationic yet hydrogen-bond-rich motif. The sequence supports nucleic-acid binding and protein-surface interaction studies. Researchers explore its conformational freedom and electrostatic association in solution. Applications include peptide-DNA binding models, cell-penetrating motif analysis, and charge-distribution research.
CAT No: R2578
CAS No:115035-42-2
Synonyms/Alias:arginylserylarginine;115035-42-2;H-ARG-SER-ARG-OH ACETATE SALT;2-[[2-[[2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid;DTXSID80400201;VENMDXUVHSKEIN-UHFFFAOYSA-N;DA-53840;N~5~-(Diaminomethylidene)ornithylseryl-N~5~-(diaminomethylidene)ornithine;
Arginylserylarginine is a synthetic tripeptide composed of arginine, serine, and arginine residues arranged in a specific sequence. As a member of the peptide compound class, it features both basic and polar side chains, conferring unique physicochemical properties that make it an attractive tool for research in peptide biochemistry. The presence of two arginine residues flanking a central serine introduces multiple sites for hydrogen bonding, electrostatic interactions, and potential post-translational modifications. Researchers utilize such tripeptides to probe structure-function relationships, investigate peptide-protein interactions, and explore mechanisms underlying peptide-mediated cellular processes.
Peptide-protein interaction studies: The tripeptide structure of arginylserylarginine serves as a valuable probe for examining specific binding motifs in protein recognition domains. Its combination of basic and polar side chains enables detailed investigation into the molecular determinants of binding affinity and selectivity, particularly in systems where arginine-rich motifs are implicated in cellular signaling or nucleic acid interactions. Researchers can employ this peptide in binding assays to map interaction sites, dissect recognition motifs, and elucidate the contribution of individual amino acid residues to overall binding dynamics.
Peptide synthesis and method development: As a defined tripeptide, arginylserylarginine is frequently used as a model substrate in the development and optimization of peptide synthesis protocols. Its sequence, containing both charged and uncharged residues, provides a relevant test case for evaluating coupling efficiency, protecting group strategies, and purification methods in solid-phase or solution-phase peptide synthesis. By studying the synthesis and handling of this peptide, chemists can refine methodologies applicable to more complex peptide constructs.
Enzymatic substrate specificity assays: The unique sequence of arginylserylarginine makes it an informative substrate for studying the specificity of proteases, peptidases, and other peptide-modifying enzymes. Its arginine termini are recognized by a variety of endopeptidases, while the central serine offers a potential site for phosphorylation or other modifications. Researchers can utilize this tripeptide to characterize enzyme kinetics, define substrate preferences, and screen for inhibitors or modulators in enzymology research.
Biochemical pathway elucidation: In studies of arginine- and serine-related metabolic or signaling pathways, arginylserylarginine can function as a tool for tracing biochemical transformations or mapping post-translational modifications. Its defined sequence allows for precise monitoring in analytical workflows such as mass spectrometry or HPLC, supporting efforts to identify metabolic intermediates, characterize modification patterns, or validate pathway-specific analytical methods.
Peptide-based functional studies: The physicochemical features of arginylserylarginine, including its charge distribution and hydrogen bonding capacity, make it suitable for exploring the effects of small peptides on membrane dynamics, cellular uptake, or molecular self-assembly. Researchers can employ this tripeptide to investigate mechanisms of peptide transport, aggregation, or interaction with biological membranes, providing insights into the broader roles of short peptides in cellular and molecular biochemistry.
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