Lysyllysyllysine provides a tricationic tripeptide featuring three lysine residues, generating high charge density and strong electrostatic behavior. Researchers investigate its interactions with nucleic acids, acidic proteins, and membranes. Its flexibility supports modeling of polycationic binding motifs. Applications include chromatin research, peptide-polymer assemblies, and charge-driven interaction analysis.
CAT No: R2366
CAS No:13184-14-0
Synonyms/Alias:Lysyllysyllysine;Lys-Lys-Lys;13184-14-0;Trilysine;l-lysyl-l-lysyl-l-lysine;L-Lysine, L-lysyl-L-lysyl-;H-Lys-Lys-Lys-OH Acetate Salt;lysyl-lysyl-lysine;UNII-Y7F82M80K8;25988-63-0;Y7F82M80K8;(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoic acid;(S)-6-Amino-2-((S)-6-amino-2-((S)-2,6-diaminohexanamido)hexanamido)hexanoic acid;Lysyllysyllysine?;2olb;POLYLYSINE HBR;L-Lysine,L-lysyl-L-lysyl-;SCHEMBL3796535;L-Lys-(L-Lys)n-L-Lys.xHBr;CHEMBL1229077;DTXSID40948891;CHEBI:160118;WBSCNDJQPKSPII-KKUMJFAQSA-N;AKOS027320373;CS-W009720;FP57749;HY-W009004;FP166353;FP177958;PD167574;NS00126231;G77532;Poly-L-lysine hydrobromide - M.W:1000-5000;Poly-L-lysine hydrobromide - M.W:4000-20000;Poly-L-lysine hydrobromide - M.W:70000-150000;Q27294355;(S)-6-Amino-2-((S)-6-amino-2-((S)-2,6-diaminohexanamido)hexanamido)hexanoicacid;N~2~-{6-Amino-2-[(2,6-diamino-1-hydroxyhexylidene)amino]-1-hydroxyhexylidene}lysine;
Lysyllysyllysine is a synthetic tripeptide composed of three consecutive lysine residues linked via peptide bonds. As a polybasic peptide, it features a high density of primary amine groups, imparting a strong positive charge and significant hydrophilicity under physiological conditions. This molecular arrangement makes it an important model compound for probing the biochemical roles of polylysine motifs in protein interactions, post-translational modifications, and molecular recognition processes. Researchers value its well-defined structure and charge properties for studying fundamental aspects of peptide chemistry, protein engineering, and biophysical interactions involving basic amino acid clusters.
Peptide substrate research: Lysyllysyllysine serves as a valuable substrate in enzymology studies, particularly for investigating the specificity and kinetics of enzymes that target lysine-rich peptide sequences. Its structure allows for the assessment of proteases, lysine-modifying enzymes, and other peptidases that recognize or process basic residues. By providing a controlled and homogeneous substrate, it enables researchers to dissect enzyme mechanisms, evaluate inhibitor efficacy, and understand substrate preferences in a reproducible manner.
Protein-protein interaction modeling: The tripeptide's concentrated positive charge and repetitive lysine motif make it suitable for modeling interactions between polybasic regions of proteins and their cellular partners. It is frequently used in biophysical assays and binding studies to mimic the behavior of lysine-rich domains found in histones, transcription factors, or signaling proteins. Through such experiments, scientists can elucidate the molecular determinants of electrostatic interactions, nucleic acid binding, and the role of basic residues in protein complex formation.
Epigenetics and post-translational modification analysis: Lysyllysyllysine functions as a model compound for studying lysine-targeted post-translational modifications, including acetylation, methylation, and ubiquitination. Its simple structure facilitates the development and optimization of analytical methods such as mass spectrometry, enabling the detection and quantification of modified lysine residues. Researchers also employ it to test the substrate specificity of lysine-modifying enzymes, contributing to a deeper understanding of regulatory mechanisms in chromatin remodeling and gene expression.
Peptide synthesis validation: In the field of synthetic chemistry, this tripeptide is often used as a reference or control during solid-phase peptide synthesis (SPPS) and purification workflows. Its straightforward sequence and basic side chains make it ideal for verifying coupling efficiency, resin compatibility, and deprotection protocols, especially when working with peptides containing multiple basic residues. Analytical evaluation of lysyllysyllysine assists in troubleshooting synthesis challenges and refining methodologies for the production of longer polylysine peptides or other complex sequences.
Biomaterials and surface modification studies: The unique physicochemical properties of this tripeptide, particularly its strong cationic character, enable its use in surface modification and biomaterials research. It is incorporated into coatings and functionalized surfaces to enhance cell adhesion, influence protein adsorption, or modulate electrostatic interactions at interfaces. Such applications are relevant in the design of biosensors, tissue engineering scaffolds, and platforms for studying cell-material interactions, where the presence of basic peptide motifs can significantly impact biological responses.
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