Trp-Arg pairs an aromatic indole-containing residue with a strongly basic arginine, enabling π-cation interaction studies. Researchers examine its folding, hydrogen bonding, and solvent behavior. The dipeptide aids in modeling membrane-binding and nucleic-acid interactions. Applications include peptide-design research, spectroscopic studies, and interaction mapping.
CAT No: R2360
CAS No:88831-09-8
Synonyms/Alias:Trp-Arg;88831-09-8;L-Arginine, L-tryptophyl-;tryptophanyl-arginine;L-Tryptophan-L-arginine;H-Trp-Arg-OH;CHEMBL477417;CHEBI:74866;(S)-2-((S)-2-Amino-3-(1H-indol-3-yl)propanamido)-5-guanidinopentanoic acid;(2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid;Tryptophyl-Arginine;L-tryptophyl-L-arginine;L-Trp-L-Arg;L-Tryptophanyl-L-arginine;H-Trp-Arg-OH.2 HCl;SCHEMBL4947728;(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-5-carbamimidamidopentanoic acid;HY-P4635;WR;BDBM50266680;FT108193;CS-0655433;Q27144975;
Trp-Arg, also known as Tryptophan-Arginine, is a synthetic dipeptide composed of the essential amino acids tryptophan and arginine linked via a peptide bond. As a member of the peptide compound category, Trp-Arg offers unique physicochemical and biochemical properties derived from the combination of its constituent residues. The indole ring of tryptophan imparts aromatic character and potential for π-π interactions, while the guanidinium group of arginine contributes positive charge and hydrogen bonding capacity. These attributes make Trp-Arg a valuable tool for researchers investigating peptide structure-function relationships, protein interactions, and cellular signaling mechanisms. Its defined sequence and manageable size allow for precise experimental manipulation, supporting a wide range of scientific inquiries in biochemistry, molecular biology, and related disciplines.
Peptide structure-function analysis: Trp-Arg is frequently utilized in studies aimed at elucidating the relationship between peptide sequence and biological activity. The presence of tryptophan provides an intrinsic fluorophore, enabling direct monitoring of peptide behavior using fluorescence-based techniques. Researchers leverage this property to assess conformational changes, binding interactions, and environmental sensitivity, offering insight into how the dipeptide's sequence influences its structural dynamics and functional roles in model systems.
Protein-peptide interaction studies: The dipeptide serves as a model ligand for characterizing protein-peptide recognition events, particularly those involving aromatic and basic side chains. Its ability to engage in both hydrophobic stacking and electrostatic interactions makes it a useful probe for mapping binding sites within enzymes, receptors, or antibody paratopes. Employing Trp-Arg in surface plasmon resonance, isothermal titration calorimetry, or NMR spectroscopy experiments aids in defining the molecular determinants of specificity and affinity in protein-ligand complexes.
Cellular uptake and transport research: Due to its moderate size and distinct physicochemical features, Trp-Arg is often employed to investigate mechanisms of peptide transport across biological membranes. Studies using this dipeptide help clarify the substrate specificity of peptide transporters such as PEPT1 and PEPT2, as well as the influence of charge and hydrophobicity on cellular uptake efficiency. These insights are particularly valuable for the rational design of peptide-based delivery systems and for understanding nutrient absorption processes.
Peptide synthesis optimization: Trp-Arg is commonly used as a model substrate in the development and validation of peptide synthesis methodologies. Its sequence presents both synthetic challenges and opportunities, such as the potential for side-chain interactions or racemization. By monitoring the coupling efficiency and purity of this dipeptide, chemists can optimize reaction conditions, evaluate protecting group strategies, and benchmark new synthetic protocols. This application is essential for advancing solid-phase and solution-phase peptide synthesis technologies.
Analytical standard in chromatography: The well-defined structure and distinctive spectroscopic characteristics of Trp-Arg make it an excellent reference compound in peptide analysis workflows. It is frequently used as a calibration standard or system suitability marker in high-performance liquid chromatography (HPLC) and mass spectrometry. Utilizing this dipeptide enables accurate assessment of chromatographic resolution, retention time reproducibility, and detector response, supporting quality control in peptide characterization and quantification procedures.
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