Dansyl-Tyr-Val-Gly contains a dansyl fluorophore tethered to a short tripeptide, enabling polarity-sensitive fluorescence. Tyrosine contributes aromatic stacking and hydrogen bonding, while valine and glycine tune flexibility. Researchers apply it to microenvironment sensing and protease-substrate studies. Applications include fluorescence assays, peptide-labeling research, and binding-interface probing.
CAT No: R2391
CAS No:113527-49-4
Synonyms/Alias:DANSYL-TYR-VAL-GLY;113527-49-4;2-[[(2S)-2-[[(2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]acetic acid;Dansyl-Tyr-Val-Gly-OH trifluoroacetate salt;Dansyl-Y-V-G;CHEMBL514254;SCHEMBL9419212;FD73670;DA-52306;FD111002;HY-138126;CS-0145367;2-((S)-2-((S)-2-(5-(dimethylamino)naphthalene-1-sulfonamido)-3-(4-hydroxyphenyl)propanamido)-3-methylbutanamido)acetic acid;
Dansyl-tyr-val-gly is a synthetic tripeptide featuring an N-terminal dansyl (5-dimethylaminonaphthalene-1-sulfonyl) group, which imparts strong fluorescent properties to the molecule. As a labeled peptide, it serves as a versatile probe in biochemical research, enabling sensitive detection and quantification of peptide interactions and enzymatic processes. The combination of tyrosine, valine, and glycine residues provides a structurally relevant motif for investigating protease specificity, substrate recognition, and peptide transport mechanisms. Its fluorescent tag not only facilitates real-time monitoring in complex biological systems but also enhances the utility of the peptide in a variety of analytical and mechanistic studies.
Fluorescence-based enzymatic assays: Dansyl-tyr-val-gly is widely employed as a substrate in fluorescence-based assays for protease activity profiling. The presence of the dansyl group allows for the sensitive detection of peptide cleavage events, as enzymatic hydrolysis typically results in measurable changes in fluorescence intensity. Researchers utilize this property to assess the specificity, kinetics, and inhibition of various proteolytic enzymes, including serine and cysteine proteases, under physiologically relevant conditions. The peptide's sequence can be tailored to match the substrate preferences of target enzymes, facilitating detailed studies of enzymatic mechanisms and inhibitor screening.
Peptide transport and uptake studies: The fluorescent labeling of this tripeptide makes it highly suitable for investigating cellular uptake, peptide transport mechanisms, and subcellular localization. By tracking the intrinsic fluorescence of the dansyl group, scientists can monitor the internalization of the peptide by different cell types, quantify transport efficiency, and elucidate the roles of specific peptide transporters. Such studies are crucial for understanding nutrient absorption, drug delivery strategies, and the functional dynamics of membrane transport proteins.
Protein-peptide interaction analysis: Dansyl-tyr-val-gly serves as an effective probe for characterizing protein-peptide interactions in solution and at biological interfaces. The fluorescence properties of the dansyl moiety can be exploited in binding assays, such as fluorescence polarization or Förster resonance energy transfer (FRET), to determine binding affinities, stoichiometry, and conformational changes upon complex formation. These applications are instrumental in mapping interaction sites, validating molecular recognition models, and supporting the rational design of peptide-based modulators.
Analytical method development: The unique spectral characteristics of the dansyl group enable the use of this labeled tripeptide as a calibration standard or tracer in chromatographic and electrophoretic techniques. Researchers integrate it into high-performance liquid chromatography (HPLC), capillary electrophoresis, and mass spectrometry workflows to optimize detection sensitivity, validate separation protocols, and standardize quantification methods for peptide analysis. Its well-defined structure and robust fluorescence make it a reliable reference compound in method validation and quality control.
Peptide synthesis and labeling optimization: In peptide chemistry, dansyl-tyr-val-gly is utilized as a model system to evaluate and refine strategies for peptide labeling and post-synthetic modifications. The incorporation of a fluorescent tag at the N-terminus provides insights into labeling efficiency, stability, and the impact of chemical modifications on peptide properties. Such studies inform the development of new fluorescent probes, advance solid-phase peptide synthesis techniques, and support the customization of labeled peptides for specialized research applications.
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