H-Tyr-Tyr-Tyr-OH contains three aromatic residues that promote π-stacking and spectroscopic detectability. Its repetitive motif supports studies of aromatic clustering and hydrogen bonding. Researchers evaluate conformational preferences under varied conditions. Applications include peptide-material interactions, structural biology, and optical-property investigations.
CAT No: R2458
CAS No:7390-78-5
Synonyms/Alias:H-TYR-TYR-TYR-OH;7390-78-5;(S)-2-((S)-2-((S)-2-Amino-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid;Tyrosyl-tyrosyl-tyrosine;L-Tyrosine, L-tyrosyl-L-tyrosyl-;MFCD00055745;SCHEMBL9419220;L-Tyrosyl-L-tyrosyl-L-tyrosine;CHEMBL1221566;l-tyrosyl-l-tyro-syl-l-tyrosine;L-Tyrosine,L-tyrosyl-L-tyrosyl-;CHEBI:166033;RMRFSFXLFWWAJZ-HJOGWXRNSA-N;CS-W011493;HY-W010777;AS-76422;FT109471;A12806;(2S)-2-[(2S)-2-[(2S)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANOIC ACID;(S)-2-((S)-2-((S)-2-Amino-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanoicacid;
H-Tyr-tyr-tyr-OH is a synthetic tripeptide composed of three tyrosine residues linked in a linear sequence, featuring a free amino group at the N-terminus and a carboxyl group at the C-terminus. As a member of the peptide compound family, it exemplifies the structural and functional diversity that can be achieved through specific amino acid arrangements. The presence of multiple tyrosine units imparts unique physicochemical properties, such as enhanced aromaticity and potential for redox activity, making it a valuable model for studying peptide-protein interactions, enzymatic processes, and signaling pathways. Its defined sequence and accessible functional groups provide an excellent platform for a wide range of biochemical and biophysical investigations.
Peptide structure-function analysis: Researchers frequently employ H-Tyr-tyr-tyr-OH in studies aimed at elucidating the relationship between peptide sequence and biological activity. The trityrosyl motif offers a model system to investigate how aromatic side chains influence peptide conformation, stability, and molecular recognition. By analyzing its behavior in solution or in interaction with proteins, scientists can gain insights into the role of tyrosine clustering in modulating structural motifs such as beta-turns or random coils, which are relevant to both natural and engineered peptides.
Enzyme substrate studies: The tripeptide is highly relevant for enzymology research, particularly as a substrate or inhibitor in assays involving proteases, tyrosine kinases, or tyrosinases. Its repetitive tyrosine sequence provides a suitable scaffold for probing enzyme specificity, catalytic efficiency, and post-translational modification mechanisms such as phosphorylation or oxidation. Use of this peptide in such assays allows for detailed kinetic analyses and mechanistic exploration of enzyme-peptide interactions.
Redox and oxidative stress research: Due to the phenolic side chains of tyrosine residues, H-Tyr-tyr-tyr-OH serves as a model substrate in studies of oxidative modifications and redox biochemistry. It is employed to investigate the susceptibility of tyrosine-rich peptides to reactive oxygen species and to monitor the formation of dityrosine or other oxidative crosslinks. These studies are pertinent in understanding protein aging, oxidative damage, and cellular stress responses, as well as in the development of antioxidant strategies.
Peptide synthesis and analytical method development: The defined sequence and accessible functional groups of this tripeptide make it a valuable standard in peptide synthesis protocols and analytical method validation. It is often utilized to optimize solid-phase peptide synthesis (SPPS) conditions, assess chromatographic separation techniques, and calibrate mass spectrometry or HPLC systems. By serving as a reference compound, it supports the development and quality control of peptide-based research tools and products.
Biomaterials and surface modification research: The aromatic and hydrophilic character of H-Tyr-tyr-tyr-OH makes it suitable for surface modification studies, including the functionalization of biomaterials and nanomaterials. Its ability to interact via π-stacking, hydrogen bonding, and metal coordination enables the design of peptide-based coatings or linkers for biosensors, medical devices, and biointerfaces. Researchers leverage these properties to enhance biocompatibility, promote selective adsorption, or engineer responsive materials for advanced biotechnological applications.
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