Z-Tyr-Tyr-OH links two aromatic residues under a benzyloxycarbonyl protecting group, aiding synthetic control and structural studies. The dipeptide supports analysis of π-stacking and spectroscopic properties. Researchers examine its coupling efficiency in peptide-assembly workflows. Applications include synthetic chemistry, motif construction, and aromatic-interaction modeling.
CAT No: R2490
CAS No:10417-83-1
Synonyms/Alias:Z-Tyr-Tyr-OH;10417-83-1;(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid;AKOS024432242;FT111525;CARBOBENZYLOXY-L-TYROSYL-L-TYROSINE;(S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanoic acid;(S)-2-((S)-2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-(4-hydroxyphenyl)propanoic acid;
Z-Tyr-Tyr-OH, also known as N-carbobenzoxy-L-tyrosyl-L-tyrosine, is a synthetic dipeptide composed of two tyrosine residues with an N-terminal benzyloxycarbonyl (Z) protective group. As a member of the protected peptide category, this compound is widely utilized in peptide chemistry and biochemical research due to its stability, defined sequence, and functionalizable side chains. The presence of the Z-group safeguards the N-terminus during sequential peptide assembly, while the dual tyrosine units provide aromatic side chains that can participate in hydrogen bonding, π-π interactions, and enzymatic recognition. Its design makes it particularly valuable for researchers seeking to study peptide structure, function, and synthesis methodologies in a controlled and reproducible manner.
Peptide synthesis: In solid-phase and solution-phase peptide synthesis, Z-Tyr-Tyr-OH serves as a key protected dipeptide building block. The N-terminal benzyloxycarbonyl group enables selective incorporation into growing peptide chains while preventing unwanted side reactions at the amino terminus. This allows chemists to efficiently construct longer peptides with precise sequence fidelity, especially when incorporating tyrosine-rich motifs. The protected dipeptide format simplifies coupling strategies, reduces the need for repetitive protection and deprotection steps, and enhances overall synthetic efficiency in research and development settings.
Peptide structure-function studies: The dipeptide is frequently employed in investigations aimed at elucidating the structural and functional roles of tyrosine residues within peptides and proteins. Its defined sequence and protected termini facilitate the study of aromatic interactions, hydrogen bonding patterns, and conformational preferences in short peptide models. Researchers can use it to probe the influence of tyrosine pairing on peptide folding, stability, and intermolecular associations, generating insights relevant to protein engineering and biomolecular design.
Enzymatic specificity assays: Z-Tyr-Tyr-OH is a valuable substrate or reference compound in enzymology studies focused on protease specificity and activity. The protected N-terminus enables selective investigation of C-terminal processing events and provides a model for assessing the substrate preferences of exopeptidases and endopeptidases. By monitoring the enzymatic cleavage or modification of this dipeptide, researchers can characterize enzyme kinetics, substrate selectivity, and mechanistic aspects of peptide bond hydrolysis.
Analytical method development: In analytical chemistry, the compound is used as a standard or calibration reference for chromatographic and spectrometric techniques targeting peptides. Its defined composition and physicochemical properties make it suitable for optimizing separation protocols, validating detection methods, and establishing quantitative assays for peptide analysis. The aromatic tyrosine side chains also permit UV absorbance-based quantification, further supporting its use in method validation and quality control processes.
Peptide modification research: The presence of two tyrosine residues renders Z-Tyr-Tyr-OH an ideal model for exploring site-specific chemical modifications such as phosphorylation, nitration, or cross-linking. Researchers utilize it to develop and refine protocols for introducing post-translational modifications or for generating peptide conjugates with tailored functionalities. These studies are instrumental in advancing understanding of peptide reactivity, developing new bioconjugation strategies, and supporting the design of functionalized biomolecules for downstream applications.
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