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-carbobenzyloxy-L-tyrosyl-L-tyrosine, is a synthetic dipeptide featuring two tyrosine residues protected by a benzyloxycarbonyl (Z) group at the N-terminus. This compound is widely recognized for its stability, ease of handling, and compatibility with various peptide synthesis protocols. Its unique structure, incorporating the aromatic side chains of tyrosine, renders it highly valuable for research applications that demand precise control over peptide assembly and modification. The presence of the Z-protecting group not only shields the amino functionality during synthesis but also facilitates selective deprotection strategies, making Z-Tyr-Tyr-OH an indispensable intermediate in the field of peptide chemistry.
Peptide Synthesis: In solid-phase and solution-phase peptide synthesis, Z-Tyr-Tyr-OH serves as a crucial building block for the stepwise elongation of peptide chains. Researchers frequently utilize this dipeptide as a protected fragment to streamline the assembly of larger, more complex peptides, especially those containing sequential tyrosine residues. Its compatibility with standard coupling reagents and deprotection methods ensures high yields and minimal side reactions, supporting the efficient generation of custom peptides for biochemical investigations.
Enzyme Substrate Studies: As a model substrate, N-carbobenzyloxy-L-tyrosyl-L-tyrosine is employed in enzymology to probe the specificity and catalytic mechanisms of proteases and peptidases. By incorporating this dipeptide into enzyme assays, scientists can monitor cleavage events, analyze kinetic parameters, and elucidate substrate preferences. The aromatic side chains of tyrosine further enable spectroscopic detection, enhancing the sensitivity of enzymatic studies and facilitating the development of novel enzyme inhibitors.
Structure-Activity Relationship (SAR) Research: In medicinal chemistry and drug discovery, Z-Tyr-Tyr-OH is instrumental in investigating the structure-activity relationships of peptide-based therapeutics. By systematically modifying the dipeptide framework or incorporating it into larger bioactive sequences, researchers can assess the impact of tyrosine residues on biological activity, receptor binding, and cellular uptake. These insights inform the rational design of peptides with enhanced pharmacological properties and targeted biological functions.
Bioconjugation and Labeling: The functional groups present in N-carbobenzyloxy-L-tyrosyl-L-tyrosine make it amenable to various bioconjugation strategies. Scientists often exploit the phenolic hydroxyl groups of tyrosine for site-specific labeling with fluorescent dyes, affinity tags, or other probes. Such modifications enable the generation of labeled peptides for imaging, tracking, and interaction studies, expanding the toolkit available for molecular biology and analytical applications.
Material Science and Biomaterials: In the context of materials research, Z-Tyr-Tyr-OH is utilized as a precursor for the synthesis of peptide-based hydrogels, nanomaterials, and biomimetic coatings. Its ability to participate in self-assembly processes and crosslinking reactions, driven by the aromatic interactions and hydrogen bonding capabilities of tyrosine, facilitates the creation of novel materials with tunable mechanical, optical, and bioactive properties. These materials find use in tissue engineering, drug delivery, and biosensing platforms, highlighting the versatility of this dipeptide in interdisciplinary research.
Chemical Biology Tool Development: The application of N-carbobenzyloxy-L-tyrosyl-L-tyrosine extends to the development of innovative chemical biology tools. By integrating this dipeptide into peptide libraries, affinity matrices, or combinatorial screening platforms, researchers can dissect protein-protein interactions, map post-translational modifications, and identify new molecular targets. Its structural features and chemical reactivity support the exploration of complex biological systems, underscoring its value in advancing both fundamental and applied scientific research.
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