Z-Tyr-Ser-OH is a protected dipeptide featuring a Cbz-protected tyrosine and an unprotected serine. Researchers use it to study hydrogen bonding, aromatic interactions, and β-turn formation. The protection scheme allows controlled synthetic manipulation. Its simplicity supports targeted structural analysis.
CAT No: R2308
CAS No:20448-71-9
Synonyms/Alias:Z-Tyr-Ser-OH;20448-71-9;L-Serine, N-[N-[(phenylmethoxy)carbonyl]-L-tyrosyl]- (9CI);FT111524;(2S)-3-hydroxy-2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid;(S)-2-((S)-2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-hydroxypropanoic acid;
Z-Tyr-Ser-OH is a synthetic dipeptide composed of N-benzyloxycarbonyl-tyrosine (Z-Tyr) and serine (Ser), featuring a protected N-terminus to facilitate controlled peptide synthesis and structural studies. As a member of the peptide compound category, Z-Tyr-Ser-OH serves as a valuable intermediate in the assembly of longer peptide chains and as a model substrate for enzymatic and biochemical investigations. Its defined sequence, incorporation of a benzyloxycarbonyl (Z) protective group, and presence of both aromatic and hydroxyl functionalities make it especially relevant for research in peptide chemistry, enzymology, and structure-function analyses.
Peptide Synthesis: Z-Tyr-Ser-OH is widely utilized as a building block in solid-phase and solution-phase peptide synthesis protocols. The N-terminal Z-protection ensures selective reactivity by preventing undesired side reactions, allowing for precise elongation of peptide chains. Researchers leverage this dipeptide to streamline the assembly of complex oligopeptides, particularly when incorporating tyrosine and serine residues in defined positions is critical for mimicking natural sequences or designing functional analogs.
Enzymology Studies: As a model substrate, the dipeptide is frequently employed in studies of protease specificity and mechanism. Its sequence enables detailed investigation of enzyme-substrate interactions, particularly for serine proteases and tyrosine-targeting enzymes. By monitoring the cleavage or modification of Z-Tyr-Ser-OH, researchers can elucidate catalytic preferences, substrate recognition motifs, and inhibitor efficacy, providing insights that inform both basic enzymology and inhibitor development.
Structure-Activity Relationship (SAR) Research: The well-defined structure of Z-Tyr-Ser-OH makes it an effective probe in structure-activity relationship studies. By systematically varying protective groups or adjacent amino acids, scientists can assess how modifications influence peptide conformation, stability, and biological interactions. Such studies are essential for optimizing peptide-based ligands, developing novel biomimetics, or understanding the physicochemical determinants of peptide function.
Analytical Method Development: In the context of analytical chemistry, this dipeptide serves as a standard or calibration compound for chromatographic and spectroscopic techniques. Its unique combination of aromatic and polar side chains provides characteristic retention and detection profiles, aiding in the validation of peptide separation methods and the quantification of related species in complex mixtures. The reproducible behavior of Z-Tyr-Ser-OH supports method development for both research and quality control laboratories.
Peptide Functional Studies: Z-Tyr-Ser-OH is also valuable in exploring the functional roles of short peptide motifs in biochemical pathways. By incorporating this dipeptide into synthetic peptides or conjugates, researchers can dissect the contribution of tyrosine and serine residues to molecular recognition, phosphorylation events, or intermolecular interactions. Such studies enhance the understanding of sequence-dependent peptide behavior and support the rational design of functional biomolecules for research applications.
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