Z-Ile-Ser-OH is a Cbz-protected dipeptide combining hydrophobic isoleucine with polar serine, producing a balanced conformational motif. Researchers employ it to explore steric effects, hydrogen-bonding networks, and polarity-driven structure. The residue pairing supports modeling of mixed hydrophobic-polar interactions.
CAT No: R2312
CAS No:212612-25-4
Synonyms/Alias:Z-Ile-Ser-OH;212612-25-4;NSC333755;NSC-333755;
Z-Ile-Ser-OH, also known as N-carbobenzoxyisoleucylserine, is a synthetic dipeptide featuring a protected N-terminus and a free carboxyl group at the C-terminus. This compound is frequently utilized in peptide synthesis and research due to its stable structure and the presence of both hydrophobic (isoleucine) and polar (serine) residues. The carbobenzoxy (Z) protecting group offers resistance to enzymatic degradation and chemical modifications, making Z-Ile-Ser-OH a valuable intermediate in the stepwise construction of longer peptide sequences. Its versatility and compatibility with various coupling reagents further enhance its appeal in both academic and industrial laboratories focused on peptide chemistry and related fields.
Peptide Synthesis: Z-Ile-Ser-OH serves as a critical building block in the assembly of custom peptides, particularly during solid-phase peptide synthesis (SPPS) and solution-phase synthesis. The N-terminal Z-protection allows for selective deprotection and coupling, facilitating the sequential addition of amino acids without unwanted side reactions. Researchers often incorporate this dipeptide to introduce specific sequence motifs or to study the impact of isoleucine-serine combinations on the structural and functional properties of peptides. Its use supports the efficient generation of peptide libraries, combinatorial chemistry applications, and the design of novel biomolecules for various research purposes.
Enzyme Substrate Studies: As a model substrate, N-carbobenzoxyisoleucylserine is employed to investigate the specificity and catalytic mechanisms of proteolytic enzymes, particularly serine proteases and peptidases. By monitoring the enzymatic cleavage of the dipeptide, scientists can gain insights into substrate recognition, enzyme-substrate interactions, and the influence of N-terminal protection on enzymatic activity. Such studies are instrumental in elucidating the fundamental principles of protein digestion, enzyme engineering, and inhibitor development, contributing to advancements in biochemistry and molecular biology.
Structure-Activity Relationship (SAR) Analysis: The unique combination of isoleucine and serine residues in Z-Ile-Ser-OH makes it an ideal candidate for SAR studies aimed at understanding the correlation between peptide structure and biological activity. Researchers utilize this compound to systematically modify peptide backbones, assess the role of side-chain interactions, and optimize sequences for enhanced stability or functional performance. SAR investigations involving this dipeptide can inform the rational design of bioactive peptides, peptidomimetics, and therapeutic candidates, driving innovation in peptide-based research.
Biophysical and Conformational Studies: Scientists leverage Z-Ile-Ser-OH to explore the conformational preferences and secondary structure formation of short peptides. Its defined sequence and protecting group allow for detailed analysis using techniques such as nuclear magnetic resonance (NMR), circular dichroism (CD) spectroscopy, and X-ray crystallography. These studies help elucidate the folding behavior, hydrogen bonding patterns, and solvent interactions of peptides, providing foundational knowledge for understanding protein structure and dynamics at the molecular level.
Peptide Modification and Functionalization: In chemical biology and materials science, the dipeptide is utilized as a scaffold for further functionalization and derivatization. The presence of a free serine hydroxyl group enables site-specific modifications, such as phosphorylation, glycosylation, or conjugation with fluorescent labels. Researchers exploit these chemical handles to create peptide-based probes, affinity tags, or biomaterials with tailored properties for downstream applications in cell biology, diagnostics, or nanotechnology.
Analytical Method Development: Z-Ile-Ser-OH is frequently used as a standard or model compound in the development and validation of analytical techniques for peptide characterization. Its well-defined structure and reactivity make it suitable for optimizing chromatographic methods, mass spectrometry protocols, and detection assays. Through these applications, the dipeptide supports quality control, method optimization, and the advancement of analytical tools essential for peptide research and development.
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