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 is a synthetic dipeptide composed of N-carbobenzoxy-L-isoleucyl-L-serine, featuring a protected N-terminus and a free carboxyl group. As a member of the peptide compound category, it serves as a valuable intermediate in peptide chemistry, with particular relevance for researchers engaged in the synthesis and study of oligopeptides and protein fragments. The incorporation of the Z (benzyloxycarbonyl) protecting group on the isoleucine residue enhances its utility in solid-phase and solution-phase peptide synthesis, facilitating selective coupling reactions and minimizing undesired side reactions. Its structural attributes make it a versatile building block for the development of novel peptide sequences and the investigation of peptide-based biological processes.
Peptide Synthesis: Z-Ile-Ser-OH is widely employed as a protected dipeptide intermediate in both solid-phase and solution-phase peptide synthesis protocols. The presence of the Z-protecting group on the N-terminus of isoleucine allows for orthogonal deprotection strategies, enabling stepwise elongation of peptide chains with high fidelity. This compound is particularly useful for constructing peptides containing the isoleucine-serine motif, which is commonly found in biologically active peptides and proteins. Its use streamlines the assembly of complex peptide sequences by reducing the risk of racemization and facilitating efficient coupling reactions.
Peptide Structure-Activity Relationship Studies: In biochemical research, protected dipeptides such as Z-Ile-Ser-OH are instrumental for investigating the structure-activity relationships (SAR) of peptide-based molecules. By incorporating this dipeptide into model peptides or analogs, researchers can systematically explore how the isoleucine-serine sequence contributes to biological activity, receptor binding, or conformational properties. Such studies provide critical insights into the functional roles of specific amino acid motifs within larger peptide frameworks.
Enzymatic Specificity Assays: The compound is also utilized as a substrate or reference standard in enzymatic assays designed to characterize protease specificity and activity. Its defined structure allows researchers to assess the cleavage preferences of serine proteases, exopeptidases, or other peptide-modifying enzymes. By monitoring the hydrolysis or transformation of the dipeptide, scientists can elucidate enzyme-substrate interactions and develop selective inhibitors or probes for biochemical investigations.
Peptide Modification and Derivatization: Z-Ile-Ser-OH serves as a precursor for the synthesis of modified peptides, including those bearing labeled, functionalized, or otherwise derivatized side chains. The protected nature of the compound permits selective chemical modifications at positions not masked by the Z-group, enabling the introduction of reporter groups, affinity tags, or other functional moieties. Such derivatized peptides are valuable tools for studying protein-protein interactions, cellular uptake, or localization in advanced biochemical assays.
Analytical Method Development: In the context of analytical chemistry, this dipeptide is employed as a standard or calibration compound for high-performance liquid chromatography (HPLC), mass spectrometry, and related techniques. Its well-defined physicochemical properties make it suitable for optimizing separation protocols, validating detection methods, and quantifying peptide species in complex mixtures. The availability of Z-Ile-Ser-OH thus supports rigorous quality control and method validation in peptide research and development laboratories.
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