Oxytocin, Asp(5)- replaces a native residue at position five with aspartate, shifting local charge and hydrogen-bonding capacity within the cyclic ring. The substitution modulates backbone geometry and side-chain interactions important for receptor recognition. Researchers compare its solution structure and binding behavior to native oxytocin. Applications include cyclic-peptide engineering, SAR exploration, and motif-function mapping.
CAT No: R2374
CAS No:65907-78-0
Synonyms/Alias:5-Asp-oxytocin;65907-78-0;Oxytocin, aspartic acid(5)-;Oxytocin, asp(5)-;Oxytocin, 5-L-aspartic acid-;2-[(4R,7S,10S,16S,19R)-19-amino-4-[(2S)-2-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-7-yl]acetic acid;[Asp5]-Oxytocin;SCHEMBL15511486;G18218;
Oxytocin, asp(5)- is a synthetic peptide analog distinguished by the substitution of aspartic acid at the fifth position within the oxytocin sequence. As a variant of the naturally occurring neuropeptide oxytocin, this modified peptide is of significant interest to researchers investigating structure-activity relationships, receptor binding dynamics, and the nuanced roles of peptide hormones in cellular signaling. Its unique amino acid substitution provides a valuable tool for dissecting the molecular determinants of oxytocin receptor interaction, downstream signaling pathways, and the broader implications of peptide modification in biochemical and pharmacological research.
Receptor Binding Studies: The aspartic acid substitution in oxytocin, asp(5)- enables detailed investigation into the specificity and affinity of peptide-receptor interactions. Researchers utilize this analog to probe the structural features critical for oxytocin receptor engagement, helping to elucidate the influence of position 5 on ligand recognition and receptor activation. Such studies are essential for understanding how subtle sequence variations affect receptor selectivity, signaling efficacy, and the potential development of receptor subtype-selective ligands.
Structure-Activity Relationship (SAR) Analysis: In peptide research, analogs like oxytocin, asp(5)- are instrumental for mapping the correlation between primary sequence modifications and biological activity. By comparing the functional properties of this analog to native oxytocin and other derivatives, investigators can identify key residues required for activity, stability, and bioavailability. SAR studies using this peptide facilitate rational design of new analogs with optimized functional profiles for diverse experimental objectives.
Peptide Synthesis and Analytical Method Development: As a structurally defined peptide analog, oxytocin, asp(5)- serves as a reference standard in the development and validation of analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry. Its well-characterized sequence and predictable physicochemical properties make it suitable for calibrating instrumentation, optimizing peptide purification protocols, and verifying synthetic methodologies in peptide chemistry laboratories.
Cell Signaling Pathway Investigation: The impact of sequence modifications on downstream signaling cascades is a central question in peptide hormone research. Oxytocin, asp(5)- allows for the comparative analysis of intracellular responses following receptor activation, including second messenger production, phosphorylation events, and gene expression changes. Such studies provide insights into the functional consequences of peptide engineering and contribute to a deeper understanding of cell signaling modulation by peptide ligands.
Peptide-Protein Interaction Studies: The incorporation of aspartic acid at position 5 in this analog offers a unique probe for exploring peptide-protein interactions beyond the canonical receptor context. Researchers employ oxytocin, asp(5)- to examine binding affinities and interaction profiles with plasma proteins, enzymes, and other cellular components. These investigations inform on the pharmacokinetic behavior, metabolic stability, and potential off-target effects of peptide analogs, supporting the design of peptides with tailored in vitro and in vivo properties.
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