(Arg8, des-Gly-NH2⁹)-Vasopressin presents a modified cyclic peptide architecture used to evaluate residue-specific effects on conformation. Substitutions alter charge distribution and receptor-binding determinants. Researchers explore its structural rigidity and solvent-dependent dynamics. Uses include ligand analog design, motif-function mapping, and conformational analysis.
CAT No: R2644
CAS No:37552-33-3
Synonyms/Alias:(arg8,des-Gly-NH29)-vasopressin;DGAVP;37552-33-3;HN9TZR2O9V;(2S)-2-[[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid;[Deglycinamide9, Arginine8]-Vasopressin;Org 5667;DEAVP;9-Des-glynh2-argipressin;9-Deglycinamide-argipressin;(Arg8,de-Gly9)-vasopressin;Arginine vasopression-(1-8);Argipressin, des-glynh2(9)-;Argipressin, desglycinamide(9)-;Argipressin, de-glycinamide(9)-;MFCD00076741;(Deglycinamide9,arginine8)-vasopressin;8-Arginine-9-deglycinamide-vasopressin;Arginine vasopressin, des-glynh2(9)-;(Desglycinamide9-arginine8)-vasopressin;8-Arginine-9-desglycinamide vasopressin;8-Arg-9-des-gly-vasopressin dicitrate salt;UNII-HN9TZR2O9V;Vasopressin, 8-L-arginine-9-deglycinamide-;1-8-Vasopressin, 8-L-arginine-;ORG-5667;DESGLYCINAMIDE ARGININE VASOPRESSIN;HY-106102;CS-0024862;(Arg8,des-Gly-NH29)-Vasopressin (H-L-Cys(1)-L-Tyr-L-Phe-L-Gln-L-Asn-L-Cys(1)-L-Pro-L-Arg-OH);
(arg8,des-Gly-NH29)-vasopressin is a synthetic peptide analog of the naturally occurring antidiuretic hormone vasopressin, engineered with specific amino acid substitutions to alter its biological profile. As a modified nonapeptide, it features the replacement of arginine at position 8 and the removal of glycine at position 9, with an amidated C-terminus. These structural modifications render it a valuable molecular tool for dissecting the structure-activity relationships of vasopressin and its receptor interactions. The compound is widely employed in biochemical and physiological research to investigate the mechanisms underlying peptide hormone signaling, receptor specificity, and the functional consequences of targeted peptide alterations.
Receptor Binding Studies: In receptor pharmacology, (arg8,des-Gly-NH29)-vasopressin serves as a reference ligand for probing the binding affinity and selectivity of vasopressin receptors, particularly within the V1 and V2 subtypes. Its altered peptide backbone allows researchers to delineate the contributions of specific residues to receptor recognition and activation, advancing the understanding of ligand-receptor interactions at the molecular level. This analog is especially useful for comparative studies involving native vasopressin, oxytocin, and other related peptides, thereby facilitating the mapping of critical contact points within receptor binding domains.
Signal Transduction Research: The compound is frequently utilized in studies focused on intracellular signaling cascades initiated by vasopressin receptor engagement. By employing (arg8,des-Gly-NH29)-vasopressin in cell-based assays or membrane preparations, scientists can monitor downstream events such as cyclic AMP accumulation, phosphoinositide turnover, or calcium mobilization. These investigations help clarify how specific peptide modifications influence G protein-coupled receptor activation and subsequent cellular responses, supporting efforts to unravel the complexities of hormone-mediated signaling networks.
Peptide Structure-Activity Relationship (SAR) Analysis: As a structurally defined analog, (arg8,des-Gly-NH29)-vasopressin is instrumental in systematic SAR studies. Researchers use it to assess how targeted changes in peptide sequence affect biological function, stability, and receptor interaction profiles. Such experiments provide key insights into the determinants of peptide hormone efficacy and selectivity, informing the rational design of novel analogs with tailored pharmacological properties for research applications.
Peptide Synthesis and Analytical Method Development: The unique sequence of this analog makes it a valuable standard in peptide synthesis optimization and analytical method validation. Laboratories engaged in solid-phase peptide synthesis (SPPS) or chromatographic analysis employ (arg8,des-Gly-NH29)-vasopressin to benchmark synthetic yields, evaluate purification strategies, and calibrate analytical instruments. Its well-characterized physicochemical properties aid in troubleshooting and refining peptide production workflows, contributing to improved reproducibility and quality control in peptide research.
Neuroendocrine System Investigations: In neurobiology and endocrinology, (arg8,des-Gly-NH29)-vasopressin is applied to dissect the functional roles of vasopressinergic signaling in neural and endocrine tissues. By selectively modulating receptor activity with this analog, researchers can explore the physiological relevance of peptide hormone variants, analyze feedback mechanisms, and investigate the integration of neuropeptide signals within complex regulatory networks. These studies enhance the understanding of hormone action in diverse biological systems, supporting the discovery of new targets for basic research and translational inquiry.
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