[β-Asp5]-Desmopressin contains a β-aspartyl linkage at position 5, introducing a backbone isomerization often associated with degradation. The altered geometry affects hydrogen-bond networks and receptor-contact orientation. Researchers use it as a marker for peptide aging and isomerization pathways. Applications include stability studies, impurity profiling, and peptide-backbone rearrangement research.
CAT No: R2858
Synonyms/Alias:(4R,8S,11S,14S,17S)-4-((S)-2-(((R)-1-((2-amino-2-oxoethyl)amino)-5-((diaminomethylene)amino)-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-11-(3-amino-3-oxopropyl)-14-benzyl-17-(4-hydroxybenzyl)-6,10,13,16,19-pentaoxo-1,2-dithia-5,9,12,15,18-pentaazacyclohenicosane-8-carboxylic acid
[β-Asp5]-Desmopressin is a synthetic peptide analog structurally related to the well-characterized antidiuretic hormone vasopressin, featuring a β-aspartic acid substitution at the fifth position. This modification imparts unique conformational and functional properties to the molecule, making it a valuable tool in peptide research and structure-activity relationship (SAR) studies. As a specialized peptide derivative, [β-Asp5]-Desmopressin serves as a reference compound for evaluating the impact of side-chain isomerization on peptide activity, stability, and receptor interaction. Its distinctive features support a range of advanced biochemical and pharmacological investigations, particularly those focused on peptide design, receptor selectivity, and molecular modeling.
Peptide structure-activity relationship studies: In the context of SAR research, [β-Asp5]-Desmopressin is frequently utilized to dissect the influence of β-aspartic acid incorporation on the biological activity and receptor affinity of desmopressin analogs. By comparing its functional profile to that of native and other modified peptides, researchers can elucidate how specific side-chain alterations affect vasopressin receptor subtype selectivity and downstream signaling. Such comparative analyses are fundamental in guiding the rational design of next-generation peptide ligands with tailored pharmacodynamic properties.
Peptide stability and degradation pathway analysis: The presence of a β-aspartic acid residue in [β-Asp5]-Desmopressin offers a model system for investigating peptide isomerization, degradation mechanisms, and stability under physiological and experimental conditions. Studies employing this analog enable the assessment of spontaneous or enzyme-catalyzed β-Asp formation, which is relevant for understanding peptide aging, shelf-life, and the implications of non-enzymatic post-translational modifications in both synthetic and endogenous peptides. Insights gained from such work inform the development of more stable peptide therapeutics and research reagents.
Receptor binding and affinity profiling: As a modified vasopressin analog, [β-Asp5]-Desmopressin is widely used in receptor binding assays to characterize the specificity, affinity, and kinetic parameters of peptide-receptor interactions. Employing this compound in competitive binding experiments with V1a, V1b, and V2 vasopressin receptors allows for the detailed mapping of ligand recognition sites and the identification of structural determinants that govern selectivity. These data are instrumental in advancing the understanding of G protein-coupled receptor (GPCR) pharmacology and in the design of selective receptor modulators.
Analytical method development and peptide quantification: The distinct physicochemical properties of [β-Asp5]-Desmopressin make it a useful internal standard or calibration reference in the development of analytical methods for peptide identification and quantification. Its unique mass spectrometric and chromatographic signatures facilitate the validation of LC-MS/MS or HPLC protocols, ensuring accurate detection and measurement of peptide species in complex biological or synthetic mixtures. Such applications are critical for quality control, pharmacokinetic studies, and the monitoring of peptide integrity in research and industrial settings.
Peptide synthesis and process optimization: The synthesis of [β-Asp5]-Desmopressin provides a benchmark for evaluating strategies to control aspartic acid isomerization and minimize side-product formation during solid-phase peptide synthesis (SPPS). Researchers and process chemists utilize this analog to optimize coupling conditions, resin selection, and deprotection protocols, thereby improving the yield and purity of peptides containing aspartic acid residues. The insights derived from these studies contribute to more efficient manufacturing workflows and higher-quality peptide products for research applications.
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