Ac-DCit6-Cetrorelix features an acetylated N-terminus and a didehydrocitrulline modification at position 6, altering charge and local geometry. Such changes affect hydrogen bonding, flexibility, and receptor-interaction profiles. Researchers compare its structural ensemble against native cetrorelix. Applications include analog-optimization work, conformational analysis, and receptor-binding mechanism studies.
CAT No: Z10-101-211
CAS No:1631741-33-7
Synonyms/Alias:(S)-1-(((R)-2-((S)-2-((S)-2-((R)-2-((R)-2-((R)-2-acetamido-3-(naphthalen-2-yl)propanamido)-3-(4-chlorophenyl)propanamido)-3-(pyridin-3-yl)propanamido)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido)-5-(3-acetylureido)pentanoyl)-L-leucyl-L-arginyl)-N-((R)-1-amino-1-oxopropan-2-yl)pyrrolidine-2-carboxamide; Ac-D-2-Nal-D-Phe (4-Cl)-D-3-Pal-Ser-Tyr-D-Cit (Ac)-Leu-Arg-Pro-D-Ala-NH2; (S)-1-(((R)-2-((S)-2-((S)-2-((R)-2-((R)-2-((R)-2-acetamido-3-(naphthalen-2-yl)propanamido)-3-(4-chlorophenyl)propanamido)-3-(pyridin-3-yl)propanamido)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido)-5-(3-acetylureido)pentanoyl)-L-leucyl-L-arginyl)-N-((R)-1-amino-1-oxopropan-2-yl)pyrrolidine-2-carboxamide;
Ac-DCit6-Cetrorelix is a synthetic peptide analog structurally derived from the well-characterized gonadotropin-releasing hormone (GnRH) antagonist cetrorelix, featuring an N-terminal acetylation and the incorporation of six D-citrulline residues. As a member of the peptide compound class, it is designed to modulate peptide-receptor interactions and exhibit enhanced stability profiles compared to its parent molecule. Its unique sequence modifications offer valuable tools for researchers investigating structure-activity relationships, receptor binding dynamics, and peptide pharmacology in the context of reproductive hormone regulation and related signaling pathways. The tailored structural features of Ac-DCit6-Cetrorelix make it a highly relevant molecule for advanced peptide research and biochemical studies seeking to probe the functional consequences of amino acid substitutions within bioactive peptides.
Peptide receptor interaction studies: The modified sequence of Ac-DCit6-Cetrorelix enables detailed analysis of ligand-receptor binding mechanisms, particularly regarding the GnRH receptor and its analogs. Researchers utilize this peptide to assess the impact of D-citrulline substitutions on binding affinity, selectivity, and antagonistic potency. Such investigations elucidate the molecular determinants governing peptide-receptor specificity and inform the rational design of next-generation GnRH antagonists with altered biological profiles.
Structure-activity relationship (SAR) research: Incorporation of D-citrulline residues in Ac-DCit6-Cetrorelix provides a platform for systematic SAR studies. By comparing the biological and physicochemical properties of this analog to those of native cetrorelix or other variants, scientists gain insight into the influence of side-chain modifications on peptide conformation, stability, and functional activity. These studies are essential for understanding how specific sequence alterations modulate peptide behavior and for guiding the optimization of peptide therapeutics or research probes.
Peptide stability and degradation assays: The presence of non-canonical D-amino acids in Ac-DCit6-Cetrorelix renders it a valuable reference compound for evaluating peptide stability in biological matrices. It is frequently employed in enzymatic degradation assays to quantify resistance to proteolytic cleavage, which is critical for developing peptides with improved in vitro and in vivo longevity. Such applications are central to peptide drug discovery, as enhanced stability directly impacts pharmacokinetic properties and overall research utility.
Analytical method development: Laboratories engaged in bioanalytical chemistry and peptide quantification employ Ac-DCit6-Cetrorelix as a model substrate for validating chromatographic, spectrometric, and immunochemical detection methods. Its defined structure and unique sequence features facilitate the optimization of analytical protocols, enabling accurate measurement of peptide concentrations in complex biological samples. This supports robust assay development for both research and quality control environments.
Peptide synthesis optimization: Synthetic chemists leverage Ac-DCit6-Cetrorelix to refine solid-phase peptide synthesis (SPPS) strategies, particularly when incorporating multiple D-amino acids or non-standard residues. Its assembly provides a challenging yet informative template for troubleshooting coupling efficiency, sequence fidelity, and purification processes. Insights gained from synthesizing and characterizing this peptide contribute to improved methodologies for producing structurally complex and functionally diverse peptide libraries, advancing the field of peptide engineering and research tool development.
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