(D-His2)-Leuprolide Trifluoroacetic Acid Salt features a stereochemical substitution at position two, modifying receptor-contact geometry and backbone folding. The peptide's aromatic and charged residues support structural studies of ligand dynamics. Researchers employ it to investigate conformation-driven recognition and helix formation. Its TFA form improves solubility and handling.
CAT No: R2262
CAS No:112642-11-2
Synonyms/Alias:12642-11-2;(D-His2)-Leuprolide Trifluoroacetic Acid Salt;(Des-Gly10,D-His2,D-Leu6,Pro-NHEt9)-LHRH;MFCD02264520;D-HIS-LEUPROLIDE;TN3XE824EM;FD109240;(Des-Gly10,D-His2,D-Leu6,Pro-NHEt 9)-LHRH;Pyr-D-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt; pE-(dH)WSY(dL)LRP-NHEt;5-OXO-L-PROLYL-D-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TYROSYL-D-LEUCYL-L-LEUCYL-L-ARGINYL-N-ETHYL-L-PROLINAMIDE; (S)-1-((3R,6S,9S,12S,15R,18S,21S)-3-((1H-imidazol-5-yl)methyl)-6-((1H-indol-3-yl)methyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-15,18-diisobutyl-1,4,7,10,13,16,19-heptaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-N-ethylpyrrolidine-2-carboxamide; (D-His2)-Leuprolide
(D-His2)-Leuprolide Trifluoroacetic Acid Salt is a synthetic peptide analog derived from the well-known gonadotropin-releasing hormone (GnRH) agonist, leuprolide, in which the second amino acid residue is substituted with D-histidine. This structural modification imparts unique biochemical properties, influencing receptor binding affinity, metabolic stability, and resistance to enzymatic degradation. As a trifluoroacetic acid salt, the compound is provided in a highly soluble and stable form, facilitating its integration into a variety of peptide research workflows. Its sequence-specific alteration and well-defined physicochemical characteristics make it a valuable tool for investigating structure-activity relationships and functional modulation within the GnRH signaling pathway.
Peptide structure-activity relationship studies: (D-His2)-Leuprolide Trifluoroacetic Acid Salt serves as a critical reagent for elucidating the impact of amino acid substitutions on peptide-receptor interactions. By introducing a D-amino acid at position two, researchers can systematically assess how stereochemical inversion affects binding affinity, selectivity, and downstream signaling through GnRH receptors. Such comparative studies provide insight into the molecular determinants of agonist and antagonist activity, supporting rational peptide design and optimization efforts in endocrine research.
Receptor binding assays: The modified peptide is frequently employed in ligand-receptor binding experiments to quantify its affinity and specificity relative to native leuprolide and other analogs. Utilizing radioligand displacement or fluorescence-based assays, investigators can characterize the binding kinetics and receptor subtype selectivity conferred by the D-histidine substitution. These assays are instrumental in mapping receptor-ligand recognition domains and in developing next-generation peptide therapeutics or diagnostic probes.
Peptide stability and metabolic profiling: Incorporation of D-amino acids is a well-established strategy to enhance peptide resistance to proteolytic degradation. (D-His2)-Leuprolide Trifluoroacetic Acid Salt is routinely used in metabolic stability studies to evaluate its half-life and degradation pathways in biological matrices such as plasma or tissue homogenates. Such experiments inform on the pharmacokinetic properties of modified peptides and guide the development of analogs with improved in vivo persistence for research applications.
Peptide synthesis and analytical method development: The compound's defined sequence and salt form make it an ideal standard for validating solid-phase peptide synthesis protocols and analytical techniques, including high-performance liquid chromatography (HPLC) and mass spectrometry. It can be used to optimize purification conditions, calibrate detection methods, and assess the efficiency of peptide assembly and cleavage strategies, ensuring reproducibility and quality control in peptide production laboratories.
Functional studies of GnRH signaling: Researchers utilize (D-His2)-Leuprolide Trifluoroacetic Acid Salt to probe the physiological and biochemical consequences of GnRH receptor modulation in in vitro systems. By comparing its ability to activate or inhibit signal transduction pathways relative to unmodified leuprolide, investigators can dissect the role of specific residues in receptor activation, downstream effector recruitment, and cellular response mechanisms. These studies contribute to a deeper understanding of neuroendocrine regulation and the design of novel peptide-based research tools.
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