Trp(4-hydroxybenzyl)25-Semaglutide contains a modified tryptophan residue offering additional π-stacking and hydrogen-bonding potential. Researchers investigate how the 4-hydroxybenzyl moiety alters folding, receptor binding, and hydrophobic packing. The analog provides insights into semaglutide's structure-activity determinants. Applications include peptide engineering, analog comparison, and conformational analysis.
CAT No: R2863
Synonyms/Alias:H-His-Aib-Glu-Gly-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gln-Gln-Ala-Ala-Lys-(Oct-gamma-AEEAc-AEEAA)Glu-Phe-lle-Ala-Trp(p-OH-Benzyl)-Leu-Val-Arg-Gly-Arg-Gly-OH; (3S,12S,15S,18S,21S,24S,27S,30S,33S,36S,39S,45S,48S,51S,54S,81S)-3-(2-((R)-2-Amino-3-(1H-imidazol-4-yl)propanamido)-2-methylpropanamido)-45-(3-amino-3-oxopropyl)-54-(((6S,12S,15S,18S,21S,24S,27S,30S,33S)-1-amino-30-benzyl-27-((S)-sec-butyl)-35-carboxy-6-((carboxymethyl)carbamoyl)-12-(3-guanidinopropyl)-21-((2-(4-hydroxybenzyl)-1H-indol-3-yl)methyl)-1-imino-18-isobutyl-15-isopropyl-24-methyl-8,11,14,17,20,23,26,29,32-nonaoxo-2,7,10,13,16,19,22,25,28,31-decaazapentatriacontan-33-yl)carbamoyl)-12-benzyl-39-(2-carboxyethyl)-21-(carboxymethyl)-33-(4-hydroxybenzyl)-9,15-bis((R)-1-hydroxyethyl)-18,27,30-tris(hydroxymethyl)-36-isobutyl-24-isopropyl-48,51-dimethyl-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,60,69,78,83-henicosaoxo-62,65,71,74-tetraoxa-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,59,68,77,82-henicosaazanonanonacontane-1,81,99-tricarboxylic Acid;
Trp(4-hydroxybenzyl)25-Semaglutide is a synthetic peptide analog engineered through the site-specific incorporation of a modified tryptophan residue at position 25 within the semaglutide backbone. As a structurally tailored glucagon-like peptide-1 (GLP-1) receptor agonist analog, it combines the pharmacological relevance of semaglutide with the unique biochemical properties conferred by the 4-hydroxybenzyl modification. This compound is of significant interest in peptide chemistry, receptor pharmacology, and molecular engineering, serving as a valuable research tool for the elucidation of structure-activity relationships and peptide-receptor interactions. Its distinct modification allows for the exploration of hydrogen bonding, aromatic stacking, and electronic effects within the peptide's functional context, supporting advanced studies in peptide design and function.
Peptide structure-activity relationship (SAR) studies: The incorporation of 4-hydroxybenzyl-tryptophan at position 25 enables researchers to systematically investigate how specific side-chain modifications influence the biological activity, receptor binding affinity, and conformational stability of GLP-1 analogs. By comparing the functional behavior of this analog to native semaglutide and other variants, scientists can delineate the role of aromatic substitution in modulating peptide-receptor recognition and downstream signaling, advancing rational peptide optimization strategies.
Receptor binding and signaling assays: The modified peptide serves as a powerful probe in in vitro assays designed to assess GLP-1 receptor engagement, activation kinetics, and downstream signal transduction. Its unique side-chain chemistry may alter receptor contacts or allosteric modulation, providing insight into the molecular determinants of agonist efficacy and selectivity. Such studies facilitate the mapping of key interaction sites and help refine models of peptide-GPCR interactions.
Peptide stability and metabolic profiling: The presence of a noncanonical amino acid at a critical position within the peptide sequence allows for detailed examination of proteolytic stability and metabolic fate. Researchers can utilize this analog to assess resistance to enzymatic degradation, evaluate half-life extension strategies, and monitor metabolic transformations using advanced analytical techniques such as mass spectrometry and HPLC. These investigations inform the design of more robust peptide therapeutics and research tools.
Analytical method development: The distinct chemical signature of the 4-hydroxybenzyl group provides an analytical handle for the development and validation of sensitive detection methods. Laboratories can employ this analog as a reference standard or internal control in chromatographic, spectrometric, or immunoassay platforms. Its defined structural modification aids in optimizing assay specificity, quantification accuracy, and method robustness in peptide analysis workflows.
Peptide synthesis and engineering research: As a model system for incorporating nonstandard amino acids into complex peptides, this analog supports methodological advances in solid-phase peptide synthesis, orthogonal protection strategies, and post-synthetic modification techniques. Its use enables peptide chemists to refine coupling protocols, optimize reaction conditions, and evaluate the compatibility of novel side-chain functionalities, thereby expanding the toolkit for peptide engineering and chemical biology applications.
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