Glycoglycoyl-Thr-Octreotide incorporates a glycoacylated threonine into the octreotide backbone, enhancing hydrophilicity and local steric complexity. The modified side chain modulates hydrogen-bond networks and backbone organization. Researchers compare its folding and binding features with unmodified analogues. Uses include glycosylation-motif modeling, peptide stability work, and receptor-interaction analysis.
CAT No: Z10-101-216
Synonyms/Alias:2-((1R)-1-((4R,7S,10S,13R,16S,19R)-13-((1H-Indol-3-yl)methyl)-19-(2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-benzyl-4-((1,3-dihydroxybutan-2-yl)carbamoyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-7-yl)ethoxy)-2-oxoethyl 2-hydroxyacetate; D-Phenylalanyl - L-hemicystyl - L-phenylalanyl - D-tryptophyl - L-lysyl - L-threonyl - L-hemicystyl - (O-Glycoglycoyl) - L-Threoninol - cyclic (2à7) - disulfide; (2R,3R)-3-((4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-19-((R)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-benzyl-7-((R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamido)-4-hydroxybutan-2-yl 2-(2-hydroxyacetoxy)acetate
Glycoglycoyl-Thr-Octreotide is a synthetic peptide analog that integrates a glycosylated modification into the well-characterized octreotide scaffold, incorporating threonine and a glycoglycoyl moiety. As a specialized peptide construct, it merges the biological properties of somatostatin analogs with enhanced hydrophilicity and potential receptor-binding diversity imparted by glycosylation. Its unique structure makes it a valuable tool in peptide research, particularly for investigating the effects of glycosylation on peptide stability, receptor selectivity, and bioactivity. The compound's design enables researchers to explore advanced peptide engineering strategies and gain deeper insights into the modulation of peptide-based signaling pathways.
Peptide receptor interaction studies: Glycoglycoyl-Thr-Octreotide serves as an effective probe for dissecting somatostatin receptor subtype specificity and binding kinetics. The presence of a glycosylated side chain allows for comparative studies against non-glycosylated analogs, enabling researchers to evaluate how glycan modifications influence receptor affinity, selectivity, and downstream signaling. Such investigations are instrumental in mapping the structural determinants of peptide-receptor interactions and in guiding the rational design of next-generation peptide ligands.
Peptide stability and pharmacokinetics research: Incorporation of glycosyl groups into peptide frameworks is a recognized strategy for enhancing proteolytic stability and modulating in vivo pharmacokinetics. This glycosylated octreotide analog provides a platform for evaluating the impact of carbohydrate moieties on peptide degradation rates, serum half-life, and resistance to enzymatic cleavage. By comparing its stability profile to that of unmodified octreotide, researchers can elucidate structure-stability relationships that inform the design of more robust peptide therapeutics and molecular probes.
Glycopeptide synthesis and analytical method development: As a structurally defined glycopeptide, Glycoglycoyl-Thr-Octreotide is highly relevant for optimizing synthetic methodologies and analytical techniques in peptide chemistry. Its use supports the validation of solid-phase peptide synthesis protocols involving glycosylation steps, as well as the refinement of chromatographic and mass spectrometric methods for glycopeptide characterization. These applications are critical for advancing the field of peptide synthesis, ensuring reproducibility, and expanding the toolkit available for complex peptide modification.
Cell signaling and functional assays: The compound's ability to mimic endogenous somatostatin analogs while introducing novel glycosylation patterns makes it an excellent candidate for in vitro functional assays. It can be employed to investigate the modulation of cyclic AMP levels, calcium signaling, or other second messenger systems in cultured cells expressing somatostatin receptors. Such studies contribute to a better understanding of how glycan modifications can fine-tune receptor-mediated cellular responses, providing valuable data for both basic research and applied peptide science.
Peptide-based biomaterials and conjugate development: The distinctive chemical features of Glycoglycoyl-Thr-Octreotide, including its glycosylated threonine residue, offer opportunities for its incorporation into peptide-based biomaterials or as a building block for conjugate synthesis. Researchers can utilize it to explore the effects of glycopeptide incorporation on the biophysical properties, biofunctionality, and surface characteristics of engineered materials. This line of investigation is particularly relevant for the design of advanced biomaterials with tailored cell-interactive or bioresponsive features, broadening the scope of peptide applications beyond traditional biochemical research.
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