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 sophisticated carbohydrate-peptide conjugate that combines the unique properties of glycosylation with the well-established bioactivity of octreotide analogs. This compound features a glycoglycoyl group attached via a threonine linker to the octreotide peptide backbone, resulting in a molecule with enhanced solubility and stability compared to its non-glycosylated counterparts. Its structural design facilitates improved interaction with biological membranes and receptors, making it a valuable tool in biochemical and pharmacological research. The presence of the carbohydrate moiety not only influences the pharmacokinetic profile of the peptide but also allows for targeted studies on glycopeptide recognition and function. Researchers appreciate Glycoglycoyl-Thr-Octreotide for its versatility in experimental applications that require precise modulation of peptide activity and cellular uptake.
Receptor Binding Studies: Glycoglycoyl-Thr-Octreotide serves as an important probe in receptor binding assays, particularly for investigations involving somatostatin receptors. The carbohydrate modification can influence receptor affinity and selectivity, enabling researchers to dissect the role of glycosylation in peptide-receptor interactions. By comparing the binding characteristics of glycosylated versus non-glycosylated analogs, scientists can better understand the structural requirements for optimal receptor engagement and signal transduction.
Cellular Uptake Mechanisms: In the field of cellular biology, this glycopeptide is utilized to explore the mechanisms underlying peptide internalization and trafficking. The addition of the glycoglycoyl group may alter the uptake pathways, such as endocytosis or transporter-mediated entry, providing insights into how glycosylation affects cellular permeability. These studies are crucial for the development of peptide-based delivery systems and for enhancing the intracellular delivery of therapeutic agents.
Enzymatic Stability Assessment: Researchers employ Glycoglycoyl-Thr-Octreotide to evaluate the impact of glycosylation on peptide stability in the presence of proteolytic enzymes. The carbohydrate moiety can confer resistance to enzymatic degradation, extending the peptide's half-life in biological environments. Such stability assessments inform the design of more robust peptide analogs for research and biotechnological applications where prolonged activity is desirable.
Glycopeptide Recognition Studies: The unique structure of this compound makes it an excellent model for studying glycopeptide recognition by lectins, antibodies, or other carbohydrate-binding proteins. Investigations using this glycopeptide help elucidate the molecular basis of glycan-mediated interactions, which are fundamental to processes such as cell adhesion, signaling, and immune recognition. These insights can drive the development of novel glycopeptide-based probes and diagnostic tools.
Peptide Modification Research: Glycoglycoyl-Thr-Octreotide is also employed in studies focused on the effects of site-specific glycosylation on peptide conformation and function. By systematically modifying the peptide backbone with different carbohydrate groups, researchers can analyze changes in secondary structure, receptor affinity, and biological activity. This line of research supports the rational design of next-generation glycopeptide analogs with tailored properties for diverse scientific applications.
Bioconjugation and Targeted Delivery: Scientists leverage the unique chemical properties of this glycopeptide to develop advanced bioconjugation strategies and targeted delivery systems. The presence of both peptide and carbohydrate functional groups enables selective attachment to various biomolecules, nanoparticles, or surfaces, facilitating the construction of multifunctional research tools. These conjugates can be tailored for specific targeting, imaging, or therapeutic purposes in experimental settings, highlighting the compound's utility in cutting-edge biotechnological research.
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