L-Lactolactoyl-Phe-Octreotide introduces a lactoyl moiety on phenylalanine within the octreotide framework, increasing polarity and hydrogen-bonding capacity. Researchers analyze shifts in conformational preferences and receptor-binding features. The modification influences solubility and matrix interactions. Applications include modified-analogue evaluation, biophysical analysis, and peptide-ligand engineering.
CAT No: Z10-101-214
Synonyms/Alias:(N-L-Lactolactoyl)-D-Phenylalanyl-L-hemicystyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-L-hemicystyl-L-Threoninol cyclic(27)-disulfide; (R)-1-(((R)-1-(((4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-10-(4-aminobutyl)-16-benzyl-4-(((2R,3R)-1,3-dihydroxybutan-2-yl)carbamoyl)-7-((R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxopropan-2-yl(R)-2-hydroxypropanoate
L-Lactolactoyl-Phe-Octreotide is a synthetic peptide conjugate that combines the well-characterized somatostatin analog octreotide with a modified phenylalanine residue bearing an L-lactolactoyl group. As a chemically engineered peptide, it harnesses the selective receptor-binding properties of octreotide while introducing a lactolactoyl modification, which can influence peptide stability, bioavailability, or targeted delivery in biochemical research. The unique structure of this conjugate makes it a valuable tool for probing peptide-receptor interactions, studying post-translational modifications, and developing advanced peptide-based research methodologies. Its design supports the investigation of structure-activity relationships and functional optimization within peptide science.
Peptide receptor binding studies: L-Lactolactoyl-Phe-Octreotide is highly relevant in the context of analyzing somatostatin receptor interactions. The octreotide core enables selective engagement with somatostatin receptor subtypes, while the lactolactoyl modification at the phenylalanine site offers an opportunity to assess how chemical alterations affect receptor affinity and signaling. Researchers can use this conjugate in competitive binding assays, receptor profiling, and structure-activity relationship studies to elucidate the impact of peptide modifications on receptor selectivity and downstream signaling pathways.
Peptide stability and metabolic profiling: The incorporation of the L-lactolactoyl group provides a strategic site for investigating peptide stability, enzymatic degradation, and metabolic fate in vitro. Studies utilizing this conjugate can reveal how lactolactoyl modifications influence proteolytic resistance, peptide half-life, and susceptibility to metabolic enzymes. Such research supports the rational design of peptides with enhanced stability for research applications, as well as the development of analytical protocols to monitor peptide metabolites and degradation products in complex biological matrices.
Peptide synthesis and modification research: As a model compound, L-Lactolactoyl-Phe-Octreotide is instrumental for evaluating synthetic strategies involving site-specific acylation or conjugation of bioactive peptides. Its structure enables peptide chemists to optimize solid-phase synthesis protocols, test the compatibility of lactolactoyl modifications with various protecting groups, and refine purification and characterization methods for modified peptides. These insights facilitate the broader application of post-synthetic modifications in peptide engineering and functionalization.
Analytical method development: The unique physicochemical properties imparted by the lactolactoyl-phenylalanine moiety make this peptide conjugate a valuable reference standard for the development and validation of analytical techniques. Researchers can employ it in mass spectrometry, high-performance liquid chromatography (HPLC), and capillary electrophoresis to optimize detection, quantification, and separation of structurally related peptides. Its defined structure aids in calibrating analytical instruments, validating assay sensitivity, and benchmarking method robustness for peptide analysis.
Functional studies in cellular models: The selective receptor-targeting capability of octreotide-based peptides, combined with the altered chemical characteristics of the lactolactoyl modification, enables advanced functional studies in cultured cells expressing somatostatin receptors. Investigators can utilize this compound to assess receptor-mediated signaling, internalization, and trafficking, as well as to explore the influence of peptide modifications on cellular uptake and intracellular processing. Such studies contribute to a deeper understanding of peptide-receptor dynamics and inform the design of next-generation peptide probes for cellular and molecular research.
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