Segetalin B is a plant-derived cyclic peptide featuring unusual amino acids and constrained backbone geometry. The macrocycle confers significant resistance to proteolytic degradation and defines a rigid pharmacophore. Researchers examine its interaction with membranes and proteins using spectroscopic and computational tools. Applications include natural-product analog development, conformational analysis, and bioactive scaffold design.
CAT No: R2577
CAS No:164991-89-3
Synonyms/Alias:SEGETALIN B;164991-89-3;(3S,6S,9S,12S)-6-(1H-indol-3-ylmethyl)-3,9-dimethyl-12-propan-2-yl-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone;Segetalin-B;SCHEMBL151686;CHEMBL386632;AKOS040760076;DA-77779;MS-29005;HY-107245;CS-0027753;E88615;(3S,6S,9S,12S)-6-(1H-indol-3-ylmethyl)-12-isopropyl-3,9-dimethyl-1,4,7,10,13-pentaazacyclopentadecane-2,5,8,11,14-pentone;
Segetalin B is a naturally occurring cyclic peptide originally isolated from the seeds of Vaccaria segetalis. As a member of the cyclopeptide family, it is characterized by a stable, constrained ring structure that imparts unique biochemical properties, including enhanced resistance to proteolytic degradation and the potential for diverse molecular interactions. Its distinctive amino acid sequence and conformational rigidity have made it a subject of interest in peptide chemistry, molecular recognition studies, and natural product research. The compound's structural features and bioactive potential place it at the intersection of chemical biology, peptide engineering, and plant-derived secondary metabolite investigations.
Peptide structure-activity relationship studies: Segetalin B serves as a valuable model for elucidating the relationship between peptide conformation and biological activity. Its cyclic backbone allows researchers to investigate how ring size, sequence motifs, and side-chain orientations influence receptor binding, molecular recognition, or enzymatic stability. By comparing the activity profiles of Segetalin B with its linear or structurally modified analogues, scientists can gain insight into the principles governing peptide-target interactions, which is essential for the rational design of novel bioactive peptides or peptide-based inhibitors.
Peptide synthesis and cyclization methodology development: The unique cyclization pattern and amino acid composition of Segetalin B make it an excellent reference compound for developing and optimizing synthetic strategies in peptide chemistry. Researchers employ it as a benchmark for evaluating new cyclization protocols, solid-phase synthesis techniques, or protecting group strategies. Its use in these contexts helps advance methodologies for constructing complex cyclic peptides, which are increasingly important in drug discovery, biomaterials, and chemical biology.
Natural product biosynthesis research: As a representative cyclopeptide from plant sources, Segetalin B provides a foundation for studying the biosynthetic pathways responsible for cyclic peptide formation in higher plants. Investigations utilizing this compound can help decipher enzyme mechanisms, precursor peptide processing, and post-translational modifications involved in cyclopeptide biosynthesis. Such studies contribute to a broader understanding of plant secondary metabolism and may inform biotechnological approaches for producing novel cyclic peptides with tailored properties.
Analytical method development and standardization: The well-defined structure of Segetalin B makes it a useful analytical standard for developing and validating chromatographic, mass spectrometric, or spectroscopic techniques. Its application in these areas enables accurate identification, quantification, and purity assessment of cyclic peptides in complex biological matrices or synthetic mixtures. Employing Segetalin B as a reference compound supports the advancement of high-precision analytical workflows in both academic and industrial laboratories.
Molecular probe and ligand discovery: Due to its stable cyclic framework and propensity for specific molecular interactions, Segetalin B is utilized as a scaffold for the development of molecular probes or as a lead structure in ligand discovery efforts. Researchers modify its sequence or functional groups to generate libraries of analogues for screening against biological targets, facilitating the identification of new binding motifs or functional domains. This approach underpins the exploration of structure-based ligand design and the expansion of chemical space accessible via cyclic peptides.
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