Brevianamide F is a bicyclic diketopiperazine-derived natural product with rigid intramolecular constraints. The compact fused-ring system supports exploration of noncanonical folding motifs, aromatic interactions, and biosynthetic pathways. Researchers use it in conformational analysis and structure-activity exploration. Its architecture serves as a template for peptidomimetic design.
CAT No: R2214
CAS No:38136-70-8
Synonyms/Alias:Brevianamide F;38136-70-8;Cyclo-L-Trp-L-Pro;L-prolyl-L-tryptophan anhydride;cyclo-(Trp-Pro);(3s,8as)-3-(1h-Indol-3-Ylmethyl)hexahydropyrrolo[1,2-A]pyrazine-1,4-Dione;cyclo-L-Prolyl-L-tryptophanyl;cyclo-L-tryptophanyl-L-proline;CHEBI:64530;tryptophan-proline diketopiperazine;Cyclo(L-Trp-L-Pro);(3S,8aS)-3-((1H-Indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;L-tryptophyl-L-proline cyclic anhydride;cyclo-L-proline-L-pryptophan;cyclo-L-pryptophan-L-proline;76XZ426FPP;(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione;BrevianamideF;Brevianamide F?;(3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione;(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo(1,2-a)pyrazine-1,4-dione;(3S,8aS)-Hexahydro-3-(1H-indol-3-ylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione; Cyclo(L-Pro-L-Trp); Cyclo-L-tryptophyl-L-proline; L-Prolyl-L-tryptophan Anhydride Prolyltryptophanyldiketopiperazine; Cyclo-L-Prolyl-L-tryptophanyl;QRP;MFCD29917326;Cyclo(L-Pro-L-Trp);UNII-76XZ426FPP;Cyclo-L-tryptophyl-L-proline;CHEMBL563557;SCHEMBL2018181;DTXSID10959075;NBA13670;Brevianamide F; cyclo-L-Trp-L-Pro;s6751;AKOS027461197;CS-5688;AC-35169;AS-60483;DB-214849;HY-100385;C20563;Q25323862;(3S,8aS)-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione;(3S,8AS)-HEXAHYDRO-3-(1H-INDOL-3-YLMETHYL)PYRROLO(1,2-A)PYRAZINE-1,4-DIONE;
Brevianamide F is a naturally occurring diketopiperazine alkaloid isolated from various fungal species, particularly within the Penicillium and Aspergillus genera. Characterized by its unique bicyclo[2.2.2]diazaoctane core and indole-derived structure, Brevianamide F stands out for its complex architecture and chemical stability. Its intriguing framework has attracted attention from researchers interested in natural product synthesis, chemical biology, and the study of fungal metabolites. As a member of the brevianamide family, it provides a valuable scaffold for structural modification and mechanistic investigation, making it a significant compound in the field of organic and medicinal chemistry.
Natural Product Biosynthesis Research: Brevianamide F serves as a model compound for studying the biosynthetic pathways of indole alkaloids in fungi. Researchers utilize the compound to elucidate the enzymatic steps and genetic factors involved in its formation, providing insights into the metabolic capabilities of filamentous fungi. Through isotope labeling and gene knockout experiments, scientists can trace the origins and transformations of precursor molecules, shedding light on the broader family of diketopiperazine alkaloids. These studies not only advance fundamental understanding of fungal secondary metabolism but also inform strategies for the engineered biosynthesis of novel analogs with desired properties.
Synthetic Organic Chemistry: The unique bicyclic structure of Brevianamide F makes it an attractive target for synthetic chemists seeking to develop new methodologies and explore reaction mechanisms. Efforts to construct its complex core have driven innovation in cyclization, oxidation, and indole functionalization reactions. By serving as a benchmark for total synthesis, it challenges chemists to achieve high stereoselectivity and efficiency, often leading to the discovery of novel catalysts and synthetic routes. These advances have broader implications for the synthesis of related natural products and the design of structurally diverse libraries for biological screening.
Chemical Biology and Probe Development: Researchers employ Brevianamide F as a chemical probe to investigate biological processes in fungi and other organisms. Its structural features allow for the attachment of reporter groups or affinity tags, facilitating studies on protein-ligand interactions, cellular localization, and metabolite trafficking. By modifying the core structure, scientists can generate derivatives that selectively interact with specific biomolecules, illuminating pathways involved in fungal development, stress responses, or secondary metabolism. These chemical biology tools contribute to our understanding of small molecule function in complex biological systems.
Pharmacological Screening and Lead Discovery: Although not used clinically, Brevianamide F and its analogs are frequently evaluated in pharmacological assays to identify potential bioactivities. Its distinctive structure provides a starting point for screening against a variety of molecular targets, including enzymes, receptors, and signaling proteins. By testing libraries of brevianamide derivatives, researchers can uncover novel modulators of biological pathways, informing the early stages of drug discovery and the development of new molecular probes. The compound's natural origin and chemical diversity make it a valuable asset in exploratory pharmacology.
Fungal Ecology and Chemical Communication: In ecological studies, Brevianamide F is investigated for its role in fungal interactions and chemical signaling within microbial communities. Scientists explore how fungi deploy such secondary metabolites to compete for resources, deter predators, or establish symbiotic relationships. Through co-culture experiments and environmental sampling, it is possible to assess the ecological functions of brevianamides in soil, plant, or marine environments. Understanding these natural roles informs broader research into the chemical ecology of fungi and the potential applications of their metabolites in agriculture, biotechnology, and environmental management.
Brevianamide F continues to inspire research across multiple scientific disciplines due to its intricate structure, biosynthetic origins, and versatile reactivity. Its applications range from foundational studies in natural product biosynthesis and synthetic methodology development to advanced chemical biology, pharmacological exploration, and ecological investigation. As a representative compound of fungal secondary metabolism, it not only enriches our understanding of chemical diversity in nature but also provides a platform for innovation in chemical synthesis and molecular discovery.
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