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 indole alkaloid belonging to the diketopiperazine family, originally isolated from Penicillium species. This secondary metabolite is characterized by its unique bicyclo[2.2.2]diazaoctane core and complex stereochemistry, which have attracted significant attention in the fields of natural product chemistry and biosynthetic pathway elucidation. As a structurally intriguing fungal metabolite, Brevianamide F serves as a valuable model for studying enzymatic cyclization and oxidative transformations, offering insights into the chemical diversity and biosynthetic logic of fungal secondary metabolites. Its role as a biosynthetic precursor to more complex brevianamides and related alkaloids further underscores its importance in chemical biology and synthetic organic chemistry research.
Natural product biosynthesis studies: Researchers frequently employ Brevianamide F as a key probe in elucidating the biosynthetic pathways of indole alkaloids within filamentous fungi. By tracing its formation and subsequent conversion to structurally related metabolites, investigators can dissect the sequence of enzymatic steps and identify novel biosynthetic enzymes involved in diketopiperazine assembly and functionalization. The compound's well-defined structure and positioning as an intermediate make it highly informative for feeding experiments, isotope labeling studies, and gene knockout approaches aimed at mapping the molecular logic of secondary metabolite production.
Synthetic methodology development: The unique molecular architecture of Brevianamide F provides an exceptional platform for the development and validation of synthetic strategies targeting complex bicyclic alkaloids. Synthetic chemists use it as a benchmark substrate for exploring novel cyclization reactions, stereoselective functionalizations, and total synthesis approaches. Its challenging framework has inspired the creation of innovative methodologies that are applicable to a broader array of natural products, thereby advancing the field of synthetic organic chemistry and enabling access to structurally diverse analogs for further study.
Chemical ecology investigations: As a representative fungal secondary metabolite, Brevianamide F is studied for its ecological role in the natural environment of its producing organisms. Researchers examine its potential involvement in interspecies chemical signaling, defense mechanisms, or microbial competition. By analyzing its production and distribution in various fungal strains, scientists gain insight into the adaptive significance and evolutionary pressures shaping the secondary metabolite repertoire of filamentous fungi.
Analytical reference standard: The compound is utilized as an authentic analytical standard in the qualitative and quantitative assessment of fungal extracts. Its well-characterized spectroscopic properties, including NMR and mass spectrometry signatures, facilitate the accurate identification and quantification of brevianamide-related compounds in complex biological samples. This application is crucial for dereplication workflows, metabolomic profiling, and the discovery of novel analogs in natural product screening programs.
Structure-activity relationship (SAR) studies: The availability of Brevianamide F enables systematic investigation of structural determinants underlying the biological properties of diketopiperazine alkaloids. By comparing its physicochemical and biological characteristics with those of structurally modified analogs, researchers can delineate key functional groups and stereochemical features essential for molecular recognition and activity in biological assays. These SAR studies inform the rational design of new compounds with tailored properties for use in chemical biology, probe development, or as leads for further research applications.
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