Amanin contains a cyclic peptide architecture featuring tightly constrained backbone geometry. Its noncanonical residues contribute to structural rigidity and resistance to unfolding. Researchers explore its molecular-recognition properties and conformational stability. Applications include toxin-analogue modeling, structural biology, and constrained-peptide research.
CAT No: R2683
CAS No:21150-21-0
Synonyms/Alias:AMANIN;Amanine;UNII-VIW95I76GY;VIW95I76GY;21150-21-0;HSDB 3457;DTXSID70895849;BRN 1070214;alpha-Amanitin, 1-L-aspartic acid-4-(2-mercapto-L-tryptophan)-;9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8, 9)(1,5,8,11,14)thiatetraaza cyclooctadecino(18,17-b)indole-6-acetic acid, 1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-21-(2,3-dihydroxy-1-methylpropyl)-2-hydroxy-5,8,20,23,24,27,30,33-octaoxo-, 11-oxide;9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8,9)(1,5,8,11,14)thiatetraazacyclooctadecino(18,17-b)indole-6-acetic acid, 1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-21-(2,3-dihydroxy-1-methylpropyl)-2-hydroxy-5,8,20,23,24,27,30,33-octaoxo-, 11-oxide;2-((1S,4S,8R,10S,13S,16S,34S)-34-((2S)-butan-2-yl)-13-((2R,3R)-3,4-dihydroxybutan-2-yl)-8-hydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo(14.12.11.06,10.018,26.019,24)nonatriaconta-18(26),19,21,23-tetraen-4-yl)acetic acid;2-(34-(butan-2-yl)-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo(14.12.11.06,10.018,26.019,24)nonatriaconta-18(26),19,21,23-tetraen-4-yl)acetic acid;2-[(1S,4S,8R,10S,13S,16S,34S)-34-[(2S)-butan-2-yl]-13-[(2R,3R)-3,4-dihydroxybutan-2-yl]-8-hydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid;2-[34-(butan-2-yl)-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid;.ALPHA.-AMANITIN, 1-L-ASPARTIC ACID-4-(2-MERCAPTO-L-TRYPTOPHAN)-;DTXCID801325348;CYCLO(L-.ALPHA.-ASPARTYL-4-HYDROXY-L-PROLYL-(R)-4,5-DIHYDROXY-L-ISOLEUCYL-2-MERCAPTO-L-TRYPTOPHYLGLYCYL-L-ISOLEUCYLGLYCYL-L-CYSTEINYL) CYCLIC (4->8)-SULFIDE (R)-S-OXIDE;alphaAmanitin, 1Laspartic acid4(2mercaptoLtryptophan);1-L-aspartic acid-4-(2-mercapto-L-tryptophan)-alpha-amanitin;9,18 (Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8, 9)(1,5,8,11,14)thiatetraaza cyclooctadecino(18,17b)indole 6acetic acid, 1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23aoctadecahydro29secbutyl21(2,3dihydroxy1methylpropyl)2hydroxy5,8,20,23,24,27,30,33octaoxo, 11oxide;CYCLO(L-ALPHA-ASPARTYL-4-HYDROXY-L-PROLYL-(R)-4,5-DIHYDROXY-L-ISOLEUCYL-2-MERCAPTO-L-TRYPTOPHYLGLYCYL-L-ISOLEUCYLGLYCYL-L-CYSTEINYL) CYCLIC (4->8)-SULFIDE (R)-S-OXIDE;
Amanin is a naturally occurring cyclic peptide toxin classified within the amatoxin family, renowned for its potent inhibitory effects on RNA polymerase II. Isolated primarily from certain species of the Amanita genus of mushrooms, this bicyclic octapeptide is characterized by a unique structural motif that confers remarkable stability and biological activity. Its high affinity for eukaryotic RNA polymerase II and the consequential disruption of transcriptional processes have made it a compound of significant interest in molecular biology, toxicology, and biochemical research. The specificity and mechanism of action of amanin provide a valuable model for studying protein-nucleic acid interactions and cellular responses to transcriptional inhibition.
Mechanistic toxicology studies: As a prototypical amatoxin, amanin is extensively employed in mechanistic investigations of cellular toxicity, particularly in the context of transcriptional arrest. By binding to and inhibiting RNA polymerase II, it serves as a precise tool for dissecting the molecular events that follow transcriptional blockade, including the downstream effects on mRNA synthesis, protein expression, and programmed cell death. Researchers utilize this peptide to model acute toxic responses, facilitating the elucidation of cellular defense mechanisms and pathways involved in toxin-induced apoptosis.
Transcriptional regulation research: The selective inhibition of RNA polymerase II by amanin allows for controlled studies of gene expression regulation in eukaryotic systems. It provides a means to temporally and spatially modulate transcriptional activity, enabling researchers to investigate the dynamics of mRNA turnover, the stability of nascent transcripts, and the interplay between transcription and other nuclear processes. Such studies are instrumental in advancing the understanding of gene regulatory networks and the cellular consequences of disrupted transcription.
Cellular response and stress pathway analysis: The use of amatin in cell-based assays enables the exploration of stress response pathways activated upon transcriptional inhibition. By inducing a defined and potent block in RNA synthesis, researchers can monitor the activation of signaling cascades such as the unfolded protein response, autophagy, and DNA damage repair mechanisms. These insights are crucial for mapping the cellular adaptation to transcriptional stress and for identifying potential molecular targets involved in cytoprotection or susceptibility.
Peptide structure-activity relationship (SAR) studies: Owing to its well-defined cyclic peptide structure, amanin serves as a model system for structure-activity relationship investigations within the amatoxin family. Synthetic modifications and analog development based on its scaffold allow for detailed analysis of the relationship between specific amino acid residues, conformational features, and biological activity. Such SAR studies contribute to a deeper understanding of peptide-protein interactions and inform the rational design of novel peptide-based inhibitors or probes.
Analytical method development and reference standard: The unique chemical and biological properties of amanin make it a valuable reference compound in the development and validation of analytical methods for amatoxin detection. Its use as a standard in chromatographic and mass spectrometric assays supports the accurate identification and quantification of related toxins in complex biological or environmental samples. This application is particularly relevant for research on mushroom poisoning, environmental monitoring, and forensic investigations, where precise detection is essential for risk assessment and scientific study.
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