Emerimicin Ⅳ
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| Category | Antibiotics |
| Catalog number | BBF-01213 |
| CAS | 52931-43-8 |
| Molecular Weight | 1573.87 |
| Molecular Formula | C77H120N16O19 |
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Description
It is produced by the strain of Emericellopsis microspora. It mainly has activity against gram-positive bacteria. Emerimicin II activity is stronger than the Emerimicin III and IV.
Specification
| Synonyms | samarosporin I; Stilbellin I |
| IUPAC Name | (2R)-2-[[(2S,4R)-1-[2-[[2-[[(2R)-2-[[2-[[(2R)-2-[[2-[[2-[[2-[[(2R)-2-acetamido-3-phenylpropanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-N-[(2R)-1-[(2S,4S)-4-hydroxy-2-[[1-[[(2R)-1-hydroxy-3-phenylpropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-methyl-1-oxobutan-2-yl]pentanediamide |
| Canonical SMILES | CCC(C)(C(=O)N1CC(CC1C(=O)NC(C)(C)C(=O)NC(CC2=CC=CC=C2)CO)O)NC(=O)C(CCC(=O)N)NC(=O)C3CC(CN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(CC4=CC=CC=C4)NC(=O)C)O |
| InChI | InChI=1S/C77H120N16O19/c1-20-77(19,70(112)93-40-49(97)37-54(93)62(104)87-71(7,8)64(106)81-47(41-94)34-45-27-23-21-24-28-45)88-58(100)50(31-32-55(78)98)83-61(103)53-36-48(96)39-92(53)69(111)76(17,18)91-67(109)74(13,14)85-59(101)51(33-42(2)3)82-56(99)38-79-63(105)57(43(4)5)84-65(107)72(9,10)89-68(110)75(15,16)90-66(108)73(11,12)86-60(102)52(80-44(6)95)35-46-29-25-22-26-30-46/h21-30,42-43,47-54,57,94,96-97H,20,31-41H2,1-19H3,(H2,78,98)(H,79,105)(H,80,95)(H,81,106)(H,82,99)(H,83,103)(H,84,107)(H,85,101)(H,86,102)(H,87,104)(H,88,100)(H,89,110)(H,90,108)(H,91,109)/t47-,48-,49+,50-,51-,52-,53+,54+,57-,77-/m1/s1 |
| InChI Key | LSJHBSMFQYTUER-AWPSBPSCSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 243-245 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Tolypocladamides A-G: Cytotoxic Peptaibols from Tolypocladium inflatum
Sarath P D Senadeera, Dongdong Wang, Chang-Kwon Kim, Emily A Smith, David E Durrant, Patrick A Alexander, Karen L Wendt, Andrew G Stephen, Deborah K Morrison, Robert H Cichewicz, Curtis J Henrich, John A Beutler J Nat Prod. 2022 Jun 24;85(6):1603-1616. doi: 10.1021/acs.jnatprod.2c00240. Epub 2022 Jun 13.
Seven new peptaibols named tolypocladamides A-G have been isolated from an extract of the fungus Tolypocladium inflatum, which inhibits the interaction between Raf and oncogenic Ras in a cell-based high-throughput screening assay. Each peptaibol contains 11 amino acid residues, an octanoyl or decanoyl fatty acid chain at the N-terminus, and a leucinol moiety at the C-terminus. The peptaibol sequences were elucidated on the basis of 2D NMR and mass spectral fragmentation analyses. Amino acid configurations were determined by advanced Marfey's analyses. Tolypocladamides A-G caused significant inhibition of Ras/Raf interactions with IC50 values ranging from 0.5 to 5.0 μM in a nanobioluminescence resonance energy transfer (NanoBRET) assay; however, no interactions were observed in a surface plasmon resonance assay for binding of the compounds to wild type or G12D mutant Ras constructs or to the Ras binding domain of Raf. NCI 60 cell line testing was also conducted, and little panel selectivity was observed.
2. Emerimicins V-X, 15-Residue Peptaibols Discovered from an Acremonium sp. through Integrated Genomic and Chemical Approaches
Guangwei Wu, Bryn T M Dentinger, Jason R Nielson, Randall T Peterson, Jaclyn M Winter J Nat Prod. 2021 Apr 23;84(4):1113-1126. doi: 10.1021/acs.jnatprod.0c01186. Epub 2021 Feb 22.
Fermentation of Acremonium tubakii W. Gams isolated from a soil sample collected from the University of Utah led to the isolation and characterization of six new linear pentadecapeptides, emerimicins V-X (1-6). Peptaibols containing 15-residues are quite rare, with only 22 reported. Genome mining and bioinformatic analysis were used to identify the emerimicin 60 kbp eme biosynthetic cluster harboring a single 16-module hybrid polyketide-nonribosomal peptide synthetase. A detailed bioinformatic investigation of the corresponding 15 adenylation domains, combined with 1D and 2D NMR experiments, LC-MS/MS data, and advanced Marfey's method, allowed for the elucidation and absolute configuration of all proteinogenic and nonproteinogenic amino acid residues in 1-6. As some peptaibols possess cytotoxic activity, a zebrafish embryotoxicity assay was used to evaluate the toxicity of the six emerimicins and showed that emerimicin V (1) and VI (2) exhibit the most potent activity. Additionally, out of the six emerimicins, 1 displayed modest activity against Enterococcus faecalis, methicillin-resistant Staphylococcus aureus, and vancomycin-resistant Enterococcus faecium with MIC values of 64, 32, and 64 μg/mL, respectively.
3. Tolypocladamide H and the Proposed Tolypocladamide NRPS in Tolypocladium Species
Richard M Tehan, Rheannon R Blount, Ryan L Goold, Daphne R Mattos, Nicolas R Spatafora, Javier F Tabima, Romina Gazis, Chengshu Wang, Jane E Ishmael, Joseph W Spatafora, Kerry L McPhail J Nat Prod. 2022 May 27;85(5):1363-1373. doi: 10.1021/acs.jnatprod.2c00153. Epub 2022 May 2.
The genome of entomopathogenic fungus Tolypocladium inflatum Gams encodes 43 putative biosynthetic gene clusters for specialized metabolites, although genotype-phenotype linkages have been reported only for the cyclosporins and fumonisins. T. inflatum was cultured in defined minimal media, supplemented with or without one of nine different amino acids. Acquisition of LC-MS/MS data for molecular networking and manual analysis facilitated annotation of putative known and unknown metabolites. These data led us to target a family of peptaibols and guided the isolation and purification of tolypocladamide H (1), which showed modest antibacterial activity and toxicity to mammalian cells at micromolar concentrations. HRMS/MS, NMR, and advanced Marfey's analysis were used to assign the structure of 1 as a peptaibol containing 4-[(E)-2-butenyl]-4-methyl-l-threonine (Bmt), a hallmark structural motif of the cyclosporins. LC-MS detection of homologous tolypocladamide metabolites and phylogenomic analyses of peptaibol biosynthetic genes in other cultured Tolypocladium species allowed assignment of a putative tolypocladamide nonribosomal peptide synthetase gene.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
