Emerimicin IIA
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| Category | Antibiotics |
| Catalog number | BBF-03738 |
| CAS | 79395-86-1 |
| Molecular Weight | 1825.15 |
| Molecular Formula | C89H137N19O22 |
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Description
It is produced by the strain of Emericellopsis microspora. It mainly has activity against gram-positive bacteria and various protozoa. The activity of Emerimicin II is stronger than the Emerimicin III and IV.
Specification
| Synonyms | Ac-Trp-Ile-Gln-Aib-Ile-Thr-Aib-Leu-Aib-Hyp-Gln-Aib-Hyp-Aib-Unk; Zervamicin-II-A; Zervamicin IIA; Zervamicin IC, 3-L-glutamine-4-(2-methylalanine)-; L-Prolinamide, N-acetyl-L-tryptophyl-L-isoleucyl-L-glutaminyl-2-methylalanyl-L-isoleucyl-L-threonyl-2-methylalanyl-L-leucyl-2-methylalanyl-(4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prolyl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]- |
| IUPAC Name | (2S)-2-[[(2S,4R)-1-[2-[[(2S)-2-[[2-[[(2S,3R)-2-[[(2S,3S)-2-[[2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-acetamido-3-(1H-indol-3-yl)propanoyl]amino]-3-methylpentanoyl]amino]-5-amino-5-oxopentanoyl]amino]-2-methylpropanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-2-methylpropanoyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-N-[1-[(2S,4R)-2-[[1-[(1R,2S)-2-carbamoyl-1-(1-hydroxy-3-phenylpropan-2-yl)pyrrolidin-1-ium-1-yl]-2-methyl-1-oxopropan-2-yl]carbamoyl]-4-hydroxypyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]pentanediamide |
| Canonical SMILES | CCC(C)C(C(=O)NC(CCC(=O)N)C(=O)NC(C)(C)C(=O)NC(C(C)CC)C(=O)NC(C(C)O)C(=O)NC(C)(C)C(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)N1CC(CC1C(=O)NC(CCC(=O)N)C(=O)NC(C)(C)C(=O)N2CC(CC2C(=O)NC(C)(C)C(=O)[N+]3(CCCC3C(=O)N)C(CC4=CC=CC=C4)CO)O)O)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C |
| InChI | InChI=1S/C89H137N19O22/c1-19-47(5)67(98-71(117)61(94-50(8)111)39-52-42-93-57-30-25-24-29-56(52)57)77(123)96-59(33-35-66(91)115)72(118)101-86(11,12)81(127)100-68(48(6)20-2)78(124)99-69(49(7)110)79(125)105-85(9,10)80(126)97-60(37-46(3)4)74(120)103-88(15,16)82(128)106-43-54(112)40-62(106)75(121)95-58(32-34-65(90)114)73(119)102-87(13,14)83(129)107-44-55(113)41-63(107)76(122)104-89(17,18)84(130)108(36-26-31-64(108)70(92)116)53(45-109)38-51-27-22-21-23-28-51/h21-25,27-30,42,46-49,53-55,58-64,67-69,93,109-110,112-113H,19-20,26,31-41,43-45H2,1-18H3,(H17-,90,91,92,94,95,96,97,98,99,100,101,102,103,104,105,111,114,115,116,117,118,119,120,121,122,123,124,125,126,127)/p+1/t47-,48-,49+,53?,54+,55+,58-,59-,60-,61-,62-,63-,64-,67-,68-,69-,108+/m0/s1 |
| InChI Key | DRBLMTOLAHVBGB-CKVKIVNWSA-O |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 261°C (dec.) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Self-aggregation properties of spin-labeled zervamicin IIA as studied by PELDOR spectroscopy
A D Milov, Yu D Tsvetkov, E Yu Gorbunova, L G Mustaeva, T V Ovchinnikova, J Raap Biopolymers. 2002 Sep;64(6):328-36. doi: 10.1002/bip.10208.
In this article, the pulsed double electron-electron resonance in electron spin-echo (PELDOR) technique is applied to study the self-aggregation of spin-labeled zervamicin IIA, a hexadecapeptide antibiotic of fungal origin, which is known to form ion channels in a phospholipid double layer. Measurements of the ion channel forming properties and the antibiotic activity of the analog indicate that replacement of the C-terminal phenylalaninol by the amino-2,2,6,6-tetramethylpiperidinyloxy (TEMPO) residue does not influence the biophysical and biological properties. The dipole-dipole interaction between the spin labels of the fully biologically active peptide analog was studied in frozen (77 K) glassy solutions in different ratios of toluene-methanol. The spin-labeled zervamicin IIA molecules were shown to form aggregates. An average distance between the spin labels in the aggregates was estimated to be in the range of 25-35 A (depending on the solvent composition), indicating that the amphiphilic helical peptide molecules are oriented in an antiparallel fashion. Increasing of methanol content in the solution results in a loosening of the aggregate structure. It was shown that the fraction of aggregated zervamicin IIA molecules is less than 44-67% depending on the solvent composition. The general usefulness of the method to obtain structural long-range information in a range of several tens of angstroms is demonstrated by comparison with the peptide cluster of trichogin GA IV.
2. Acremotins A-D, peptaibiotics produced by the soil-derived fungus Acremonium persicinum SC0105
Chen Wang, Ping Wu, Lei Yao, Jinghua Xue, Liangxiong Xu, Hanxiang Li, Wangqiu Deng, Xiaoyi Wei J Antibiot (Tokyo). 2018 Nov;71(11):927-938. doi: 10.1038/s41429-018-0086-3. Epub 2018 Aug 8.
Four new peptaibiotics, acremotins A-D (1-4) featuring three α,α-dialkylated amino acid-imino acid motifs and an unreduced C-terminal residue, along with the known peptaibiotic XR586 (5) were isolated from the solid cultures of the soil-derived fungus Acremonium persicinum SC0105. Their primary structures were characterized by detailed analysis of the HRESIMS/MS fragmentation pattern combined with comprehensive interpretation of the 1D and 2D NMR spectroscopic data. The absolute configurations of amino acid residues were determined by the advanced Marfey's method. Sequence alignment result shows that 1-4 are closely related to zervamicin IIB and emerimicin IIA, thus belong to peptaibiotic subfamily-3 (SF3). The three-dimensional (3D) structure of 4 was established by theoretical conformational analysis using the ab initio density functional theory (DFT) method, which, together with the CD spectrum, indicated an amphiphilic and helical structure for 4. 1-5 actively inhibited the growth of gram-positive bacterial pathogens, and amongst them 4 was the most potent compound showing MIC of 12.5 and 6.25 µg/ml against S. aureu and MRSA strains, respectively. 1-5 were also cytotoxic against three human cancer cell lines with IC50 ranging from 1.2 to 21.6 μM.
3. Neuroleptic properties of the ion-channel-forming peptaibol zervamicin: locomotor activity and behavioral effects
Tatiana V Ovchinnikova, Natalia G Levitskaya, Olga G Voskresenskaya, Zoya A Yakimenko, Andrey A Tagaev, Anastasia Y Ovchinnikova, Arkadiy N Murashev, Andrey A Kamenskii Chem Biodivers. 2007 Jun;4(6):1374-87. doi: 10.1002/cbdv.200790117.
Zervamicins IIA and IIB are members of the peptaibol family of peptide antibiotics. They are produced by the fungus Emericellopsis salmosynnemata. Peptaibols are known to be of potential usefulness for chemotherapeutic applications, as are other secondary fungal metabolites. Previously, we have found zervamicins to decrease spontaneous locomotor activity in mice, suggesting their neurotropic properties on an equal footing with antimicrobial activity. The current study deals with behavioral effects of zervamicins IIA and IIB in mice. According to our results, both zervamicins induce a reliable decrease in locomotion and exploratory activity measured in the hole-board test. The behavioral effects of zervamicin IIA become apparent at lower dosages (0.05-2.0 mg/kg) as compared with zervamicin IIB (0.5-12.0 mg/kg). The experiments on behavioral effects in the elevated plus maze test showed that both zervamicins caused a reliable decrease in the number of head-dippings, open-arm entries, and rearings. The observed behavioral effects may be rather associated with a decrease in the exploratory activity than with anxiety-related responses in mice. Zervamicins induced depression-like behavior of experimental animals in the forced-swim test. Both peptaibols reduce physical endurance and change motor coordination of experimental animals in the bar-holding test. Taken together, the data obtained clearly indicate that both zervamicins possess neuroleptic activity.
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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 ╳
