Oligomycin E
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| Category | Bioactive by-products |
| Catalog number | BBF-04283 |
| CAS | 110231-34-0 |
| Molecular Weight | 821.05 |
| Molecular Formula | C45H72O13 |
| Purity | >95% by HPLC |
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Description
It is a minor metabolite from the oligomycin complex produced by several species of streptomyces. It exhibits weak antibacterial activity and is considerably weaker as an antifungal agent.
Specification
| Synonyms | (1R,2'S,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28R,29R)-22-ethyl-5',6'-dihydro-7,11,14,15,28-pentahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,3',9,13(4'H)-tetrone; 26-hydroxy-28-oxo-Oligomycin A; [1R-[1R*,4E,5'S*,6S*,6'S*(R*),7R*,8S*,10R*,11R*,12S*,14R*,15S*,16R*,18E,20E,22R*,25S*,27S*,28R*,29R*]]-22-Ethyl-5',6'-dihydro-7,11,14,15,28-pentahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,3',9,13(4'H)-tetrone |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27S,28R,29R)-22-ethyl-7,11,14,15,28-pentahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,3',9,13-tetrone |
| Canonical SMILES | CCC1CCC2C(C(C(C3(O2)C(=O)CC(C(O3)CC(C)O)C)(C)O)OC(=O)C=CC(C(C(C(=O)C(C(C(C(=O)C(C(C(CC=CC=C1)C)O)(C)O)C)O)C)C)O)C)C |
| InChI | InChI=1S/C45H72O13/c1-12-32-17-15-13-14-16-25(3)40(52)43(10,54)41(53)31(9)39(51)30(8)38(50)29(7)37(49)24(2)18-21-36(48)56-42-28(6)33(20-19-32)57-45(44(42,11)55)35(47)22-26(4)34(58-45)23-27(5)46/h13-15,17-18,21,24-34,37,39-40,42,46,49,51-52,54-55H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,37+,39+,40-,42+,43+,44+,45-/m0/s1 |
| InChI Key | UWEZMQMMPORRMH-BOCHHXLBSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Lyophilisate |
| Antibiotic Activity Spectrum | Fungi; Bacterial |
| Boiling Point | 940.6±65.0°C (Predicted) |
| Density | 1.20±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Rapid kinetic analyses of the Na+/K(+)-ATPase distinguish among different criteria for conformational change
J D Robinson, P R Pratap Biochim Biophys Acta . 1993 Sep 5;1151(1):89-98. doi: 10.1016/0005-2736(93)90075-b.
The Na+/K(+)-ATPase couples the hydrolysis of ATP to the transport of Na+ and K+ via a phosphorylated intermediate and conformational changes. In order to identify these conformational changes, we have probed the sequence of steps from EP(3Na+ in) to EP + 3Na+ out with three fluorescent probes (IAF: 5-iodoacetamidofluorescein; BIPM: N-[p-(2-benzimidazolyl)phenyl]maleimide; and RH421) and the sensitivity of their fluorescence change to oligomycin and divalent cations (Ca2+ and Mn2+). The magnitude (% delta F) and rate constant (k(obs)) of ATP-induced fluorescence changes were measured on a fluorescence stopped-flow apparatus, and yielded the following results. (a) With RH421, k(obs) and % delta F varied with [Na+] (maximal k(obs) = 100 s-1, K1/2 = 6 mM; % delta Fmax = 6%, K1/2 = 1 mM); these values are comparable to those previously reported using IAF-labeled enzyme (Pratap, P.R., Robinson, J.D. and Steinberg, M.I. (1991) Biochim. Biophys. Acta 1069, 288-298). (b) With BIPM-labeled enzyme k(obs) did not vary with [Na+] over the range tested, and was twice as high as the maximum k(obs) for RH421. (c) Treatment with oligomycin reduced k(obs) for all three probes to about the same level (approximately 1-2 s-1) while % delta Fmax was largely unaffected. (d) Replacing Mg2+ with Ca2+ had similar effects to treatment with oligomycin. (e) RH421 fluorescence change was completely abolished in the presence of oligomycin and Ca2+. (f) Replacing Mg2+ with Mn2+ decreased IAF fluorescence, i.e., put the enzyme in an E2-like form, reduced k(obs), and rendered oligomycin less effective in reducing k(obs). From these results, we conclude: (a) the release of the second/third Na+ is the rate-limiting step for the conformational change measured by IAF and charge transfer measured with RH421; (b) BIPM indicates an earlier step, either the deocclusion of Na+ and/or the release of the first Na+; (c) oligomycin blocks Na+ deocclusion, and this step is sensitive to the divalent cation used to activate enzyme phosphorylation; and (d) Ca2+ slows the step reported by IAF as well. These experiments indicate that a simple model with two conformations (E1 and E2) is insufficient to explain transient kinetic data.
2. Oligomycins A and E, major bioactive secondary metabolites produced by Streptomyces sp. strain HG29 isolated from a Saharan soil
N Bouras, H-P Klenk, H Boudjella, F Pont, F Mathieu, N Sabaou, C Bijani, N Khebizi J Mycol Med . 2018 Mar;28(1):150-160. doi: 10.1016/j.mycmed.2017.10.007.
An actinobacterial strain, HG29, with potent activity against pathogenic, toxigenic and phytopathogenic fungi was isolated from a Saharan soil sample of Algeria. On the basis of morphological and chemotaxonomic characteristics, the strain was classified in the genus Streptomyces. Analysis of the 16S rRNA gene sequence showed a similarity level of 99.3% with Streptomyces gancidicus NBRC 15412T. The comparison of its cultural and physiological characteristics with this species revealed significant differences. Moreover, the phylogenetic tree showed that strain HG29 forms a distinct phyletic line within the genus Streptomyces. Production of antifungal activity was investigated by following kinetics in shake broth. The highest antifungal activity was obtained after five days of fermentation, and in the dichloromethane extract. Two active compounds, NK1 and NK2, were purified by HPLC using a C18 column. Their chemical structures were identified through nuclear magnetic resonance experiments and mass spectrometry as oligomycins E and A, respectively, which have not been reported to be produced by S. gancidicus. The two bioactive compounds exhibited significant antifungal activity in vitro, showing minimal inhibitory concentrations (MICs) values between 2 and 75μg/mL.
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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 ╳
