Ossamycin
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| Category | Antibiotics |
| Catalog number | BBF-02323 |
| CAS | 11015-84-2 |
| Molecular Weight | 912.20 |
| Molecular Formula | C49H85NO14 |
| Purity | ≥98% |
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Description
Ossamycin is a macrolide antibiotic produced by the strain of Str. hygroscopicus, Var. ossamyceticus C 8158. It has anti-fungal effect, and it has weaker anti-gram-positive bacterial effect. It inhibits L cells, Epstein-Barr ascites cancer cells, KB cells, sarcoma-180 cells, L-1210 cells, HeLa cells in cell culture with IC50s (μg/mL) of 0.007, 0.008, 0.005, 0.008, 0.003, 0.005, respectively. It has no antitumor effect in in vivo animal test.
Specification
| Synonyms | Antibiotic NK 154183B |
| IUPAC Name | (1S,3S,6'R,7S,8E,15R,16R,17S,18R,19R,20S,21R,22E,26S,28R,30R)-17-[(2S,5S,6S)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-3,15,16,18,20,21-hexahydroxy-6'-[(2R)-2-hydroxybutyl]-5,5,15,19,21,30-hexamethylspiro[4,25,29-trioxatricyclo[24.3.1.03,7]triaconta-8,22-diene-28,2'-oxane]-24-one |
| Canonical SMILES | CCC(CC1CCCC2(O1)CC3C(C(O2)CC4(C(CC(O4)(C)C)C=CCCCCCC(C(C(C(C(C(C(C=CC(=O)O3)(C)O)O)C)O)OC5CCC(C(O5)C)N(C)C)O)(C)O)O)C)O |
| InChI | InChI=1S/C49H85NO14/c1-11-34(51)26-35-19-17-24-48(62-35)28-37-30(2)38(63-48)29-49(58)33(27-45(5,6)64-49)18-15-13-12-14-16-23-46(7,56)44(55)42(61-40-21-20-36(50(9)10)32(4)59-40)41(53)31(3)43(54)47(8,57)25-22-39(52)60-37/h15,18,22,25,30-38,40-44,51,53-58H,11-14,16-17,19-21,23-24,26-29H2,1-10H3/b18-15+,25-22+/t30-,31+,32-,33+,34+,35+,36-,37-,38-,40-,41+,42-,43-,44+,46+,47+,48+,49-/m0/s1 |
| InChI Key | XGECDDPXIKFBTE-AUFVQPSPSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Melting Point | 185-187°C |
| Solubility | Soluble in Chloroform, Ethanol, Methanol, Ethyl Acetate, Acetone |
Reference Reading
1. Enzyme-Catalyzed Spiroacetal Formation in Polyketide Antibiotic Biosynthesis
Oksana Bilyk, Gabriel S Oliveira, Rafaela M de Angelo, Michell O Almeida, Kathia Maria Honório, Finian J Leeper, Marcio V B Dias, Peter F Leadlay J Am Chem Soc. 2022 Aug 17;144(32):14555-14563. doi: 10.1021/jacs.2c03313. Epub 2022 Aug 3.
A key step in the biosynthesis of numerous polyketides is the stereospecific formation of a spiroacetal (spiroketal). We report here that spiroacetal formation in the biosynthesis of the macrocyclic polyketides ossamycin and oligomycin involves catalysis by a novel spiroacetal cyclase. OssO from the ossamycin biosynthetic gene cluster (BGC) is homologous to OlmO, the product of an unannotated gene from the oligomycin BGC. The deletion of olmO abolished oligomycin production and led to the isolation of oligomycin-like metabolites lacking the spiroacetal structure. Purified OlmO catalyzed complete conversion of the major metabolite into oligomycin C. Crystal structures of OssO and OlmO reveal an unusual 10-strand β-barrel. Three conserved polar residues are clustered together in the β-barrel cavity, and site-specific mutation of any of these residues either abolished or substantially diminished OlmO activity, supporting a role for general acid/general base catalysis in spiroacetal formation.
2. Discovery of novel natural products for mosquito control
Cecilia S Engdahl, Chinmay V Tikhe, George Dimopoulos Parasit Vectors. 2022 Dec 21;15(1):481. doi: 10.1186/s13071-022-05594-z.
Vector control plays a key role in reducing the public health burden of mosquito-borne diseases. Today's vector control strategies largely rely on synthetic insecticides that can have a negative environmental impact when applied outdoors and often become inefficient because of the mosquitoes' ability to develop resistance. An alternative and promising approach to circumvent these challenges involves the implementation of insecticides derived from nature (biopesticides) for vector control. Biopesticides can constitute naturally occurring organisms or substances derived from them that have lifespan-shortening effects on disease vectors such as mosquitoes. Here we present the discovery and evaluation of natural product-based biological control agents that can potentially be developed into biopesticides for mosquito control. We screened a natural product collection comprising 390 compounds and initially identified 26 molecules with potential ability to kill the larval stages of the yellow fever mosquito Aedes aegypti, which is responsible for transmitting viruses such as dengue, Zika, chikungunya and yellow fever. Natural products identified as hits in the screen were further evaluated for their suitability for biopesticide development. We show that a selection of the natural product top hits, bactobolin, maytansine and ossamycin, also killed the larval stages of the malaria-transmitting mosquito Anopheles gambiae as well as the adult form of both species. We have further explored the usefulness of crude extracts and preparations from two of the best candidates' sources (organisms of origin) for mosquitocidal activity, that is extracts from the two bacteria Burkholderia thailandensis and Streptomyces hygroscopicus var. ossamyceticus.
3. The biosynthetic pathway to ossamycin, a macrocyclic polyketide bearing a spiroacetal moiety
Oksana Bilyk, Markiyan Samborskyy, Peter F Leadlay PLoS One. 2019 Apr 30;14(4):e0215958. doi: 10.1371/journal.pone.0215958. eCollection 2019.
Ossamycin from Streptomyces hygroscopicus var. ossamyceticus is an antifungal and cytotoxic polyketide and a potent inhibitor of the mitochondrial ATPase. Analysis of a near-complete genome sequence of the ossamycin producer has allowed the identification of the 127-kbp ossamycin biosynthetic gene cluster. The presence in the cluster of a specific crotonyl-CoA carboxylase/reductase homologue suggests that the 5-methylhexanoate extension unit used in construction of the macrocyclic core is incorporated intact from the unusual precursor isobutyrylmalonyl-CoA. Surprisingly, the modular polyketide synthase uses only 14 extension modules to accomplish 15 cycles of polyketide chain extension, a rare example of programmed iteration on a modular polyketide synthase. Specific deletion of genes encoding cytochrome P450 enzymes has given insight into the late-stage tailoring of the ossamycin macrocycle required for the attachment of the unusual 2,3,4,6-deoxyaminohexose sugar l-ossamine to C-8 of the ossamycin macrocycle. The ossamycin cluster also encodes a putative spirocyclase enzyme, OssO, which may play a role in establishing the characteristic spiroketal moiety of the natural product.
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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 ╳
