Oligomycin C
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| Category | Antibiotics |
| Catalog number | BBF-02620 |
| CAS | 11052-72-5 |
| Molecular Weight | 775.06 |
| Molecular Formula | C45H74O10 |
| Purity | >95% by HPLC |
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Description
A minor component of the oligomycin complex isolated from selected strains of streptomyces; an inhibitor of mitochondrial F1F0-atpas; used as an eukaryotic ATP synthase inhibitor, induces apoptosis.
Specification
| Synonyms | 12-Deoxyoligomycin A |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4E,5'R,6R,6'R,7S,8R,10S,11R,12R,14R,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,15-trihydroxy-6'-[(2S)-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]-3,9,13-trione |
| Canonical SMILES | CCC1CCC2C(C(C(C3(O2)CCC(C(O3)CC(C)O)C)C)OC(=O)C=CC(C(C(C(=O)C(C(C(C(=O)C(C(C(CC=CC=C1)C)O)C)C)O)C)C)O)C)C |
| InChI | InChI=1S/C45H74O10/c1-12-35-17-15-13-14-16-26(3)39(48)30(7)41(50)32(9)43(52)33(10)42(51)31(8)40(49)27(4)18-21-38(47)53-44-29(6)36(20-19-35)54-45(34(44)11)23-22-25(2)37(55-45)24-28(5)46/h13-15,17-18,21,25-37,39-40,43-44,46,48-49,52H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26+,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,39-,40+,43-,44+,45-/m1/s1 |
| InChI Key | CMMLZMMKTYEOKV-JEKNLLRFSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Cylindrical Crystals |
| Antibiotic Activity Spectrum | fungi; neoplastics (Tumor) |
| Boiling Point | 876.2°C at 760 mmHg |
| Melting Point | 198-200°C |
| Density | 1.12 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1.Total synthesis of rutamycin B and oligomycin C.
Panek JS1, Jain NF. J Org Chem. 2001 Apr 20;66(8):2747-56.
The asymmetric synthesis of the macrolide antibiotics (+)-rutamycin B (1) and (+)-oligomycin C (2) is described. The approach relied on the synthesis and coupling of the individual spiroketal fragments 3a and 3b with the C1-C17 polyproprionate fragment 4. The preparation of the spiroketal fragments was achieved using chiral (E)-crotylsilane bond construction methodology, which allowed the introduction of the stereogenic centers prior to spiroketalization. The present work details the synthesis of the C19-C28 and C29-C34 subunits as well as their convergent assembly through an alkylation reaction of the lithiated N,N-dimethylhydrazones 6 and 8 to afford the individual linear spiroketal intermediates 5a and 5b, respectively. After functional group adjustment, these advanced intermediates were cyclized to their respective spiroketal-coupling partners 40 and 41. The requisite polypropionate fragment was assembled in a convergent manner using asymmetric crotylation methodology for the introduction of six of the nine-stereogenic centers.
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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 ╳
