Ovalicin
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| Category | Antibiotics |
| Catalog number | BBF-02684 |
| CAS | 19683-98-8 |
| Molecular Weight | 296.363 |
| Molecular Formula | C16H24O5 |
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Description
Ovalicin is a natural product metobilized from the culture of fungus Pseudorotium ovalis Stolk, and it acts as an inhibitor of type 2 methionine amino-peptidase (MetAP 2). It is effective against gram-positive and gram-negative bacteria, and inhibits Mastocytoma.
Specification
| Synonyms | Ovalicin; SL-1846; SL 1846; SL1846; (-)-Ovalicin; Graphinone; (3S,4R,5S)-4-hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one |
| IUPAC Name | 4-hydroxy-5-methoxy-4-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one |
| Canonical SMILES | CC(=CCC1C(O1)(C)C2(C(C(=O)CCC23CO3)OC)O)C |
| InChI | InChI=1S/C16H24O5/c1-10(2)5-6-12-14(3,21-12)16(18)13(19-4)11(17)7-8-15(16)9-20-15/h5,12-13,18H,6-9H2,1-4H3/t12-,13-,14+,15+,16+/m1/s1 |
| InChI Key | NESRXFGQJARQNM-OWYFMNJBSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Melting Point | 89-92°C |
| Flash Point | 161.7°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. On the mode of action of the immunosuppressive sesquiterpene ovalicin
G R Hartmann, W A Zimmermann Eur J Biochem . 1981 Aug;118(1):143-50. doi: 10.1111/j.1432-1033.1981.tb05497.x.
When the potent immunosuppressive sesquiterpene ovalicin is added to lymphocyte cultures one first observes a preferential inhibition of uridine incorporation into rRNA. The uptake of the nucleoside, its conversion into the triphosphate or the polymerizing activity itself are not affected. A longer period of incubation with the drug results in a marked decrease in the number of ribosomes, with a concomitant reduction of the rate of leucine incorporation into all cellular proteins. After extended periods of time, the incorporation of thymidine into DNA in stimulated lymphocytes as well as in SV49.1 lymphoma cells is inhibited by 1 nM ovalicin or less, although part of the incorporation seems to be resistant to the drug even at much higher concentrations. A similar affect is observed with 3T6 mouse fibroblasts or HeLa cells. Here, however, a much longer incubation with the drug is required. This observation explains the selective effect of ovalicin on lymphocytes observed in vivo.
2. Syntheses of fumagillin and ovalicin
Yujiro Hayashi, Junichiro Yamaguchi Chemistry . 2010 Apr 6;16(13):3884-901. doi: 10.1002/chem.200902433.
This review focuses on the synthetic strategies used for the construction of fumagillin, ovalicin, and other natural products of this family that are known angiogenesis inhibitors. These compounds are comprised of a cyclohexane framework, two epoxides, and five or six contiguous stereogenic centers. The first total syntheses of fumagillin and ovalicin were reported by Corey in 1972 and 1985, respectively. There were numerous studies directed at these natural products in the decades that followed with many reports appearing in the year 2000 or later. Despite the relatively small size of these molecules, their syntheses highlight the efficient construction of stereogenic centers in organic synthesis.
3. Protacs: chimeric molecules that target proteins to the Skp1-Cullin-F box complex for ubiquitination and degradation
K M Sakamoto, C M Crews, K B Kim, F Mercurio, A Kumagai, R J Deshaies Proc Natl Acad Sci U S A . 2001 Jul 17;98(15):8554-9. doi: 10.1073/pnas.141230798.
The intracellular levels of many proteins are regulated by ubiquitin-dependent proteolysis. One of the best-characterized enzymes that catalyzes the attachment of ubiquitin to proteins is a ubiquitin ligase complex, Skp1-Cullin-F box complex containing Hrt1 (SCF). We sought to artificially target a protein to the SCF complex for ubiquitination and degradation. To this end, we tested methionine aminopeptidase-2 (MetAP-2), which covalently binds the angiogenesis inhibitor ovalicin. A chimeric compound, protein-targeting chimeric molecule 1 (Protac-1), was synthesized to recruit MetAP-2 to SCF. One domain of Protac-1 contains the I kappa B alpha phosphopeptide that is recognized by the F-box protein beta-TRCP, whereas the other domain is composed of ovalicin. We show that MetAP-2 can be tethered to SCF(beta-TRCP), ubiquitinated, and degraded in a Protac-1-dependent manner. In the future, this approach may be useful for conditional inactivation of proteins, and for targeting disease-causing proteins for destruction.
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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 ╳
