) | |
| Names | |
|---|---|
| IUPAC name [(1R,2R,3R,6S,7S,10R)-10-[(2S,3S,6R,8S,9R)-3,9-Dimethyl-8-[(3S)-3-methyl-4-oxo-pentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-3,7-dihydroxy-1-isopropyl-2-methoxy-6-methyl-5-oxo-undecyl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-3-furyl)propanoate | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.149.857  |
PubChem CID | |
CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
Chemical formula | C41H66O13 |
| Molar mass | 766.966 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Tautomycin is a chemical that occurs naturally in shellfish and is produced by the bacterium Streptomyces spiroverticillatus. It is a polyketide-based structure characterized by a three hydroxyl groups, two ketones, a dialkylmaleic anhydride, an ester linkage (connecting anhydride unit to polyketide chain), a spiroketal and one methyl ether among others.
Pharmacology
It is a very potent inhibitor of the protein phosphatases PP1 and PP2A.[1] Tautomycin demonstrates a slight preference for PP1 inhibition relative to PP2A inhibition. Tautomycin is closely related to another anhydride containing polyketide PP inhibitor called tautomycetin which, in addition to being useful as a lead for cancer drug discovery, also is a very potent immunosuppressor. The mechanism of immunosuppression by Tautomycetin differs from that of more classical immunosuppressors such as rapamycin and tacrolimus.
References
- ^ Suganuma, Masami; Okabe, Sachiko; Sueoka, Eisaburo; Nishiwaki, Rie; Komori, Atsumasa; Uda, Naoto; Isono, Kiyoshi; Fujiki, Hirota (1995). "Tautomycin: An inhibitor of protein phosphatases 1 and 2A but not a tumor promoter on mouse skin and in rat glandular stomach". Journal of Cancer Research and Clinical Oncology. 121 (9–10): 621–627. doi:10.1007/bf01197780. PMID 7559747. S2CID 739519.