Tautomycin
Sign in to saveTautomycin 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.
Research
205 papers- Tautomycin's interactions with protein phosphatase 1.Chemistry, an Asian journal · 2010
- Tautomycin and enzalutamide combination yields synergistic effects on castration-resistant prostate cancer.Cell death discovery · 2022
- A new antibiotic, tautomycin.The Journal of antibiotics · 1987
- Synthesis of specific protein phosphatase inhibitors, tautomycin and tautomycetin toward structure-activity relationship study.Current medicinal chemistry · 2002
- Natural products with maleic anhydride structure: nonadrides, tautomycin, chaetomellic anhydride, and other compounds.Chemical reviews · 2007
via PubMed
Wikidata facts
- Mass
- 766.450342
Show 4 more facts
- chemical formula
- C₄₁H₆₆O₁₃
- canonical SMILES
- CC1CCC2(CCC(C(O2)C(C)CCC(C(C)C(=O)CC(C(C(C(C)C)OC(=O)CC(C3=C(C(=O)OC3=O)C)O)OC)O)O)C)OC1CCC(C)C(=O)C
- isomeric SMILES
- C[C@@H]1CC[C@@]2(CC[C@@H]([C@@H](O2)[C@H](C)CC[C@@H]([C@H](C)C(=O)C[C@H]([C@H]([C@@H](C(C)C)OC(=O)C[C@H](C3=C(C(=O)OC3=O)C)O)OC)O)O)C)O[C@H]1CC[C@H](C)C(=O)C
- subject has role
- platelet aggregation inhibitors
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
2 sectionsContents
- Pharmacology
- References
{{Chembox | verifiedrevid = 470477946 | ImageFile = Tautomycin.png | ImageClass = skin-invert-image | ImageSize = | PIN = (3R,4R,5R,8S,9S,12R)-12-{(2S,3S,6R,8S,9R)-3,9-Dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl}-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoate | OtherNames = |Section1= |Section2= |Section3= }} 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. 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.
Excerpted from Wikipedia’s “Tautomycin” article, available under the CC BY-SA 4.0 licence.