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 3 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
Sources (2)
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Article
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.