Tautomycin is a chemical that occurs naturally in
shellfish
Shellfish is a colloquial and fisheries term for exoskeleton-bearing aquatic invertebrates used as food, including various species of molluscs, crustaceans, and echinoderms. Although most kinds of shellfish are harvested from saltwater envir ...
and is produced by the bacterium ''
Streptomyces spiroverticillatus''. It is a
polyketide-based structure characterized by a three
hydroxyl groups, two
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
s, a dialkylmaleic anhydride, an
ester linkage (connecting anhydride unit to polyketide chain), a spiroketal and one
methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
ether among others.
Pharmacology
It is a very potent inhibitor of the protein
phosphatase
In biochemistry, a phosphatase is an enzyme that uses water to cleave a phosphoric acid Ester, monoester into a phosphate ion and an Alcohol (chemistry), alcohol. Because a phosphatase enzyme catalysis, catalyzes the hydrolysis of its Substrate ...
s 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.
References
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Phosphatase inhibitors
Polyketides
Spiro compounds