Structural highlights
Function
TROPC_TALSN 2-oxoglutarate-dependent dioxygenase; part of the gene cluster that mediates the biosynthesis of the tropolone class of fungal maleic anhydrides (PubMed:22508998, PubMed:24863423). The pathway begins with the synthesis of 3-methylorcinaldehyde by the non-reducing polyketide synthase (PKS) tropA (PubMed:22508998). 3-methylorcinaldehyde is the substrate for the FAD-dependent monooxygenase tropB to yield a dearomatized hydroxycyclohexadione (PubMed:22508998, PubMed:24863423). The 2-oxoglutarate-dependent dioxygenase tropC then performs the oxidative ring expansion to provide the first tropolone metabolite stipitaldehyde (PubMed:22508998, PubMed:24863423). Trop D converts stipitaldehyde into stipitacetal which is in turn converted to stipitalide by the short-chain dehydrogenase/reductase tropE (PubMed:24863423). The next steps involve tropF, tropG, tropH, tropI and tropJ to form successive tropolone maleic anhydrides including stipitaldehydic, stipitatonic and stipitatic acids (PubMed:24863423).[1] [2]
References
- ↑ Davison J, al Fahad A, Cai M, Song Z, Yehia SY, Lazarus CM, Bailey AM, Simpson TJ, Cox RJ. Genetic, molecular, and biochemical basis of fungal tropolone biosynthesis. Proc Natl Acad Sci U S A. 2012 May 15;109(20):7642-7. PMID:22508998 doi:10.1073/pnas.1201469109
- ↑ al Fahad A, Abood A, Simpson TJ, Cox RJ. The biosynthesis and catabolism of the maleic anhydride moiety of stipitatonic acid. Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7519-23. PMID:24863423 doi:10.1002/anie.201403450
