The enzyme is involved in the biosynthesis of the phytotoxin solanapyrone in some fungi. The bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent Diels Alder cycloisomerization of the product prosolanapyrone III to (-)-solanapyrone A (cf. EC 1.1.3.42, prosolanapyrone II oxidase).
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
the Diels-Alder reaction is a [4+2] cycloaddition reaction in which a cyclohexene ring is formed between a 1,3-diene and an electron-deficient alkene via a single pericyclic transition state
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SYSTEMATIC NAME
IUBMB Comments
prosolanapyrone-III:(-)-solanapyrone A isomerase
The enzyme is involved in the biosynthesis of the phytotoxin solanapyrone in some fungi. The bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent Diels Alder cycloisomerization of the product prosolanapyrone III to (-)-solanapyrone A (cf. EC 1.1.3.42, prosolanapyrone II oxidase).
via intermediate 6, the SpnF-catalysed endomode syn-addition of an alkenyl to a dienyl functionality seems consistent with a Diels-Alder reaction, but a stepwise [4+2] cycloaddition mechanism, for example, one involving a dipolar intermediate such as 7, cannot be ruled out
the bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent cycloaddition of the product prosolanapyrone III to (-)-solanapyrone A
the bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent cycloaddition of the product prosolanapyrone III to (-)-solanapyrone A
in an enzyme-catalyzed DielsAlder reaction the product prosolanapyrone III is isomerized to solanapyrone A (exo Diels-Alder cyclization, [4+2] cycloaddition). Solanapyrone D (endo Diels-Alder cyclization) is formed by a nonenzymatic Diels-Alder cyclization of prosolanopyrone III in polar solvents. The enzyme coverts prosolanapyrone II into solanapyrone A, solanapyrone D and prosolanapyrone III in the ratio 7:1:1
the bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent cycloaddition of the product prosolanapyrone III to (-)-solanapyrone A. Prosolanapyrone III is isomerized to solanapyrone A (exo Diels-Alder cyclization, [4+2] cycloaddition). Solanapyrone D (endo Diels-Alder cyclization) is formed by a nonenzymatic Diels-Alder cyclization of prosolanopyrone III in polar solvents. The enzyme coverts prosolanapyrone II into solanapyrone A, solanapyrone D and prosolanapyrone III in the ratio 7:1:1
the bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent cycloaddition of the product prosolanapyrone III to (-)-solanapyrone A. Prosolanapyrone III is isomerized to solanapyrone A (exo Diels-Alder cyclization, [4+2] cycloaddition). Solanapyrone D (endo Diels-Alder cyclization) is formed by a nonenzymatic Diels-Alder cyclization of prosolanopyrone III in polar solvents. The enzyme coverts prosolanapyrone II into solanapyrone A, solanapyrone D and prosolanapyrone III in the ratio 7:1:1
SpnF specifically accelerates the ring formation reaction with an estimated 500fold rate enhancement. The cyclization event is modelled as the sum of a first order and a Michaelis-Menten process and fits
the Diels-Alder reaction is the key transformation in the biosynthesis of many cyclohexene-containing secondary metabolites. Cyclase SpnF catalyses a transannular [4+2] cycloaddition to form the cyclohexene ring in spinosyn A, it catalyzes the cyclization step of macrolactone
Solanapyrone synthase, a possible Diels-Alderase and iterative type I polyketide synthase encoded in a biosynthetic gene cluster from Alternaria solani