5.5.1.20: prosolanapyrone-III cycloisomerase
This is an abbreviated version!
For detailed information about prosolanapyrone-III cycloisomerase, go to the full flat file.
Reaction
Synonyms
PKS10-2, Sol5, solanapyrone polyketide synthase, solanapyrone synthase, SpnF, SPS
ECTree
5.5.1.20 prosolanapyrone-III cycloisomeraseAdvanced search results
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results (Substrates Products
Substrates Products on EC 5.5.1.20 - prosolanapyrone-III cycloisomerase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3E,5E,7E,10R,12E,14E,17R,18S,22S)-22-ethyl-10,18-dihydroxy-17-methyloxacyclodocosa-3,5,7,12,14-pentaene-2,16-dione
(2R,3aS,5aS,6E,10S,14S,15R,17E,18aS,18bR)-10-ethyl-2,14-dihydroxy-15-methyl-2,3,3a,5a,10,11,12,13,14,15,18a,18b-dodecahydro-1H-indeno[5,4-e]oxacyclopentadecine-8,16-dione
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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
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?
additional information
?
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mode of formation of the complex perhydro-as-indacene moiety in spinosyn A, overview. No activity with keto-intermediate 3
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?
prosolanapyrone III
(-)-solanapyrone A
the enzyme is involved in solanapyrone biosynthesis
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?
prosolanapyrone III
(-)-solanapyrone A
the bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent cycloaddition of the product prosolanapyrone III to (-)-solanapyrone A
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-
?
prosolanapyrone III
(-)-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
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?
prosolanapyrone III
(-)-solanapyrone A
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
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?
prosolanapyrone III
(-)-solanapyrone A
the enzyme is involved in solanapyrone biosynthesis
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?
prosolanapyrone III
(-)-solanapyrone A
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
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?
