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(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (2S,3R,6S,9S)-(-)-protoillud-7-ene-forming)
The enzyme has been described from the slime-mould Dictyostelium discoideum. It is specific for (2E,6E)-farnesyl diphosphate. While the major product is the sequiterpene (2S,3R,6S,9S)-(-)-protoillud-7-ene, traces of pentalenene are also formed.
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-protoillud-7-ene + diphosphate
Substrates: -
Products: -
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additional information
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Substrates: no substrates: geranyl diphosphate and geranylgeranyl diphosphate
Products: -
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
Substrates: one possible function of volatile terpenes emitted from Dictyostelium discoideum is to attract other organisms to facilitate spore dispersal, resembling the function of volatile terpenes from the fruiting bodies of fungi
Products: -
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
Substrates: -
Products: (2S,3R,6S,9S)-(-)-protoillud-7-ene i.e. (2aS,4aS,7aS,7bR)-3,6,6,7b-tetramethyl-2,2a,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]indene
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
Substrates: no activity with geranyl diphosphate and geranylgeranyl diphosphate. The biosynthesis of (2S,3R,6S,9S)-(-)-protoillud-7-ene starts by 1,11-cyclization of (2E,6E)-farnesyl diphosphate to the humulyl cation. A 1,2-hydride shift and cyclization furnishes the protoilludyl cation that yields (2S,3R,6S,9S)-(-)-protoillud-7-ene upon deprotonation, while pentalenene is formed by dyotropic rearrangement and deprotonation
Products: the major product is the sequiterpene (2S,3R,6S,9S)-()-protoillud-7-ene. Traces of pentalenene are also formed. (2S,3R,6S,9S)-()-protoillud-7-ene i.e. (2aS,4aS,7aS,7bR)-3,6,6,7b-tetramethyl-2,2a,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]indene
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
Substrates: one possible function of volatile terpenes emitted from Dictyostelium discoideum is to attract other organisms to facilitate spore dispersal, resembling the function of volatile terpenes from the fruiting bodies of fungi
Products: -
?
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Rabe, P.; Rinkel, J.; Nubbemeyer, B.; Kollner, T.G.; Chen, F.; Dickschat, J.S.
Terpene cyclases from social amoebae
Angew. Chem. Int. Ed. Engl.
55
15420-15423
2016
Dictyostelium discoideum (Q54P86)
brenda
Chen, X.; Kollner, T.G.; Jia, Q.; Norris, A.; Santhanam, B.; Rabe, P.; Dickschat, J.S.; Shaulsky, G.; Gershenzon, J.; Chen, F.
Terpene synthase genes in eukaryotes beyond plants and fungi: occurrence in social amoebae
Proc. Natl. Acad. Sci. USA
113
12132-12137
2016
Dictyostelium discoideum (Q54P86)
brenda
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