4.2.3.130: tetraprenyl-beta-curcumene synthase
This is an abbreviated version!
For detailed information about tetraprenyl-beta-curcumene synthase, go to the full flat file.
Reaction
Synonyms
Bcl-TS, BmeTC, More, sesterterpene/triterpene/sesquarterpene synthase, tetraprenyl-beta-curcumene cyclase, ytpB
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.130 - tetraprenyl-beta-curcumene synthase
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REACTION DIAGRAM
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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the BmeTC-catalyzed reaction of the substrate is initiated by the protonation of a terminal isopropylidene moiety, triggering a series of cyclization events, erminated by the nucleophilic addition of a hydroxyl group or the deprotonation of H-26 at the resulting C-8 carbocation, respectively
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tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A563C0M5
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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tetraprenyl-beta-curcumene shows nonenzymatic autooxidation to tetraprenyl-alpha-curcumene
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
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Bcl-TS is a sesterterpene (C25)/triterpene (C30) synthase, the enzyme catalyzes the conversion of (all-E)-geranylfarnesyl diphosphate (GFPP) and (all-E)-hexaprenyl diphosphate (HexPP) into beta-geranylfarnesene and beta-hexaprene in a head-to-tail triterpene synthase. NMR spectroscopic and TLC analysis of radiolabeled products, overview. Enzyme Bcl-TS can accept HepPP (C35) as a substrate and cyclizes HepPP (C35) to a monocycle
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additional information
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onoceroids are synthesized from squalene via an intermediate cyclized from one terminus, such as 8alpha-hydroxypolypoda-13,17,21-triene, by cyclization at both termini. Enzyme BmeTC may have single active site: it starts with the initial cascade leading to the bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene from squalene, then turns molecule 8alpha-hydroxypolypoda-13,17,21-triene outside of the active site cavity, and again uptake 8alpha-hydroxypolypoda-13,17,21-triene to catalyze the formation of additional bicyclic and tricyclic structures of onoceranoxide and 14beta-hydroxyonocera-8(26)-ene on the other side of 8alpha-hydroxypolypoda-13,17,21-triene. BmeTC is not only a bifunctional terpene cyclase which converts tetraprenyl-beta-curcumene and squalene into baciterpenol A and 8alpha-hydroxypolypoda-13,17,21-triene but also an onoceroid synthase that catalyzes the convertion of 8alpha-hydroxypolypoda-13,17,21-triene into onoceranoxide and 14beta-hydroxyonocera-8(26)-ene. GC-MS product analysis, overview
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