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3-deoxyachilleol A
(+)-ambrein
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8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
squalene
8alpha-hydroxypolypoda-13,17,21-triene
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tetraprenyl-beta-curcumene + H2O
baciterpenol A
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additional information
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8alpha-hydroxypolypoda-13,17,21-triene
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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all-trans-heptaprenyl diphosphate
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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additional information
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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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8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
squalene
8alpha-hydroxypolypoda-13,17,21-triene
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?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
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?
all-trans-heptaprenyl diphosphate
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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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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metabolism
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GFPP and HexPP, the enzyme Bcl-TS substrates, are biosynthesized by enzymes E-IDS2-S/L in Bacillus clausii, and the tetraprenyl-beta-curcumene cyclase forms baciterpenol A from tetraprenyl-beta-curcumene. Proposed pathways for the biosynthesis of acyclic terpenes and menaquinones by Bacillus clausii, overview
physiological function
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the tetraprenyl-beta-curcumene synthase homologue from Bacillus clausii (Bcl-TS) catalyzes the conversion of (all-E)-geranylfarnesyl diphosphate (GFPP) and (all-E)-hexaprenyl diphosphate (HexPP) into beta-geranylfarnesene and beta-hexaprene, respectively, in vitro, and both compounds are produced in Bacillus clausii. THe enzyme is involved in the biosynthesis of menaquinones
additional information
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the ts gene or ytpB gene forms an operon with a lysophospholipase gene ytpA, which is responsible for the biosynthesis of the antibiotic bacilysocin in Bacillus subtilis
additional information
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only one sesterterpene synthase (ophiobolin F synthase, EC 4.2.3.145) that utilizes GFPP as a substrate has been identified other than Bcl-TS to date
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Sato, T.; Hoshino, H.; Yoshida, S.; Nakajima, M.; Hoshino, T.
Bifunctional triterpene/sesquarterpene cyclase: Tetraprenyl-beta-curcumene cyclase is also squalene cyclase in bacillus megaterium
J. Am. Chem. Soc.
133
17540-17543
2011
Bacillus atrophaeus (A0A0H3E5A4), Bacillus amyloliquefaciens (A0A563C0M5), Bacillus pumilus (A8FGH3), Priestia megaterium (D5DN48), Priestia megaterium (O34707), Evansella cellulosilytica (E6U1R5), Priestia megaterium 168 (O34707), Priestia megaterium 319 (D5DN48), Bacillus atrophaeus 1942 (A0A0H3E5A4)
brenda
Sato, T.; Yoshida, S.; Hoshino, H.; Tanno, M.; Nakajima, M.; Hoshino, T.
Sesquarterpenes (C35 terpenes) biosynthesized via the cyclization of a linear C35 isoprenoid by a tetraprenyl-beta-curcumene synthase and a tetraprenyl-beta-curcumene cyclase: identification of a new terpene cyclase
J. Am. Chem. Soc.
133
9734-9737
2011
Bacillus subtilis
brenda
Ueda, D.; Yamaga, H.; Murakami, M.; Totsuka, Y.; Shinada, T.; Sato, T.
Biosynthesis of sesterterpenes, head-to-tail triterpenes, and sesquarterpenes in Bacillus clausii Identification of multifunctional enzymes and analysis of isoprenoid metabolites
ChemBioChem
16
1371-1377
2015
Alkalihalobacillus clausii
brenda
Ueda, D.; Hoshino, T.; Sato, T.
Cyclization of squalene from both termini Identification of an onoceroid synthase and enzymatic synthesis of ambrein
J. Am. Chem. Soc.
135
18335-18338
2013
Priestia megaterium
brenda