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Information on EC 4.2.3.130 - tetraprenyl-beta-curcumene synthase
for references in articles please use BRENDA:EC4.2.3.130
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EC Tree 4 Lyases
4.2 Carbon-oxygen lyases
4.2.3 Acting on phosphates
4.2.3.130 tetraprenyl-beta-curcumene synthase
IUBMB Comments
Isolated from Bacillus subtilis. This sesquarterpene is present in a number of Bacillus species.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
showSynonyms
bmetc, sesterterpene/triterpene/sesquarterpene synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ytpB
ytpB
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
all-trans-heptaprenyl diphosphate = tetraprenyl-beta-curcumene + diphosphate
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-
-
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SYSTEMATIC NAME
IUBMB Comments
all-trans-heptaprenyl-diphosphate diphosphate-lyase (cyclizing, tetraprenyl-beta-curcumene-forming)
Isolated from Bacillus subtilis. This sesquarterpene is present in a number of Bacillus species.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-deoxyachilleol A
(+)-ambrein
-
Substrates: -
Products: -
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?
squalene
8alpha-hydroxypolypoda-13,17,21-triene
-
Substrates: -
Products: -
Products: -
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
-
Substrates: -
Products: -
Products: -
?
8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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Substrates: -
Products: -
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8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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Substrates: 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
Products: -
Products: -
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8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A563C0M5
Substrates: -
Products: -
Products: -
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all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A0H3E5A4
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A0H3E5A4
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
-
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
-
Substrates: -
Products: tetraprenyl-beta-curcumene shows nonenzymatic autooxidation to tetraprenyl-alpha-curcumene
Products: tetraprenyl-beta-curcumene shows nonenzymatic autooxidation to tetraprenyl-alpha-curcumene
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
-
Substrates: -
Products: -
Products: -
?
additional information
?
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Substrates: 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
Products: -
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additional information
?
-
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Substrates: 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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Products: -
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
Substrates: -
Products: -
Products: -
?
squalene
8alpha-hydroxypolypoda-13,17,21-triene
-
Substrates: -
Products: -
Products: -
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
-
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A563C0M5
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A0H3E5A4
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
A0A0H3E5A4
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
-
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
Substrates: -
Products: -
Products: -
?
all-trans-heptaprenyl diphosphate
tetraprenyl-beta-curcumene + diphosphate
-
Substrates: -
Products: -
Products: -
?
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
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
-
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
additional information
-
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
-
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). D5DN48_PRIM3
Priestia megaterium (strain DSM 319 / IMG 1521)
352
0
41157
TrEMBL
-
E6U1R5_EVAC2
Evansella cellulosilytica (strain ATCC 21833 / DSM 2522 / FERM P-1141 / JCM 9156 / N-4)
353
0
41621
TrEMBL
other Location (Reliability: 5)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D377C
D377C
-
mutant produces 3-deoxyachilleol and 8alpha-hydroxypolypoda-13,17,21-triene while 14beta-hydroxyonocera-8(26)-ene and onoceranoxide are below detection limit. A Pichia pastoris strain expressing the mutant produces more (+)-ambrein, i.e. 15 mg/l in shake flask cultivation, than coexpression of Alicyclobacillus acidocaldarius squalene-hopene cyclase mutant D377C and tetraprenyl-beta-curcumene cyclase wild-type
D377C
-
mutant is able to catalyze the conversions from squalene to the intermediate 3-deoxyachilleol and further (+)-ambrein more efficiently than wild-type
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant fusion protein YtpB from Escherichia coli strain BL21(DE3) by affinity chromatography
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene ytpB, expression as fusion protein in Escherichia coli strain BL21(DE3) from pColdTF. 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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
production of ambrein in Pichia pastoris. Intracellular levels of the precursor squalene are significantly enhanced by reducing its flux towards ergosterol biosynthesis, and the enzyme cascade of Alicyclobacillus acidocaldarius squalene-hopene cyclase mutant D377C and tetraprenyl-beta-curcumene cyclase from Bacillus megaterium are heterologously expressed. Besides, use of tetraprenyl-beta-curcumene cyclase mutant D377C leads to a one-enzyme system by far superior to the cascade, increasing (+)-ambrein levels approximately 7fold in shake flask cultivation. Upscaling to 5 l bioreactor yields more than 100 mg/l of (+)-ambrein
synthesis
-
expression of mutant D377C in Saccharomyces cerevisiae with enhanced intracellular supply of squalene by overexpression of the N-terminally truncated 3-hydroxy-3-methylglutaryl-CoA reductase 1 (tHMG) and the squalene synthase (ERG9), results in production of squalene, 3-deoxyachillol and (+)-ambrein
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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 amyloliquefaciens (A0A563C0M5), Bacillus atrophaeus (A0A0H3E5A4), Bacillus atrophaeus 1942 (A0A0H3E5A4), Bacillus pumilus (A8FGH3), Evansella cellulosilytica (E6U1R5), Priestia megaterium (O34707), Priestia megaterium (D5DN48), Priestia megaterium 168 (O34707), Priestia megaterium 319 (D5DN48)
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.; 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
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
Shouchella clausii
brenda
Moser, S.; Strohmeier, G.A.; Leitner, E.; Plocek, T.J.; Vanhessche, K.; Pichler, H.
Whole-cell (+)-ambrein production in the yeast Pichia pastoris
Metab. Eng. Commun.
7
e00077
2018
Priestia megaterium
brenda
Moser, S.; Leitner, E.; Plocek, T.J.; Vanhessche, K.; Pichler, H.
Engineering of Saccharomyces cerevisiae for the production of (+)-ambrein
Yeast
37
163-172
2020
Priestia megaterium
brenda
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