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Information on EC 4.2.1.137 - sporulenol synthase
for references in articles please use BRENDA:EC4.2.1.137
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IUBMB Comments
The reaction occurs in the reverse direction. Isolated from Bacillus subtilis. Similar sesquarterpenoids are present in a number of Bacillus species.
The enzyme appears in viruses and cellular organisms
showSynonyms
sqhC, tetraprenyl-beta-curcumene cyclase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
sqhC
tetraprenyl-beta-curcumene cyclase
sqhC
-
-
-
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tetraprenyl-beta-curcumene cyclase
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bifunctional enzyme, cyclizing both tetraprenyl-beta-curcumene and squalene in vivo
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sporulenol = tetraprenyl-beta-curcumene + H2O
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-
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SYSTEMATIC NAME
IUBMB Comments
tetraprenyl-beta-curcumene-sporulenol cyclase
The reaction occurs in the reverse direction. Isolated from Bacillus subtilis. Similar sesquarterpenoids are 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
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
beta-hexaprene
?
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Substrates: substrate specificity, overview. Enzymatic cyclization of head-to-tail acyclic triterpene beta-hexaprene, a natural product isolated from Bacillus clausii, by tetraprenyl-beta-curcumene cyclase from Bacillus subtilis results in the formation of two unnatural pentacyclic triterpenes. The enzyme can be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of the enzyme has sufficient space to accommodate this unnatural pentacyclic scaffold
Products: -
Products: -
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beta-hexaprene
?
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Substrates: substrate specificity, overview. Enzymatic cyclization of head-to-tail acyclic triterpene beta-hexaprene, a natural product isolated from Bacillus clausii, by tetraprenyl-beta-curcumene cyclase from Bacillus subtilis results in the formation of two unnatural pentacyclic triterpenes. The enzyme can be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of the enzyme has sufficient space to accommodate this unnatural pentacyclic scaffold
Products: -
Products: -
?
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: -
Products: -
?
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: the product is further converted by nonenzymatic autoxidation and thermal dehydration, overview
Products: the product is further converted by nonenzymatic autoxidation and thermal dehydration, overview
?
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: -
Products: -
?
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: the product is further converted by nonenzymatic autoxidation and thermal dehydration, overview
Products: the product is further converted by nonenzymatic autoxidation and thermal dehydration, overview
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
-
Substrates: -
Products: -
Products: -
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
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Substrates: -
Products: -
Products: -
?
additional information
?
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Substrates: the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
Products: -
Products: -
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additional information
?
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Substrates: it is demonstrated that a tetraprenyl-beta-curcumene cyclase also cyclizes a tail-to-tail type of linear squalene into a bicyclic triterpenol, 8alpha-hydroxypolypoda-13,17,21-triene
Products: -
Products: -
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additional information
?
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-
Substrates: the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
Products: -
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
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: -
Products: -
?
tetraprenyl-alpha-curcumene + H2O
(1R,2R,4aS,4bR,6aS,10aS,10bR,12aS)-2,4b,7,7,10a,12a-hexamethyl-1-[(3R)-3-(4-methylphenyl)butyl]octadecahydrochrysen-2-ol
Substrates: -
Products: -
Products: -
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
-
Substrates: -
Products: -
Products: -
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
Products: -
Products: -
?
additional information
?
-
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Substrates: the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
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
evolution
metabolism
evolution
tetraprenyl-beta-curcumene cyclase shows no sequence homology to any of the known terpene cyclases
evolution
-
tetraprenyl-beta-curcumene cyclase shows no sequence homology to any of the known terpene cyclases
-
metabolism
-
tetraprenyl-beta-curcumene cyclase is bifunctional, cyclizing both tetraprenyl-beta-curcumene and squalene in vivo
metabolism
the enzyme is involved in biosynthesis of terpenes of the distinct family of sesquarterpenes, that are mono- and pentacyclic C35 terpenes biosynthesized via the cyclization of C35 isoprenoid, overview
metabolism
-
the enzyme is involved in biosynthetic pathway of sesquarterpenes (C35) and triterpenes (C30), overview
metabolism
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the enzyme is involved in biosynthetic pathway of sesquarterpenes (C35), overview
metabolism
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the enzyme is involved in biosynthesis of terpenes of the distinct family of sesquarterpenes, that are mono- and pentacyclic C35 terpenes biosynthesized via the cyclization of C35 isoprenoid, overview
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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). A0A5J4PX01_9ZZZZ
386
2
42424
TrEMBL
other Location (Reliability: 3)
A0A5J4RQ32_9ZZZZ
567
0
62655
TrEMBL
other Location (Reliability: 2)
A0A517NRF7_9BACT
660
0
72517
TrEMBL
-
A0A7V9Z8V0_9BACI
629
0
71996
TrEMBL
-
A0A8F5CAJ5_9BACI
625
0
70861
TrEMBL
-
A0A6H0H321_BACIU
632
0
71224
TrEMBL
-
I3E8W8_BACMM
Bacillus methanolicus (strain MGA3 / ATCC 53907)
627
0
71634
TrEMBL
-
A0A5J4SSQ3_9ZZZZ
587
0
64991
TrEMBL
other Location (Reliability: 3)
A0A6M3ZH01_BACSU
Bacillus subtilis (strain 168)
632
0
71224
TrEMBL
-
A0A5J4RH61_9ZZZZ
579
2
63869
TrEMBL
other Location (Reliability: 4)
A0A075R5B1_BRELA
630
0
70948
TrEMBL
-
A0A5C6BXK8_9BACT
667
0
71938
TrEMBL
-
A0A1V6CXA5_9BACT
604
0
66827
TrEMBL
-
A0A840QP28_9BACI
605
0
69374
TrEMBL
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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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
Priestia megaterium
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 (Q796C3), Bacillus subtilis 168 (Q796C3)
brenda
Okamoto, W.; Sato, T.
Enzymatic syntheses of unnatural head-to-tail pentacyclic triterpenes by tetraprenyl-beta-curcumene cyclase
Tetrahedron Lett.
54
6747-6750
2013
Priestia megaterium, Bacillus subtilis
-
brenda
EXTERNAL LINKS (specific for EC-Number 4.2.1.137)
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Release 2023.1 (January 2023)
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