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Information on EC 4.2.1.137 - sporulenol synthase and Organism(s) Bacillus subtilis and UniProt Accession Q796C3

for references in articles please use BRENDA:EC4.2.1.137
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EC Tree
     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.1 Hydro-lyases
                4.2.1.137 sporulenol synthase
IUBMB Comments
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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Bacillus subtilis
UNIPROT: Q796C3
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The taxonomic range for the selected organisms is: Bacillus subtilis
The enzyme appears in selected viruses and cellular organisms
Synonyms
sqhC, tetraprenyl-beta-curcumene cyclase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetraprenyl-beta-curcumene cyclase
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sqhC
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tetraprenyl-beta-curcumene cyclase
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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.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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
show the reaction diagram
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the product is further converted by nonenzymatic autoxidation and thermal dehydration, overview
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?
beta-hexaprene
?
show the reaction diagram
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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
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?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
show the reaction diagram
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-
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?
additional information
?
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the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
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?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
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
show the reaction diagram
-
-
-
?
tetraprenyl-beta-curcumene + H2O
baciterpenol A
show the reaction diagram
-
-
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-
?
additional information
?
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the enzyme forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo
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?
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene sqhC
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
tetraprenyl-beta-curcumene cyclase shows no sequence homology to any of the known terpene cyclases
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
evolution
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the enzyme is a sesquarterpene cyclase
metabolism
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the enzyme is involved in biosynthetic pathway of sesquarterpenes (C35), overview
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene sqhC, expression in Escherichia coli using pColdTF
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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)
Manually annotated by BRENDA team
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
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Manually annotated by BRENDA team