4.1.99.16: geosmin synthase
This is an abbreviated version!
For detailed information about geosmin synthase, go to the full flat file.
Word Map on EC 4.1.99.16
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4.1.99.16
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odor
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geosmin-producing
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taste
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anabaena
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cyanobacterial
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isoprenoid
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sesquiterpene
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coelicolor
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off-flavors
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bloom
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freshwater
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amplicon
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circinalis
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2-methylisoborneol
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terpenoid
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terpene
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trouble
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dolichospermum
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on-site
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aquaculture
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farnesyl
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bornet
- 4.1.99.16
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odor
-
geosmin-producing
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taste
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anabaena
-
cyanobacterial
-
isoprenoid
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sesquiterpene
- coelicolor
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off-flavors
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bloom
-
freshwater
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amplicon
- circinalis
- 2-methylisoborneol
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terpenoid
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terpene
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trouble
-
dolichospermum
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on-site
-
aquaculture
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farnesyl
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bornet
Reaction
Synonyms
Cyc2, geo, geoA, sce1440, ScGS, spterp13
ECTree
4.1.99.16 geosmin synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.1.99.16 - geosmin synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-diene-11-ol + (7S)-germacrene D + geosmin + ?
overall reaction of germacradienol/geosmin synthase
presence of Mg2+, synthesis of 66% (4S,7R)-germacra-1(10)E,5E-diene-11-ol, 24% (7S)-germacrene D, 8% geosmin, and 2% of a hydrocarbon, tentatively assigned the structure of octalin
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
catalysed by the C-terminal domain of the bifunctional enzyme
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?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
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?
additional information
?
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the geosmin synthase sce1440 from Sorangium cellulosum strain Soce56 is very substrate-specific
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?
additional information
?
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the geosmin synthase sce1440 from Sorangium cellulosum strain Soce56 is very substrate-specific
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?
additional information
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nerolidyl diphosphate is excluded as an intermediate in the enzymatic formation of germacradienol, germacrene D, and geosmin
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?
additional information
?
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conversion of germacradienol to geosmin results in the release of the three-carbon side chain as acetone and involves a 1,2-hydride shift of the bridgehead hydrogen exclusively into ring B of geosmin
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?
additional information
?
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geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
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?
additional information
?
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geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
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?
additional information
?
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geosmin synthase from Streptomyces coelicolor (ScGS) catalyzes an unusual, metal-dependent terpenoid cyclization and fragmentation reaction sequence. Two distinct active sites are required for catalysis: the N-terminal domain catalyzes the ionization and cyclization of farnesyl diphosphate to form germacradienol and inorganic pyrophosphate (PPi), and the C-terminal domain catalyzes the protonation, cyclization, and fragmentation of germacradienol to form geosmin and acetone through a retro-Prins reaction. The enzyme has an alpha,alpha domain architecture, each domain contains the metal-binding motifs typical of a class I terpenoid cyclase, and each domain requires Mg2+ for catalysis. There is no direct channel for transfer of the intermediate from the active site of the N-terminal domain to that of the C-terminal domain. It is a diiffusive transfer of the germacradienol intermediate
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?
additional information
?
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geosmin synthase from Streptomyces coelicolor (ScGS) catalyzes an unusual, metal-dependent terpenoid cyclization and fragmentation reaction sequence. Two distinct active sites are required for catalysis: the N-terminal domain catalyzes the ionization and cyclization of farnesyl diphosphate to form germacradienol and inorganic pyrophosphate (PPi), and the C-terminal domain catalyzes the protonation, cyclization, and fragmentation of germacradienol to form geosmin and acetone through a retro-Prins reaction. The enzyme has an alpha,alpha domain architecture, each domain contains the metal-binding motifs typical of a class I terpenoid cyclase, and each domain requires Mg2+ for catalysis. There is no direct channel for transfer of the intermediate from the active site of the N-terminal domain to that of the C-terminal domain. It is a diiffusive transfer of the germacradienol intermediate
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?
additional information
?
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Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
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?
additional information
?
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Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
geosmin synthase from Streptomyces coelicolor (ScGS) catalyzes an unusual, metal-dependent terpenoid cyclization and fragmentation reaction sequence. Two distinct active sites are required for catalysis: the N-terminal domain catalyzes the ionization and cyclization of farnesyl diphosphate to form germacradienol and inorganic pyrophosphate (PPi), and the C-terminal domain catalyzes the protonation, cyclization, and fragmentation of germacradienol to form geosmin and acetone through a retro-Prins reaction. The enzyme has an alpha,alpha domain architecture, each domain contains the metal-binding motifs typical of a class I terpenoid cyclase, and each domain requires Mg2+ for catalysis. There is no direct channel for transfer of the intermediate from the active site of the N-terminal domain to that of the C-terminal domain. It is a diiffusive transfer of the germacradienol intermediate
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?
