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Information on EC 4.1.99.16 - geosmin synthase
for references in articles please use BRENDA:EC4.1.99.16
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EC Tree 4 Lyases
4.1 Carbon-carbon lyases
4.1.99 Other carbon-carbon lyases
4.1.99.16 geosmin synthase
IUBMB Comments
Requires Mg2+. Geosmin is the cause of the characteristic smell of moist soil. It is a bifunctional enzyme. The N-terminal part of the enzyme is EC 4.2.3.22, germacradienol synthase, and forms germacradienol from FPP. The C-terminal part of the enzyme catalyses the conversion of germacradienol to geosmin via (1S,4aS,8aS)-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 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
- coelicolor
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off-flavors
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bloom
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freshwater
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amplicon
- circinalis
- 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
showSynonyms
geosmin synthase, sce1440, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Cyc2
geo
GES1
sce1440
ScGS
spterp13
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(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
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
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O = (-)-geosmin + acetone
the active site in the N-terminal domain of enzyme ScGS catalyzes the ionization-dependent cyclization of FPP to form diphosphate and two cyclic products: germacradienol (major product, 85%) and germacrene D (minor product, 15%). After dissociation from the N-terminal domain, germacradienol is rebound to the active site of the C-terminal domain where it is converted to geosmin in a protonation-dependent cyclization reaction accompanied by the elimination of acetone through a retro-Prins reaction. The tandem cyclization-fragmentation reactions catalyzed by ScGS require two distinct active sites, a unique alphaalpha domain architecture is predicted for ScGS based on primary structure analysis
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O = (-)-geosmin + acetone
the active site in the N-terminal domain of enzyme ScGS catalyzes the ionization-dependent cyclization of FPP to form diphosphate and two cyclic products: germacradienol (major product, 85%) and germacrene D (minor product, 15%). After dissociation from the N-terminal domain, germacradienol is rebound to the active site of the C-terminal domain where it is converted to geosmin in a protonation-dependent cyclization reaction accompanied by the elimination of acetone through a retro-Prins reaction. The tandem cyclization-fragmentation reactions catalyzed by ScGS require two distinct active sites, a unique alphaalpha domain architecture is predicted for ScGS based on primary structure analysis
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
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PATHWAY SOURCE
PATHWAYS
MetaCyc
geosmin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
germacradienol geosmin-lyase (acetone forming)
Requires Mg2+. Geosmin is the cause of the characteristic smell of moist soil. It is a bifunctional enzyme. The N-terminal part of the enzyme is EC 4.2.3.22, germacradienol synthase, and forms germacradienol from FPP. The C-terminal part of the enzyme catalyses the conversion of germacradienol to geosmin via (1S,4aS,8aS)-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene.
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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
(2E,6E)-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-diene-11-ol + (7S)-germacrene D + geosmin + ?
Substrates: overall reaction of germacradienol/geosmin synthase
Products: 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
Products: 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
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: catalysed by the C-terminal domain of the bifunctional enzyme
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Tricholoma vaccinum GK6514
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Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate
1(10)E,5E-germacradien-11-ol + diphosphate
-
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate
1(10)E,5E-germacradien-11-ol + diphosphate
-
Substrates: -
Products: -
Products: -
?
additional information
?
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Substrates: the geosmin synthase sce1440 from Sorangium cellulosum strain Soce56 is very substrate-specific
Products: -
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?
additional information
?
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Substrates: the geosmin synthase sce1440 from Sorangium cellulosum strain Soce56 is very substrate-specific
Products: -
Products: -
?
additional information
?
-
Substrates: nerolidyl diphosphate is excluded as an intermediate in the enzymatic formation of germacradienol, germacrene D, and geosmin
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
?
additional information
?
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-
Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
?
additional information
?
-
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
Substrates: 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
Products: -
Products: -
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
Tricholoma vaccinum GK6514
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O
(-)-geosmin + acetone
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
?
additional information
?
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Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
?
additional information
?
-
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
Substrates: geosmin synthase is a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Products: -
Products: -
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
additional information
Mg2+
each enzyme domain requires Mg2+ for catalysis, binding structure analysis at the N-terminal domain, overview
Mn2+
-
the enzyme has a strict dependency on Mg2+ that can only be substituted with Mn2+, resulting in a relative activity of 17% in comparison to Mg2+
additional information
-
no activity with Ca2+, Fe2+, Ni2+, Zn2+, and Cu2+
additional information
absolute requirement for a divalent cation. No activity with Ni2+ or Ca2+
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
i.e. ANA318, isolated at the Australian Water Quality Centre in 1995 from a sample sourced from Pejar Dam in Goulburn, NSW, Australia, during a taste and odor episode
-
-
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i.e. ANA318, isolated at the Australian Water Quality Centre in 1995 from a sample sourced from Pejar Dam in Goulburn, NSW, Australia, during a taste and odor episode
-
-
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C-terminal domain; germacradienol/germacrene D synthase
UniProt
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
-
relative enzyme expression analysis, enzyme expression under conditions of continuous light illumination and the removal of light as a stimulus appears to be constitutive, the decrease in geosmin synthase transcription post maximum cell numbers and stationary phase suggests that a decrease in isoprenoid synthesis may occur before a decrease in the transcription of ribosomal units as the process of cell death is initiated
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additional information
-
relative enzyme expression analysis, enzyme expression under conditions of continuous light illumination and the removal of light as a stimulus appears to be constitutive, the decrease in geosmin synthase transcription post maximum cell numbers and stationary phase suggests that a decrease in isoprenoid synthesis may occur before a decrease in the transcription of ribosomal units as the process of cell death is initiated
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
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
physiological function
additional information
evolution
identification of Sesquiterpene synthase orthologues of sce1440 in the genomes of myxobacterial strains, overview
evolution
-
identification of Sesquiterpene synthase orthologues of sce1440 in the genomes of myxobacterial strains, overview
-
metabolism
the enzyme is one of only three type I terpene synthases (TSs, sce1440, sce6369, sce8552) and one type II TS (sce4636), responsible for the production of at least 17 sesquiterpenes in Sorangium cellulosum
metabolism
-
the enzyme is one of only three type I terpene synthases (TSs, sce1440, sce6369, sce8552) and one type II TS (sce4636), responsible for the production of at least 17 sesquiterpenes in Sorangium cellulosum
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physiological function
mutants with a deleted geoA are unable to produce either germacradienol or geosmin
physiological function
deletion of the doxorubicin gene cluster results in increased cell growth rate along with detectable production of geosmin. Overexpression of the spterp13 gene in the Streptomyecs peucetius doxorubicin mutant leads to 2.4fold enhanced production of geosmin
physiological function
geosmin is a powerful odorant with an extremely low human detection threshold of less than 10 parts-per-trillion, and is mainly responsible for the characteristic odor of freshly turned earth. Although geosmin contributes to the pleasant, earthy flavor of beets, it is also a commonly occurring contaminant of musty-tasting water, wine, and fish. Geosmin is not known to cause human disease, but its detection and elimination from potable water sources is a critical environmental and water quality issue
physiological function
the enzyme is responsible for geosmin biosynthesis. Geosmin is a secondary metabolite responsible for earthy odors. The occurrence of geosmin has great impact on the quality of water environment. Analysis of the geosmin production under d ifferent environments
physiological function
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
-
geosmin is a powerful odorant with an extremely low human detection threshold of less than 10 parts-per-trillion, and is mainly responsible for the characteristic odor of freshly turned earth. Although geosmin contributes to the pleasant, earthy flavor of beets, it is also a commonly occurring contaminant of musty-tasting water, wine, and fish. Geosmin is not known to cause human disease, but its detection and elimination from potable water sources is a critical environmental and water quality issue
-
physiological function
-
the enzyme is responsible for geosmin biosynthesis. Geosmin is a secondary metabolite responsible for earthy odors. The occurrence of geosmin has great impact on the quality of water environment. Analysis of the geosmin production under d ifferent environments
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additional information
-
geosmin synthesis (and geosmin synthase expression) appears to be coordinated with cell growth
additional information
neither full-length ScGS nor constructs of the C-terminal domain can be crystallized, but homology models of the C-terminal domain are constructed based on about 36% sequence identity with the N-terminal domain, analysis of the crystal structure of the N-terminal domain in unliganded or liganded form, overview. Possible alpha,alpha domain architectures as frameworks for bifunctional catalysis
additional information
-
neither full-length ScGS nor constructs of the C-terminal domain can be crystallized, but homology models of the C-terminal domain are constructed based on about 36% sequence identity with the N-terminal domain, analysis of the crystal structure of the N-terminal domain in unliganded or liganded form, overview. Possible alpha,alpha domain architectures as frameworks for bifunctional catalysis
additional information
-
geosmin synthesis (and geosmin synthase expression) appears to be coordinated with cell growth
-
additional information
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
-
neither full-length ScGS nor constructs of the C-terminal domain can be crystallized, but homology models of the C-terminal domain are constructed based on about 36% sequence identity with the N-terminal domain, analysis of the crystal structure of the N-terminal domain in unliganded or liganded form, overview. Possible alpha,alpha domain architectures as frameworks for bifunctional catalysis
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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). CYC2_STRCO
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
726
0
81474
Swiss-Prot
-
A9F845_SORC5
Sorangium cellulosum (strain So ce56)
771
0
86584
TrEMBL
other Location (Reliability: 2)
B0FLN6_STRC0
732
0
81709
TrEMBL
-
Q82L49_STRAW
Streptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NBRC 14893 / NCIMB 12804 / NRRL 8165 / MA-4680)
725
0
81686
TrEMBL
-
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
geosmin synthase has alpha-alpha domain architecture. The N-terminal domain and the C-terminal domain are separated by a 41-residue linker and share 28% and 29% amino acid sequence identity, respectively, with pentalenene synthase. Each domain contains characteristic metal ion-binding motifs of class I terpenoid cyclases. The aspartate-rich motif is found as D86DHFLE91 and D455DYYP459, and the NSE/DTE motif is found as N229DLFSYQRE237 and N598DVFSYQKE606. The C-terminal domain is also predicted to adopt an alpha fold homologous to that of the N-terminal domain based on approximately 36% amino acid sequence identity between these domains. Primary, secondary and quarternary enzyme structrue analysis, and homology modeling, overview
additional information
-
geosmin synthase has alpha-alpha domain architecture. The N-terminal domain and the C-terminal domain are separated by a 41-residue linker and share 28% and 29% amino acid sequence identity, respectively, with pentalenene synthase. Each domain contains characteristic metal ion-binding motifs of class I terpenoid cyclases. The aspartate-rich motif is found as D86DHFLE91 and D455DYYP459, and the NSE/DTE motif is found as N229DLFSYQRE237 and N598DVFSYQKE606. The C-terminal domain is also predicted to adopt an alpha fold homologous to that of the N-terminal domain based on approximately 36% amino acid sequence identity between these domains. Primary, secondary and quarternary enzyme structrue analysis, and homology modeling, overview
additional information
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
-
geosmin synthase has alpha-alpha domain architecture. The N-terminal domain and the C-terminal domain are separated by a 41-residue linker and share 28% and 29% amino acid sequence identity, respectively, with pentalenene synthase. Each domain contains characteristic metal ion-binding motifs of class I terpenoid cyclases. The aspartate-rich motif is found as D86DHFLE91 and D455DYYP459, and the NSE/DTE motif is found as N229DLFSYQRE237 and N598DVFSYQKE606. The C-terminal domain is also predicted to adopt an alpha fold homologous to that of the N-terminal domain based on approximately 36% amino acid sequence identity between these domains. Primary, secondary and quarternary enzyme structrue analysis, and homology modeling, overview
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant N-terminal domain of ScGS, unliganded and in complex with 3 Mg2+ ions and alendronate, mixing of 600 nl of 7 mg/ml protein in 25 mM Tris, pH 8.2, 5 mM MgCl2, 10 mM BME, and 1.5 mM sodium alendronate, with 600 nl of precipitant solution containing 0.2 M sodium acetate trihydrate, pH 7.0, and 20% w/v PEG 3350, and equilibration against 0.1 ml of reservoir solution at room temperature, X-ray diffraction structure determination and analysis at 2.4 A resolution. Neither full-length ScGS nor constructs of the C-terminal domain can be crystallized, but homology models of the C-terminal domain are constructed based on about 36% sequence identity with the N-terminal domain
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His6-tagged full-length enzyme from Escherichia coli strain BL21(DE3)pLysS by nickel affinity chromatography, recombinant N-terminal domain of ScGS (residues 1-366) from Escherichia coli strain BL21(DE3)pLysS by ammonium sulfate fractionation, adsorption chromatography on methyl resin, gel filtration, and ultrafiltartion
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene cyc2, recombinant expression of C-terminally His6-tagged full-length enzyme and of the N-terminal domain of ScGS (residues 1-366) in Escherichia coli strain BL21(DE3)pLysS , subcloning in Escherichia coli strain XL-1 Blue
gene geo, cloning of full-length of geosmin synthase gene from Aphanizomenon gracile strain WH-1, DNA and amino acid sequence determination and analysis, phylogenetic tree, real time PCR is applied to quantify the geosmin production in different light and temperature. Low temperature (15°C), high light intensity (0.035 mmol/s/m) and continuous light illumination are beneficial to the expression of geo. The successful amplification of geosmin synthase gene verifies that hiTAIL-PCR is an effective and simple procedure of low cost
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Cane, D.E.; He, X.; Kobayashi, S.; Omura, S.; Ikeda, H.
Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase
J. Antibiot.
59
471-479
2006
Streptomyces avermitilis (Q82L49)
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Jiang, J.; Cane, D.E.
Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin
J. Am. Chem. Soc.
130
428-429
2008
Streptomyces coelicolor (Q9X839)
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Singh, B.; Oh, T.J.; Sohng, J.K.
Exploration of geosmin synthase from Streptomyces peucetius ATCC 27952 by deletion of doxorubicin biosynthetic gene cluster
J. Ind. Microbiol. Biotechnol.
36
1257-1265
2009
Streptomyces peucetius (B0FLN6), Streptomyces peucetius, Streptomyces peucetius ATCC 27952 (B0FLN6)
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Giglio, S.; Saint, C.; Monis, P.
Expression of the geosmin synthase gene in the cyanobacterium Anabaena circinalis AWQC318
J. Phycol.
47
1338-1343
2011
Dolichospermum circinale, Dolichospermum circinale AWQC318
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Schifrin, A.; Khatri, Y.; Kirsch, P.; Thiel, V.; Schulz, S.; Bernhardt, R.
A single terpene synthase is responsible for a wide variety of sesquiterpenes in Sorangium cellulosum Soce56
Org. Biomol. Chem.
14
3385-3393
2016
Sorangium cellulosum (A9F845), Sorangium cellulosum Soce56 (A9F845)
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Harris, G.G.; Lombardi, P.M.; Pemberton, T.A.; Matsui, T.; Weiss, T.M.; Cole, K.E.; Koeksal, M.; Murphy, F.V.; Vedula, L.S.; Chou, W.K.; Cane, D.E.; Christianson, D.W.
Structural studies of geosmin synthase, a bifunctional sesquiterpene synthase with alpha-alpha domain architecture that catalyzes a unique cyclization fragmentation reaction sequence
Biochemistry
54
7142-7155
2015
Streptomyces coelicolor (Q9X839), Streptomyces coelicolor, Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145 (Q9X839)
brenda
Zhou, W.; Li, G.; Gao, X.; Dai, L.; Guo, L.; Wang, S.
Cloning and expression analysis of geosmin synthase gene from Aphanizomenon gracile
Chin. J. Appl. Environ. Biol.
21
824-829
2015
Aphanizomenon gracile (A0A0D5W9R1), Aphanizomenon gracile WH-1 (A0A0D5W9R1)
-
brenda
Xu, H.; Dickschat, J.S.
A detailed view on geosmin biosynthesis
ChemBioChem
2023
e202300101
2023
Allokutzneria albata, Allokutzneria albata NRRL B-24461
brenda
Abdulsalam, O.; Ueberschaar, N.; Krause, K.; Kothe, E.
Geosmin synthase ges1 knock-down by siRNA in the dikaryotic fungus Tricholoma vaccinum
J. Basic Microbiol.
62
109-115
2022
Tricholoma vaccinum, Tricholoma vaccinum GK6514
brenda
Wang, Z.; Song, G.; Li, Y.; Yu, G.; Hou, X.; Gan, Z.; Li, R.
The diversity, origin, and evolutionary analysis of geosmin synthase gene in cyanobacteria
Sci. Total Environ.
689
789-796
2019
Anabaena minutissima, Anabaena minutissima FACHB 250, Aphanizomenon gracile, Aphanizomenon gracile CHAB 2417, Aphanizomenon sp. CHAB1684, Calothrix sp. CHAB2384, Calothrix sp. NIES-2100, Calothrix sp. PCC 7507, Cylindrospermum sp. CHAB2115, Cylindrospermum stagnale, Cylindrospermum stagnale PCC 7417, Dolichospermum circinale, Dolichospermum circinale CHAB 3585, Dolichospermum planctonicum, Dolichospermum planctonicum SDZ-1, Dolichospermum ucrainicum, Dolichospermum ucrainicum CHAB 1434, Kamptonema sp. PCC 6506, Lyngbya kuetzingii, Lyngbya kuetzingii FACHB 388, Nodosilinea bijugata, Nodularia sp. Su-A, Nostoc commune, Nostoc commune FACHB 261, Nostoc flagelliforme, Nostoc flagelliforme CHAB 2816, Nostoc linckia, Nostoc linckia NIES-25, Nostoc punctiforme, Nostoc sp. NIES-2111, Phormidium sp. D6, Scytonema sp. CHAB3651, Tychonema bourrellyi, Tychonema bourrellyi CHAB 663
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EXTERNAL LINKS (specific for EC-Number 4.1.99.16)
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