3.7.1.18: 6-oxocamphor hydrolase
This is an abbreviated version!
For detailed information about 6-oxocamphor hydrolase, go to the full flat file.
Word Map on EC 3.7.1.18
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3.7.1.18
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crotonase
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desymmetrization
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beta-diketones
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bicyclic
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diketone
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rhodococcus
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ncimb
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prochiral
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enol
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hexamer
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anabaena
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trimer
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dyad
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carbon-carbon
- 3.7.1.18
- crotonase
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desymmetrization
- beta-diketones
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bicyclic
- diketone
- rhodococcus
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ncimb
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prochiral
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enol
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hexamer
- anabaena
- trimer
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dyad
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carbon-carbon
Reaction
Synonyms
6-oxo camphor hydrolase, CaMK, OCH, retro-Claisenase
ECTree
3.7.1.18 6-oxocamphor hydrolaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 3.7.1.18 - 6-oxocamphor hydrolase
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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
7,7-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-3,3-dimethyl-5-oxocyclohexyl]acetic acid
8,8-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-2,2-dimethyl-5-oxocyclohexyl]acetic acid
1-allylbicyclo-[4.3.0]nonane-2,9-dione + H2O
?
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i.e. 7a-allylhexahydroindene-1,7-dione
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?
1-allylbicyclo-[4.3.0]nonane-2,9-dione + H2O
?
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i.e. 7a-allylhexahydroindene-1,7-dione
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?
1-methylbicyclo-[4.3.0]nonane-2,9-dione + H2O
?
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OCH catalyses the resolution of 1-methylbicyclo-[4.3.0]nonane-2,9-dione, i.e. 7a-methylhexahydroindene-1,7-dione
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?
1-methylbicyclo-[4.3.0]nonane-2,9-dione + H2O
?
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OCH catalyses the resolution of 1-methylbicyclo-[4.3.0]nonane-2,9-dione, i.e. 7a-methylhexahydroindene-1,7-dione
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?
1-methylbicyclo[5.3.0]decane-2,10-dione + H2O
?
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i.e. 8a-methyloctahydroazulene-1,8-dione
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?
1-methylbicyclo[5.3.0]decane-2,10-dione + H2O
?
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i.e. 8a-methyloctahydroazulene-1,8-dione
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-
?
6-oxocamphor + H2O
(2R,4S)-alpha-campholinic acid
the 6-oxocamphor hydrolase catalyzes the desymmetrization of 6-oxocamphor to yield (2R,4S)-alpha-campholinic acid, putative asymmetric hydrolysis mechanism for 6-oxocamphor hydrolase based on sequence homology and the known mechanism of the crotonase enzymes, overview
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-
?
6-oxocamphor + H2O
(2R,4S)-alpha-campholinic acid
the 6-oxocamphor hydrolase catalyzes the desymmetrization of 6-oxocamphor to yield (2R,4S)-alpha-campholinic acid, putative asymmetric hydrolysis mechanism for 6-oxocamphor hydrolase based on sequence homology and the known mechanism of the crotonase enzymes, overview
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-
?
7,7-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-3,3-dimethyl-5-oxocyclohexyl]acetic acid
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?
7,7-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-3,3-dimethyl-5-oxocyclohexyl]acetic acid
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?
8,8-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-2,2-dimethyl-5-oxocyclohexyl]acetic acid
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?
8,8-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
[(1S)-2,2-dimethyl-5-oxocyclohexyl]acetic acid
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-
-
?
bicyclo[2.2.2]octan-2,6-dione + H2O
[(1S)-3-oxocyclohexyl]acetic acid
the enzyme 6-oxocamphor hydrolase catalyses the hydrolytic retro-Claisen condensation of non-enolisable, symmetrical beta-diketones leading to optically pure keto acid [(1S)-3-oxocyclohexyl]acetic acid, it catalyses the hydrolysis of bicyclo[2.2.2]octan-2,6-dione to [(1S)-3-oxocyclohexyl]acetic acid with full conversion and perfect stereoselectivity (ee >99%) within three hours
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-
?
bicyclo[2.2.2]octan-2,6-dione + H2O
[(1S)-3-oxocyclohexyl]acetic acid
the enzyme 6-oxocamphor hydrolase catalyses the hydrolytic retro-Claisen condensation of non-enolisable, symmetrical beta-diketones leading to optically pure keto acid [(1S)-3-oxocyclohexyl]acetic acid, it catalyses the hydrolysis of bicyclo[2.2.2]octan-2,6-dione to [(1S)-3-oxocyclohexyl]acetic acid with full conversion and perfect stereoselectivity (ee >99%) within three hours
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?
bornane-2,6-dione + H2O
[(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
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?
bornane-2,6-dione + H2O
[(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
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?
additional information
?
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6-oxo camphor hydrolase catalyzes carbon-carbon bond cleavage in bicyclic beta-diketones via a retro-Claisen reaction
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?
additional information
?
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modeling of the substrate, 6-oxo camphor, and a proposed enolate intermediate in the putative active site suggesting possible mechanistic roles for Glu244, Asp154, His122, His45, and His145, overview
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?
additional information
?
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the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product
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-
?
additional information
?
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substrate specificity and enantioselectivity, competence of the enzyme for kinetic resolutions of asymmetric, racemic substrates, modeling, overview. Increasing the length of the alkyl chain in the 1-position, or enlarging one ofthe rings, increases the enantioselectivity of the enzyme to 5.7 and 3.1 for the substrates 1-allylbicyclo-[4.3.0]nonane-2,9-dione (7a-allylhexahydroindene-1,7-dione) and 1-methylbicyclo[5.3.0]decane-2,10-dione (8a-methyloctahydroazulene-1,8-dione), respectively. 1-Methylbicyclo[5.4.0]undecane-2,10-dione, i.e. 9a-methyloctahydrobenzocycloheptene-1,9-dione, is not a substrate for OCH
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?
additional information
?
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prochiral bicyclic diketones are transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres are set up by the C-C hydrolase 6-oxocamphor hydrolase in the first step and by an omega-transaminase in the last step. The esterification of the intermediate keto acid is catalysed by a lipase in the second step if possible, method overview. The cis- as well as the trans-diastereomers can be obtained in optically pure forms
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?
additional information
?
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the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product
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-
?
additional information
?
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substrate specificity and enantioselectivity, competence of the enzyme for kinetic resolutions of asymmetric, racemic substrates, modeling, overview. Increasing the length of the alkyl chain in the 1-position, or enlarging one ofthe rings, increases the enantioselectivity of the enzyme to 5.7 and 3.1 for the substrates 1-allylbicyclo-[4.3.0]nonane-2,9-dione (7a-allylhexahydroindene-1,7-dione) and 1-methylbicyclo[5.3.0]decane-2,10-dione (8a-methyloctahydroazulene-1,8-dione), respectively. 1-Methylbicyclo[5.4.0]undecane-2,10-dione, i.e. 9a-methyloctahydrobenzocycloheptene-1,9-dione, is not a substrate for OCH
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-
?
additional information
?
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prochiral bicyclic diketones are transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres are set up by the C-C hydrolase 6-oxocamphor hydrolase in the first step and by an omega-transaminase in the last step. The esterification of the intermediate keto acid is catalysed by a lipase in the second step if possible, method overview. The cis- as well as the trans-diastereomers can be obtained in optically pure forms
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?
