3.7.1.11: cyclohexane-1,2-dione hydrolase
This is an abbreviated version!
For detailed information about cyclohexane-1,2-dione hydrolase, go to the full flat file.
Reaction
Synonyms
Cdh, ThDP-dependent cyclohexane-1,2-dione hydrolase, thiamine diphosphate dependent cyclohexane-1,2-dione hydrolase
ECTree
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Reaction
Reaction on EC 3.7.1.11 - cyclohexane-1,2-dione hydrolase
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cyclohexane-1,2-dione + H2O = 6-oxohexanoate
catalytic reaction mechanism, overview
cyclohexane-1,2-dione + H2O = 6-oxohexanoate
catalytic reaction mechanism, overview
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cyclohexane-1,2-dione + H2O = 6-oxohexanoate
reaction starts with the monohydrated ketone of cyclohexane-1,2-dione and the thiamine diphosphate-ylide which undergoes a nucleophilic attack on the carbonyl group of cyclohexane-1,2-dione. The subsequent cleavage of the CC bond yields an alpha-carbanion, which is in equilibrium with its corresponding enamine. In the following step, the carbonic acid protonates the alpha-carbanion yielding 6-hydroxyhexanoate-thiamine diphosphate. Finally, the product 6-oxohexanoate is released
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cyclohexane-1,2-dione + H2O = 6-oxohexanoate
the C-C bond cleavage is assumed to be initiated by the attack of the ThDP ylide on the C=O bond of the monohydrate 6 of 1,2-diketone 4 to form the ThDP adduct, a tetrahedral intermediate which breaks down to a carboxylic acid
cyclohexane-1,2-dione + H2O = 6-oxohexanoate
the thiamine diphosphate-dependent enzyme involves a C-C bond ring cleavage of alicyclic compound, catalytic mechanism analysis by quantum mechanics/molecular mechanics, molecular docking simulations and modeling
cyclohexane-1,2-dione + H2O = 6-oxohexanoate
reaction starts with the monohydrated ketone of cyclohexane-1,2-dione and the thiamine diphosphate-ylide which undergoes a nucleophilic attack on the carbonyl group of cyclohexane-1,2-dione. The subsequent cleavage of the CC bond yields an alpha-carbanion, which is in equilibrium with its corresponding enamine. In the following step, the carbonic acid protonates the alpha-carbanion yielding 6-hydroxyhexanoate-thiamine diphosphate. Finally, the product 6-oxohexanoate is released
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cyclohexane-1,2-dione + H2O = 6-oxohexanoate
catalytic reaction mechanism, overview
-
-
cyclohexane-1,2-dione + H2O = 6-oxohexanoate
the C-C bond cleavage is assumed to be initiated by the attack of the ThDP ylide on the C=O bond of the monohydrate 6 of 1,2-diketone 4 to form the ThDP adduct, a tetrahedral intermediate which breaks down to a carboxylic acid
-
-
cyclohexane-1,2-dione + H2O = 6-oxohexanoate
the thiamine diphosphate-dependent enzyme involves a C-C bond ring cleavage of alicyclic compound, catalytic mechanism analysis by quantum mechanics/molecular mechanics, molecular docking simulations and modeling
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