KEGG   ENZYME: 3.7.1.18Help
Entry
EC 3.7.1.18                 Enzyme                                 

Name
6-oxocamphor hydrolase;
OCH;
camK (gene name)
Class
Hydrolases;
Acting on carbon-carbon bonds;
In ketonic substances
BRITE hierarchy
Sysname
bornane-2,6-dione hydrolase
Reaction(IUBMB)
bornane-2,6-dione + H2O = [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate [RN:R10051]
Reaction(KEGG)
Substrate
bornane-2,6-dione [CPD:C20320];
H2O [CPD:C00001]
Product
[(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate [CPD:C20324]
Comment
Isolated from Rhodococcus sp. The bornane ring system is cleaved by a retro-Claisen reaction to give the enol of alpha-campholonate. When separate from the enzyme the enol is tautomerised to the keto form as a 6:1 mixture of [(1S,3R)-2,2,3-trimethyl-4-oxocyclopentyl]acetate and [(1S,3S)-2,2,3-trimethyl-4-oxocyclopentyl]acetate.
History
EC 3.7.1.18 created 2012
Orthology
K20765  6-oxocamphor hydrolase
Reference
1  [PMID:11278926]
  Authors
Grogan G, Roberts GA, Bougioukou D, Turner NJ, Flitsch SL
  Title
The desymmetrization of bicyclic beta -diketones by an enzymatic retro-Claisen reaction. A new reaction of the crotonase superfamily.
  Journal
J Biol Chem 276:12565-72 (2001)
DOI:10.1074/jbc.M011538200
  Sequence
Reference
2  [PMID:12421807]
  Authors
Whittingham JL, Turkenburg JP, Verma CS, Walsh MA, Grogan G
  Title
The 2-A crystal structure of 6-oxo camphor hydrolase. New structural diversity in the crotonase superfamily.
  Journal
J Biol Chem 278:1744-50 (2003)
DOI:10.1074/jbc.M211188200
  Sequence
Reference
3  [PMID:15138275]
  Authors
Leonard PM, Grogan G
  Title
Structure of 6-oxo camphor hydrolase H122A mutant bound to its natural product, (2S,4S)-alpha-campholinic acid: mutant structure suggests an atypical mode of transition state binding for a crotonase homolog.
  Journal
J Biol Chem 279:31312-7 (2004)
DOI:10.1074/jbc.M403514200
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 3.7.1.18
IUBMB Enzyme Nomenclature: 3.7.1.18
ExPASy - ENZYME nomenclature database: 3.7.1.18
BRENDA, the Enzyme Database: 3.7.1.18

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