6-oxocamphor hydrolase;
OCH;
camK (gene name)

Hydrolases;
Acting on carbon-carbon bonds;
In ketonic substances

bornane-2,6-dione hydrolase

bornane-2,6-dione + H2O = [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate [RN:R10051]

R10051

bornane-2,6-dione [CPD:C20320];
H2O [CPD:C00001]

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.

1  [PMID:11278926]

Grogan G, Roberts GA, Bougioukou D, Turner NJ, Flitsch SL

The desymmetrization of bicyclic beta -diketones by an enzymatic retro-Claisen reaction. A new reaction of the crotonase superfamily.

J. Biol. Chem. 276 (2001) 12565-72.

2  [PMID:12421807]

Whittingham JL, Turkenburg JP, Verma CS, Walsh MA, Grogan G

The 2-A crystal structure of 6-oxo camphor hydrolase. New structural diversity in the crotonase superfamily.

J. Biol. Chem. 278 (2003) 1744-50.

3  [PMID:15138275]

Leonard PM, Grogan G

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.

J. Biol. Chem. 279 (2004) 31312-7.