Parent Class:

EC-Numbers → 3 -- Hydrolases → 3.7 -- Acting on carbon-carbon bonds → 3.7.1 -- In ketonic substances

Synonyms: OCH, camK (gene name)

Systematic Name: bornane-2,6-dione hydrolase

Unification Links: BRENDA:3.7.1.18, ENZYME:3.7.1.18, IUBMB-ExplorEnz:3.7.1.18

Reaction:
6-oxocamphor + H₂O → [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate + H⁺

Enzymes and Genes:
6-oxocamphor hydrolase: camK ( Rhodococcus sp. NCIMB 9784 )

Summary:
Isolated from Rhodococcus sp. NCIMB 9784. The bornane ring system is cleaved by a retro-Claisen reaction to give the enol of α-campholonate. When separate from the enzyme the enol from 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.

Citations: [Grogan01, Whittingham03, Leonard04]

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References

Grogan01: Grogan G, Roberts GA, Bougioukou D, Turner NJ, Flitsch SL (2001). "The desymmetrization of bicyclic beta -diketones by an enzymatic retro-Claisen reaction. A new reaction of the crotonase superfamily." J Biol Chem 276(16);12565-72. PMID: 11278926

Leonard04: Leonard PM, Grogan G (2004). "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(30);31312-7. PMID: 15138275

Whittingham03: Whittingham JL, Turkenburg JP, Verma CS, Walsh MA, Grogan G (2003). "The 2-A crystal structure of 6-oxo camphor hydrolase. New structural diversity in the crotonase superfamily." J Biol Chem 278(3);1744-50. PMID: 12421807

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 46(D1):D633-D639 2018
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