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
Genes
GQU: 
KOR: 
BGJ: 
PAO: 
TCI: 
HAK: 
GSN: 
SDF: 
BCM: 
BGP: 
BUQ: 
BPLA: 
PSPW: 
RDP: 
MES: 
BRA: 
AOL: 
XAU: 
MOR: 
MAQU: 
MEY: 
MMED: 
Mame_04324(paaF_3)
MALG: 
NPN: 
SMAZ: 
SGI: 
SWI: 
SPHJ: 
SCH: 
SYB: 
SPMI: 
SPHT: 
SPHG: 
ATI: 
NAO: 
PPOL: 
PTA: 
PGM: 
PAEN: 
PAEQ: 
PAEH: 
PRI: 
PPEO: 
CBZ: 
CBEI: 
CLS: 
GFE: 
CCT: 
FPLA: 
PFT: 
MSM: 
MSG: 
MSB: 
MSN: 
MSH: 
MRH: 
MGO: 
SRC: 
SAUO: 
SRO: 
FRE: 
FRI: 
FSY: 
PSEQ: 
PECQ: 
GVI: 
ANA: 
NOS: 
AVA: 
 » show all
Taxonomy
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 (2001) 12565-72.
  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 (2003) 1744-50.
  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 (2004) 31312-7.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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