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Literature summary for 3.7.1.18 extracted from

  • Hill, C.; Lee, C.; Smith, D.; Verma, C.; Grogan, G.
    On the resolution of chiral substrates by a retro-Claisenase enzyme: biotransformations of heteroannular bicyclic beta-diketones by 6-oxocamphor hydrolase (2007), Adv. Synth. Catal., 349, 1353-1360.
No PubMed abstract available
Search for more literature for 3.7.1.18

Cloned(Commentary)

Cloned (Comment) Organism
gene camK, expression in Escherichia coli strain BL21 (DE3) Rhodococcus sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Rhodococcus sp. the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product ?
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 ?
additional information Rhodococcus sp. NCIMB 9784 the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product ?
-
 ?

Organism

Organism UniProt Comment Textmining
Rhodococcus sp.
-
-
-
Rhodococcus sp. NCIMB 9784
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-
-

Reaction

Reaction Comment Organism Reaction ID
bornane-2,6-dione + H2O = [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate analysis of the molecular determinants of both mechanism and enantiotopic selectivity in reactions catalysed by OCH and reaction mechanism, putative Asp154-His145 dyad, overview Rhodococcus sp.
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1-allylbicyclo-[4.3.0]nonane-2,9-dione + H2O i.e. 7a-allylhexahydroindene-1,7-dione Rhodococcus sp. ?
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 ?
1-allylbicyclo-[4.3.0]nonane-2,9-dione + H2O i.e. 7a-allylhexahydroindene-1,7-dione Rhodococcus sp. NCIMB 9784 ?
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 ?
1-methylbicyclo-[4.3.0]nonane-2,9-dione + H2O OCH catalyses the resolution of 1-methylbicyclo-[4.3.0]nonane-2,9-dione, i.e. 7a-methylhexahydroindene-1,7-dione Rhodococcus sp. ?
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 ?
1-methylbicyclo-[4.3.0]nonane-2,9-dione + H2O OCH catalyses the resolution of 1-methylbicyclo-[4.3.0]nonane-2,9-dione, i.e. 7a-methylhexahydroindene-1,7-dione Rhodococcus sp. NCIMB 9784 ?
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 ?
1-methylbicyclo[5.3.0]decane-2,10-dione + H2O i.e. 8a-methyloctahydroazulene-1,8-dione Rhodococcus sp. ?
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 ?
1-methylbicyclo[5.3.0]decane-2,10-dione + H2O i.e. 8a-methyloctahydroazulene-1,8-dione Rhodococcus sp. NCIMB 9784 ?
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 ?
bicyclo[2.2.2]octane-2,6-dione + H2O
-
 Rhodococcus sp. ?
-
 ?
additional information the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product Rhodococcus sp. ?
-
 ?
additional information substrate specificity and enantioselectivity, competence of the enzyme for kinetic resolutions of asymmetric, racemic substrates, modeling, overview. Increasing the length of the alkyl chain in the 1-position, or enlarging one ofthe rings, increases the enantioselectivity of the enzyme to 5.7 and 3.1 for the substrates 1-allylbicyclo-[4.3.0]nonane-2,9-dione (7a-allylhexahydroindene-1,7-dione) and 1-methylbicyclo[5.3.0]decane-2,10-dione (8a-methyloctahydroazulene-1,8-dione), respectively. 1-Methylbicyclo[5.4.0]undecane-2,10-dione, i.e. 9a-methyloctahydrobenzocycloheptene-1,9-dione, is not a substrate for OCH Rhodococcus sp. ?
-
 ?
additional information the transformation catalysed by OCH in nature is the cleavage, by a retro-Claisen reaction, of the bicyclic diketone 6-oxocamphor to alpha-campholinic acid, a reaction that proceeds with high diastereoselectivity and enantioselectivity in favour of the (2R,4S)-enantiomer of the product Rhodococcus sp. NCIMB 9784 ?
-
 ?
additional information substrate specificity and enantioselectivity, competence of the enzyme for kinetic resolutions of asymmetric, racemic substrates, modeling, overview. Increasing the length of the alkyl chain in the 1-position, or enlarging one ofthe rings, increases the enantioselectivity of the enzyme to 5.7 and 3.1 for the substrates 1-allylbicyclo-[4.3.0]nonane-2,9-dione (7a-allylhexahydroindene-1,7-dione) and 1-methylbicyclo[5.3.0]decane-2,10-dione (8a-methyloctahydroazulene-1,8-dione), respectively. 1-Methylbicyclo[5.4.0]undecane-2,10-dione, i.e. 9a-methyloctahydrobenzocycloheptene-1,9-dione, is not a substrate for OCH Rhodococcus sp. NCIMB 9784 ?
-
 ?

Synonyms

Synonyms Comment Organism
OCH
-
 Rhodococcus sp.
retro-Claisenase
-
 Rhodococcus sp.

General Information

General Information Comment Organism
metabolism the 6-oxocamphor hydrolase is involved in the metabolism of (1 R)-(+)-camphor Rhodococcus sp.