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Literature summary for 3.7.1.18 extracted from

  • Siirola, E.; Mutti, F.; Grischek, B.; Hoefler, S.; Fabian, W.; Grogan, G.; Kroutil, W.
    Asymmetric synthesis of 3-substituted cyclohexylamine derivatives from prochiral diketones via three biocatalytic steps (2013), Adv. Synth. Catal., 355, 1703-1708.
No PubMed abstract available
Search for more literature for 3.7.1.18

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression in Escherichia coli Rhodococcus sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
bornane-2,6-dione + H2O Rhodococcus sp.
-
 [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
-
 ?
bornane-2,6-dione + H2O Rhodococcus sp. NCIMB 9784
-
 [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
-
 ?

Organism

Organism UniProt Comment Textmining
Rhodococcus sp. Q93TU6
-
-
Rhodococcus sp. NCIMB 9784 Q93TU6
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme from Escherichia coli Rhodococcus sp.

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7,7-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
-
 Rhodococcus sp. [(1S)-3,3-dimethyl-5-oxocyclohexyl]acetic acid
-
 ?
7,7-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
-
 Rhodococcus sp. NCIMB 9784 [(1S)-3,3-dimethyl-5-oxocyclohexyl]acetic acid
-
 ?
8,8-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
-
 Rhodococcus sp. [(1S)-2,2-dimethyl-5-oxocyclohexyl]acetic acid
-
 ?
8,8-dimethylbicyclo[2.2.2]octane-2,6-dione + H2O
-
 Rhodococcus sp. NCIMB 9784 [(1S)-2,2-dimethyl-5-oxocyclohexyl]acetic acid
-
 ?
bicyclo[2.2.2]octan-2,6-dione + H2O the enzyme 6-oxocamphor hydrolase catalyses the hydrolytic retro-Claisen condensation of non-enolisable, symmetrical beta-diketones leading to optically pure keto acid [(1S)-3-oxocyclohexyl]acetic acid, it catalyses the hydrolysis of bicyclo[2.2.2]octan-2,6-dione to [(1S)-3-oxocyclohexyl]acetic acid with full conversion and perfect stereoselectivity (ee >99%) within three hours Rhodococcus sp. [(1S)-3-oxocyclohexyl]acetic acid
-
 ?
bicyclo[2.2.2]octan-2,6-dione + H2O the enzyme 6-oxocamphor hydrolase catalyses the hydrolytic retro-Claisen condensation of non-enolisable, symmetrical beta-diketones leading to optically pure keto acid [(1S)-3-oxocyclohexyl]acetic acid, it catalyses the hydrolysis of bicyclo[2.2.2]octan-2,6-dione to [(1S)-3-oxocyclohexyl]acetic acid with full conversion and perfect stereoselectivity (ee >99%) within three hours Rhodococcus sp. NCIMB 9784 [(1S)-3-oxocyclohexyl]acetic acid
-
 ?
bornane-2,6-dione + H2O
-
 Rhodococcus sp. [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
-
 ?
bornane-2,6-dione + H2O
-
 Rhodococcus sp. NCIMB 9784 [(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetate
-
 ?
additional information prochiral bicyclic diketones are transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres are set up by the C-C hydrolase 6-oxocamphor hydrolase in the first step and by an omega-transaminase in the last step. The esterification of the intermediate keto acid is catalysed by a lipase in the second step if possible, method overview. The cis- as well as the trans-diastereomers can be obtained in optically pure forms Rhodococcus sp. ?
-
 ?
additional information prochiral bicyclic diketones are transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres are set up by the C-C hydrolase 6-oxocamphor hydrolase in the first step and by an omega-transaminase in the last step. The esterification of the intermediate keto acid is catalysed by a lipase in the second step if possible, method overview. The cis- as well as the trans-diastereomers can be obtained in optically pure forms Rhodococcus sp. NCIMB 9784 ?
-
 ?

Synonyms

Synonyms Comment Organism
OCH
-
 Rhodococcus sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at Rhodococcus sp.