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Literature summary extracted from

  • Williams, D.R.; Trudgill, P.W.; Taylor, D.G.
    Metabolism of 1,8-cineole by a Rhodococcus species: Ring cleavage reactions (1989), J. Gen. Microbiol., 135, 1957-1967.
No PubMed abstract available

General Stability

EC Number General Stability Organism
1.14.13.51 5-10 vol% ethanol stabilizes the crude cell extract Rhodococcus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ Rhodococcus sp. involved in 1,8-cineole metabolism 6-oxocineole + NAD(P)H
-
 r
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ Rhodococcus sp. C1 involved in 1,8-cineole metabolism 6-oxocineole + NAD(P)H
-
 r
1.14.13.51 6-oxocineole + NADPH + O2 Rhodococcus grown on 1,8-cineole or succinate as carbon source 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?
1.14.13.51 6-oxocineole + NADPH + O2 Rhodococcus C1 grown on 1,8-cineole or succinate as carbon source 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.241 Rhodococcus sp.
-
-
-
1.1.1.241 Rhodococcus sp. C1
-
-
-
1.14.13.51 Rhodococcus
-
-
-
1.14.13.51 Rhodococcus C1
-
-
-
1.14.14.108 Pseudomonas putida
-
-
-
1.14.14.108 Pseudomonas putida C1 / ATCC 17453
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.13.51 partial Rhodococcus
1.14.14.108
-
 Pseudomonas putida

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.14.108 (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O mechanism Pseudomonas putida
a

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.1.1.241 0.62
-
 6-endo-hydroxycineole Rhodococcus sp.
1.1.1.241 1.08
-
 6-oxocineole Rhodococcus sp.
1.14.13.51 0.001
-
 succinate grown cells Rhodococcus
1.14.13.51 0.3 0.4 1,8-cineole-grown cells Rhodococcus

Storage Stability

EC Number Storage Stability Organism
1.1.1.241 -20°C, after dialysis against 1 mM KH2PO4/Na2HPO4 buffer, pH 7.1 Rhodococcus sp.

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ 10% of activity with NADPH over NADH in reverse reaction Rhodococcus sp. 6-oxocineole + NAD(P)H
-
 r
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ involved in 1,8-cineole metabolism Rhodococcus sp. 6-oxocineole + NAD(P)H
-
 r
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ 10% of activity with NADPH over NADH in reverse reaction Rhodococcus sp. C1 6-oxocineole + NAD(P)H
-
 r
1.1.1.241 6-endo-hydroxycineole + NAD(P)+ involved in 1,8-cineole metabolism Rhodococcus sp. C1 6-oxocineole + NAD(P)H
-
 r
1.14.13.51 6-oxocineole + NADPH + O2
-
 Rhodococcus 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?
1.14.13.51 6-oxocineole + NADPH + O2 grown on 1,8-cineole or succinate as carbon source Rhodococcus 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?
1.14.13.51 6-oxocineole + NADPH + O2
-
 Rhodococcus C1 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?
1.14.13.51 6-oxocineole + NADPH + O2 grown on 1,8-cineole or succinate as carbon source Rhodococcus C1 1,6,6-trimethyl-2,7-dioxabicyclo-[3.2.2]nonan-3-one + NADP+ + H2O this product reacts spontaneously to 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid and subsequently lactonizes to 4,5-dihydro-5,5-dimethyl-4-(3'-oxobutyl)-furan-2(3H)-one ?
1.14.13.51 additional information no substrates: substrate analogues, i.e. (+)-camphor, (S)-(+)-carvone, cyclohexanene, 1,3-cyclohexanedione, dihydrocarvone, 2-, 3-, and 4-methylcyclohexanone, fenchone, menthone, pinan-3-one, pulegone, verbenone Rhodococcus ?
-
 ?
1.14.13.51 additional information no substrates: substrate analogues, i.e. (+)-camphor, (S)-(+)-carvone, cyclohexanene, 1,3-cyclohexanedione, dihydrocarvone, 2-, 3-, and 4-methylcyclohexanone, fenchone, menthone, pinan-3-one, pulegone, verbenone Rhodococcus C1 ?
-
 ?
1.14.14.108 (+)-bornane-2,5-dione + FMNH2 + O2 i.e. 2,5-diketocamphane Pseudomonas putida 3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O i.e. cyclopentenoic acid ?
1.14.14.108 (+)-bornane-2,5-dione + FMNH2 + O2 i.e. 2,5-diketocamphane Pseudomonas putida C1 / ATCC 17453 3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O i.e. cyclopentenoic acid ?
1.14.14.108 (+)-bornanone + FMNH2 + O2 (+)-camphor Pseudomonas putida 1,2-campholide + FMN + H2O
-
 ?
1.14.14.108 (+)-bornanone + FMNH2 + O2 (+)-camphor Pseudomonas putida C1 / ATCC 17453 1,2-campholide + FMN + H2O
-
 ?
1.14.14.108 1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2 6-oxocineole Pseudomonas putida 1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
 ?
1.14.14.108 1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2 6-oxocineole Pseudomonas putida C1 / ATCC 17453 1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
 ?
1.14.14.108 6-oxocineole + FMNH2 + O2
-
 Pseudomonas putida 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
 ?
1.14.14.108 6-oxocineole + FMNH2 + O2
-
 Pseudomonas putida C1 / ATCC 17453 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
 ?
1.14.14.108 additional information rubredoxin not mentioned Pseudomonas putida ?
-
 ?
1.14.14.108 additional information rubredoxin not mentioned Pseudomonas putida C1 / ATCC 17453 ?
-
 ?

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.241 7.5
-
 NADH oxidation Rhodococcus sp.
1.1.1.241 10.5
-
 NAD+ reduction Rhodococcus sp.
1.14.13.51 9
-
-
 Rhodococcus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.241 NAD+ NADH in reverse reaction Rhodococcus sp.
1.1.1.241 NADP+ NADPH in reverse reaction, 10% of activity over NADH Rhodococcus sp.
1.14.13.51 NADP+
-
 Rhodococcus
1.14.13.51 NADPH
-
 Rhodococcus
1.14.14.108 FMN
-
 Pseudomonas putida