BRENDA - Enzyme Database

Metabolism of 1,8-cineole by a Rhodococcus species: Ring cleavage reactions

Williams, D.R.; Trudgill, P.W.; Taylor, D.G.; J. Gen. Microbiol. 135, 1957-1967 (1989)
No PubMed abstract available

Data extracted from this reference:

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
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
Rhodococcus sp.
involved in 1,8-cineole metabolism
6-oxocineole + NAD(P)H
-
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
Rhodococcus sp. C1
involved in 1,8-cineole metabolism
6-oxocineole + NAD(P)H
-
Rhodococcus sp. C1
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
Rhodococcus
?
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
Rhodococcus C1
?
Organism
EC Number
Organism
UniProt
Commentary
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 (Commentary)
Organism
1.14.13.51
partial
Rhodococcus
1.14.14.108
-
Pseudomonas putida
Reaction
EC Number
Reaction
Commentary
Organism
Reaction ID
1.14.14.108
(+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O
mechanism
Pseudomonas putida
Specific Activity [micromol/min/mg]
EC Number
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
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
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
10% of activity with NADPH over NADH in reverse reaction
286367
Rhodococcus sp.
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
involved in 1,8-cineole metabolism
286367
Rhodococcus sp.
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
10% of activity with NADPH over NADH in reverse reaction
286367
Rhodococcus sp. C1
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp. C1
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
involved in 1,8-cineole metabolism
286367
Rhodococcus sp. C1
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp. C1
r
1.14.13.51
6-oxocineole + NADPH + O2
-
286367
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
286367
Rhodococcus
?
1.14.13.51
6-oxocineole + NADPH + O2
grown on 1,8-cineole or succinate as carbon source
286367
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
286367
Rhodococcus
?
1.14.13.51
6-oxocineole + NADPH + O2
-
286367
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
286367
Rhodococcus C1
?
1.14.13.51
6-oxocineole + NADPH + O2
grown on 1,8-cineole or succinate as carbon source
286367
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
286367
Rhodococcus C1
?
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
286367
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
286367
Rhodococcus C1
?
-
-
-
?
1.14.14.108
(+)-bornane-2,5-dione + FMNH2 + O2
i.e. 2,5-diketocamphane
286367
Pseudomonas putida
3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O
i.e. cyclopentenoic acid
286367
Pseudomonas putida
?
1.14.14.108
(+)-bornane-2,5-dione + FMNH2 + O2
i.e. 2,5-diketocamphane
286367
Pseudomonas putida C1 / ATCC 17453
3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O
i.e. cyclopentenoic acid
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
(+)-bornanone + FMNH2 + O2
(+)-camphor
286367
Pseudomonas putida
1,2-campholide + FMN + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
(+)-bornanone + FMNH2 + O2
(+)-camphor
286367
Pseudomonas putida C1 / ATCC 17453
1,2-campholide + FMN + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2
6-oxocineole
286367
Pseudomonas putida
1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2
6-oxocineole
286367
Pseudomonas putida C1 / ATCC 17453
1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
6-oxocineole + FMNH2 + O2
-
286367
Pseudomonas putida
3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
6-oxocineole + FMNH2 + O2
-
286367
Pseudomonas putida C1 / ATCC 17453
3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
additional information
rubredoxin not mentioned
286367
Pseudomonas putida
?
-
-
-
?
1.14.14.108
additional information
rubredoxin not mentioned
286367
Pseudomonas putida C1 / ATCC 17453
?
-
-
-
?
pH Optimum
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
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
Commentary
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
Cofactor (protein specific)
EC Number
Cofactor
Commentary
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
General Stability (protein specific)
EC Number
General Stability
Organism
1.14.13.51
5-10 vol% ethanol stabilizes the crude cell extract
Rhodococcus
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
Rhodococcus sp.
involved in 1,8-cineole metabolism
6-oxocineole + NAD(P)H
-
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
Rhodococcus sp. C1
involved in 1,8-cineole metabolism
6-oxocineole + NAD(P)H
-
Rhodococcus sp. C1
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
Rhodococcus
?
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
Rhodococcus C1
?
Purification (Commentary) (protein specific)
EC Number
Commentary
Organism
1.14.13.51
partial
Rhodococcus
1.14.14.108
-
Pseudomonas putida
Specific Activity [micromol/min/mg] (protein specific)
EC Number
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
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 (protein specific)
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) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
10% of activity with NADPH over NADH in reverse reaction
286367
Rhodococcus sp.
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
involved in 1,8-cineole metabolism
286367
Rhodococcus sp.
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp.
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
10% of activity with NADPH over NADH in reverse reaction
286367
Rhodococcus sp. C1
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp. C1
r
1.1.1.241
6-endo-hydroxycineole + NAD(P)+
involved in 1,8-cineole metabolism
286367
Rhodococcus sp. C1
6-oxocineole + NAD(P)H
-
286367
Rhodococcus sp. C1
r
1.14.13.51
6-oxocineole + NADPH + O2
-
286367
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
286367
Rhodococcus
?
1.14.13.51
6-oxocineole + NADPH + O2
grown on 1,8-cineole or succinate as carbon source
286367
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
286367
Rhodococcus
?
1.14.13.51
6-oxocineole + NADPH + O2
-
286367
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
286367
Rhodococcus C1
?
1.14.13.51
6-oxocineole + NADPH + O2
grown on 1,8-cineole or succinate as carbon source
286367
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
286367
Rhodococcus C1
?
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
286367
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
286367
Rhodococcus C1
?
-
-
-
?
1.14.14.108
(+)-bornane-2,5-dione + FMNH2 + O2
i.e. 2,5-diketocamphane
286367
Pseudomonas putida
3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O
i.e. cyclopentenoic acid
286367
Pseudomonas putida
?
1.14.14.108
(+)-bornane-2,5-dione + FMNH2 + O2
i.e. 2,5-diketocamphane
286367
Pseudomonas putida C1 / ATCC 17453
3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O
i.e. cyclopentenoic acid
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
(+)-bornanone + FMNH2 + O2
(+)-camphor
286367
Pseudomonas putida
1,2-campholide + FMN + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
(+)-bornanone + FMNH2 + O2
(+)-camphor
286367
Pseudomonas putida C1 / ATCC 17453
1,2-campholide + FMN + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2
6-oxocineole
286367
Pseudomonas putida
1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
1,3,3-trimethyl-2-oxabicyclo-(2,2,2)octane + NADH + O2
6-oxocineole
286367
Pseudomonas putida C1 / ATCC 17453
1,6,6-trimethyl-2,7-dioxa(3,2,2)bicyclononan-3-one + NAD+ + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
6-oxocineole + FMNH2 + O2
-
286367
Pseudomonas putida
3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
286367
Pseudomonas putida
?
1.14.14.108
6-oxocineole + FMNH2 + O2
-
286367
Pseudomonas putida C1 / ATCC 17453
3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid + FMN + H2O
-
286367
Pseudomonas putida C1 / ATCC 17453
?
1.14.14.108
additional information
rubredoxin not mentioned
286367
Pseudomonas putida
?
-
-
-
?
1.14.14.108
additional information
rubredoxin not mentioned
286367
Pseudomonas putida C1 / ATCC 17453
?
-
-
-
?
pH Optimum (protein specific)
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
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