1.14.14.133: 1,8-cineole 2-endo-monooxygenase
This is an abbreviated version!
For detailed information about 1,8-cineole 2-endo-monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.133
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1.14.14.133
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p450cam
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heme
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monooxygenases
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h-bonding
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citrobacter
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monoterpenes
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fmn
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substrate-bound
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fmn-containing
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braakii
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substrate-free
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monoterpenoid
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sesquiterpene
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s-oxidations
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bicyclic
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terpene
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ferryl
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low-spin
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regioselective
- 1.14.14.133
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p450cam
- heme
- monooxygenases
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h-bonding
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citrobacter
- monoterpenes
- fmn
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substrate-bound
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fmn-containing
- braakii
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substrate-free
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monoterpenoid
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sesquiterpene
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s-oxidations
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bicyclic
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terpene
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ferryl
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low-spin
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regioselective
Reaction
Synonyms
CinA, CYP176A, CYP176A1, EC 1.14.13.156, P450cin
ECTree
1.14.14.133 1,8-cineole 2-endo-monooxygenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.14.133 - 1,8-cineole 2-endo-monooxygenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,8-cineole + [reduced flavodoxin] + O2
(1R)-6beta-hydroxycineole + [oxidized flavodoxin] + H2O
1,8-cineole + [reduced flavodoxin] + O2
6beta-hydroxycineole + [oxidized flavodoxin] + H2O
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?
1,8-cineole + [reduced NADPH-hemoprotein reductase] + O2
2-endo-hydroxy-1,8-cineole + [oxidized NADPH-hemoprotein reductase] + H2O
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?
2,2-dimethylbicyclo[2.2.2]octane + [reduced flavodoxin] + O2
? + [oxidized flavodoxin] + H2O
i.e. cinane
identification of least seven oxidised derivatives
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?
camphane + [reduced flavodoxin] + O2
camphor + [oxidized flavodoxin] + H2O
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main product in presence of excess NADPH, plus epi-camphor at a rate of 3:1, and several minor products
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?
1,8-cineole + [reduced flavodoxin] + O2
(1R)-6beta-hydroxycineole + [oxidized flavodoxin] + H2O
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?
1,8-cineole + [reduced flavodoxin] + O2
(1R)-6beta-hydroxycineole + [oxidized flavodoxin] + H2O
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single product
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?
1,8-cineole + [reduced flavodoxin] + O2
(1R)-6beta-hydroxycineole + [oxidized flavodoxin] + H2O
enzyme displays a high affinity for cineole 1 with KD 0.7 microM, and a large spin state change of the heme iron associated with binding of cineole
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?
additional information
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a hydroxyl group on the substrate is vital, and in its absence catalytic turnover is effectively abolished. In the absence of the ethereal oxygen there is still a significant amount of coupling of the NADPH-reducing equivalents to the formation of oxidised product. The substrate itself is not important in controlling oxygen activation, but is essential for regio- and stereoselective substrate oxidation
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additional information
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P450cin catalyzes the stereoselective hydoxylation of 1,8-cineole to 2beta-hydroxy-1,8-cineole. The two electrons necessary for the conversion of 1,8-cineole to 2beta-hydroxy-1,8-cineole are supplied by NADPH and transferred via a FAD-containing cindoxin reductase (CinB), and an FMN-containing cindoxin (CinC) to the heme iron in the active site of P450cin (CinA). The flow of electrons in this multicomponent P450cin system is from NADPH to Fpr via CinC to CinA
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