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1.14.15.1: camphor 5-monooxygenase

This is an abbreviated version!
For detailed information about camphor 5-monooxygenase, go to the full flat file.

Word Map on EC 1.14.15.1

Reaction

(+)-Camphor
+
reduced putidaredoxin
+
O2
=
(+)-exo-5-hydroxycamphor
+
oxidized putidaredoxin
+
H2O

Synonyms

2-bornanone 5-exo-hydroxylase, bornanone 5-exo-hydroxylase, CamC, camphor 5-exo-hydroxylase, camphor 5-exo-methylene hydroxylase, camphor 5-exohydroxylase, camphor 5-hydroxylase, Camphor 5-monooxygenase, camphor hydroxylase, camphor hydroxylase cytochrome P450cam, camphor methylene hydroxylase, camphor monooxygenase, class I cytochrome P450, CYP101, CYP101A1, CYP101B1, CYP101C1, CYP101D1, CYP101D2, CYP111A2, Cyt P450cam, cytochrome P-450-CAM, cytochrome P450 cam, cytochrome P450(cam), cytochrome p450cam, cytochrome P450cam monooxygenase, d-camphor monooxygenase, D-camphor-exo-hydroxylase, haem mono-oxygenase CYP101, methylene hydroxylase, methylene monooxygenase, moe, oxygenase, camphor 5-mono-, P450cam, P450cam monooxygenase, P450tcu

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.15 With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.15.1 camphor 5-monooxygenase

Substrates Products

Substrates Products on EC 1.14.15.1 - camphor 5-monooxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-alpha-pinene + putidaredoxin + O2
(+)-cis-verbenol + (+)-myrtenol + (+)-verbenone + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(+)-alpha-pinene + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(+)-camphor + O2 + reduced putidaredoxin
(+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(+)-camphor + O2 + reduced putidaredoxin
exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(+)-camphor + putidaredoxin + O2
(R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(+)-camphor + reduced ferredoxin + O2
(+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O
show the reaction diagram
(+)-camphor + reduced putidaredoxin + NADH + H+ + O2
(+)-exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O
show the reaction diagram
(+)-camphor + reduced putidaredoxin + O2
(+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(+)-camphor + reduced putidaredoxin + O2
(R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(+)-camphor + reduced putidaredoxin + O2
borneol + oxidized putidaredoxin + H2O
show the reaction diagram
(+)-exo-5-hydroxycamphor + reduced putidaredoxin + O2
5-oxocamphor + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-(+)-camphor + O2 + reduced putidaredoxin
(+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-(+)-camphor + reduced putidaredoxin + O2
(+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(1R)-5,5-difluorocamphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(1R)-5-exo-methoxycamphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(1R)-5-methylenylcamphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(1R)-camphor + putidaredoxin + O2
5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
(1R)-camphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
(1R)-camphor enol ether + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-camphor N-methyl imine + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-camphor oxime + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-endo-borneol allyl ether + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-endo-borneol methyl ether + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-endo-borneol propyl ether + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-iso-borneol methyl ether + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(1R)-norcamphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(1S)-camphor + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
(4S)-limonene + putidaredoxin + O2
?
show the reaction diagram
-
the 7-position is the major site of hydroxylation by P450cam
-
-
?
(R)-2-ethylhexanol + reduced putidaredoxin + O2
(R)-2-ethylhexanoic acid + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
r
(R)-3-ethylhexanol + putidaredoxin + O2
2-ethylhexanoic acid + 2-ethyl-1,2-hexanediol + 2-ethyl-1,3-hexanediol + 2-ethyl-1,4-hexanediol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
ratio: 50:13:15:8
?
(R)-exo-5-hydroxycamphor + O2 + reduced putidaredoxin
2,5-diketocamphane + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
(S)-2-ethylhexanol + reduced putidaredoxin + O2
(S)-2-ethylhexanoic acid + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
r
(S)-3-ethylhexanol + putidaredoxin + O2
2-ethylhexanoic aicd + 2-ethyl-1,2-hexanediol + 2-ethyl-1,3-hexanediol + 2-ethyl-1,4-hexanediol + oxidized putidaredoxin + H2O
show the reaction diagram
-
the (S)-isomer is turned over 1.4times faster than the (R)-isomer
ratio: 15:53:28:10
?
1,2,4,5-tetrachlorobenzene + putidaredoxin + O2
2,3,5,6-tetrachlorophenol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1,2-campholide + putidaredoxin + O2
5-exo-hydroxy-1,2-campholide + oxidized putidaredoxin + H2O
show the reaction diagram
1,2-dibromo-3-chloropropane + O2 + reduced putidaredoxin
1-bromo-3-chloroacetone + allyl chloride + H2O + putidaredoxin + Br-
show the reaction diagram
-
dehalogenation, bromochloroacetone is the major conversion product when the incubation medium is saturated with oxygen, while allyl chloride is the sole product in the absence of oxygen
a number of bromochloropropene are also formed to a minor extent by an elimination mechanism, product determination
-
?
1,2-dichlorobenzene + putidaredoxin + O2
2,3-dichlorophenol + 3,4-dichlorophenol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1,3,5-trichlorobenzene + putidaredoxin + O2
2,4,6-trichlorophenol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1,3,5-trichlorobenzene + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
1,3-dichlorobenzene + putidaredoxin + O2
2,6-dichlorophenol + 2,4-dichlorophenol + 2,5-dichlorophenol + 2,3-dichlorophenol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1,4-dichlorobenzene + putidaredoxin + O2
2,5-dichlorophenol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1-dehydrocamphor + putidaredoxin + O2
exo-5,6-epoxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
1-ethyl-2-methylbenzene + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
the S-enantiomer is preferred by the wild-type enzyme
-
-
?
1-ethyl-3-methylbenzene + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
the S-enantiomer is preferred by the wild-type enzyme
-
-
?
1-ethyl-4-methylbenzene + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
the S-enantiomer is preferred by the wild-type enzyme
-
-
?
1-methylimidazole + O2 + reduced putidaredoxin
?
show the reaction diagram
-
-
-
?
2-adamantanone + O2 + reduced putidaredoxin
5-hydroxy-2-adamantanone + oxidized putidaredoxin + H2O
show the reaction diagram
3 2-methylpentane + 3 reduced ferreredoxin + O2
2-methyl-pentan-2-ol + 2-methyl-pentan-3-ol + 2-methyl-pentan-4-ol + 3 oxidized ferredoxin
show the reaction diagram
-
52.5% 2-methyl-pentan-2-ol + 13% 2-methyl-pentan-3-ol, and 3% 2-methyl-pentan-4-ol for the wild-type enzyme, 5% + 12% + 30% for the mutant Y96A
-
?
3-chloroindole + O2 + reduced putidaredoxin
isatin + H2O + Cl- + oxidized putidaredoxin + ?
show the reaction diagram
no substrate of wild-type, substrate of mutants E156G/V247F/V253G/F256S, T56A/N116H/D297N and G60S/Y75H
-
-
?
3-chloroperbenzoic acid + O2 + reduced putidaredoxin
?
show the reaction diagram
5,5-difluorocamphor + O2 + reduced putidaredoxin
?
show the reaction diagram
-
-
-
-
?
5,5-difluorocamphor + putidaredoxin + O2
5,5-difluoro-9-hydroxycamphor + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
5-exo-bromocamphor + putidaredoxin + O2
5-ketocamphor + oxidized putidaredoxin + Br- + H2O
show the reaction diagram
-
(+)- and (-)-enantiomer
-
?
5-methylenyl-camphor + O2 + reduced putidaredoxin
?
show the reaction diagram
adamantane + reduced ferreredoxin + O2
1-adamantol + 2-adamantol + oxidized ferredoxin + H2O
show the reaction diagram
-
98% 1-adamantol + 2% 2-adamantol for the wild-type enzyme, 97% + 3% for the mutant Y96A
-
?
adamantanone + O2 + reduced putidaredoxin
?
show the reaction diagram
-
-
-
-
?
adamantanone + putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
adamantenone + reduced putidaredoxin + O2
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene + putidaredoxin + O2
3-hydroxybenzo[a]pyrene + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
beta-ionone + O2 + reduced putidaredoxin
4-hydroxy-beta-ionone + oxidized putidaredoxin + H2O
show the reaction diagram
camphane + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
cyclooctane + reduced ferreredoxin + O2
cyclooctanol + cyclooctanone + oxidized ferredoxin + H2O
show the reaction diagram
-
99% cyclooctanol + 1% cyclooctanone for the wild-type enzyme, 97% + 3% for the mutant Y96A
-
?
DL-camphor + reduced putidaredoxin + NADH + H+ + O2
exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O
show the reaction diagram
-
-
-
?
ethylbenzene + putidaredoxin + O2
1-phenylethanol + oxidized putidaredoxin + H2O
show the reaction diagram
-
at 5% of the reaction with (+)-camphor
ratio of (R)- to (S)-1-phenylethanol produced depends on mutant form
?
fluoranthene + putidaredoxin + O2
3-fluoranthol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
hexane + reduced ferreredoxin + O2
hexan-2-ol + hexan-3-ol + oxidized ferredoxin + H2O
show the reaction diagram
-
56% hexan-2-ol + 44% hexan-3-ol for the wild-type enzyme and mutant Y96A
-
?
imidazole + O2 + reduced putidaredoxin
?
show the reaction diagram
-
-
-
?
indole + O2 + reduced putidaredoxin
3-hydroxyindole + oxidized putidaredoxin + H2O
show the reaction diagram
-
no substrate of the wild-type enzyme, but a good substrate for Y96 mutants, mutant screening, overview
3-hydroxyindole undergoes spontaneous air oxidation to produce the insoluble dye indigo
-
?
isoborneol + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
linalool + O2 + reduced putidaredoxin
8-hydroxy-linalool + oxidized putidaredoxin + H2O
show the reaction diagram
norcamphor + O2 + reduced putidaredoxin
?
show the reaction diagram
-
-
-
-
?
norcamphor + reduced putidaredoxin + O2
?
show the reaction diagram
-
-
-
-
?
norcamphor + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
peracetic acid + O2 + reduced putidaredoxin
?
show the reaction diagram
phenanthrene + putidaredoxin + O2
1-phenanthrol + 2-phenanthrol + 3-phenanthrol + 4-phenanthrol + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
pyrene + putidaredoxin + O2
1-pyrenol + 2-pyrenol + 1,6-pyrenequinone + 1,8-pyrenequinone + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
-
?
thiocamphor + reduced putidaredoxin + O2
? + oxidized putidaredoxin + H2O
show the reaction diagram
-
-
-
?
additional information
?
-