Information on EC 1.14.15.3 - alkane 1-monooxygenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.14.15.3
-
RECOMMENDED NAME
GeneOntology No.
alkane 1-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
octane + 2 reduced rubredoxin + O2 + 2 H+ = 1-octanol + 2 oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
-
-
Caprolactam degradation
-
-
Fatty acid degradation
-
-
Metabolic pathways
-
-
octane oxidation
-
-
Retinol metabolism
-
-
octane oxidation
-
-
SYSTEMATIC NAME
IUBMB Comments
alkane,reduced-rubredoxin:oxygen 1-oxidoreductase
Some enzymes in this group are heme-thiolate proteins (P-450). Also hydroxylates fatty acids in the omega-position.
CAS REGISTRY NUMBER
COMMENTARY hide
9059-16-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain EB104
SwissProt
Manually annotated by BRENDA team
strain EB104
SwissProt
Manually annotated by BRENDA team
genes alkB1, alkB2, p450 and almA
-
-
Manually annotated by BRENDA team
genes alkB1, alkB2, p450 and almA
-
-
Manually annotated by BRENDA team
strain ATCC22711
-
-
Manually annotated by BRENDA team
strain ATCC22711
-
-
Manually annotated by BRENDA team
strain EH15
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain 7E1C
-
-
Manually annotated by BRENDA team
strain 7E1C
-
-
Manually annotated by BRENDA team
strain MT-811
-
-
Manually annotated by BRENDA team
strain T70
-
-
Manually annotated by BRENDA team
fragment
SwissProt
Manually annotated by BRENDA team
strain TF6
-
-
Manually annotated by BRENDA team
strain EH15D
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
fragment; strain HXN-1000
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-1000
SwissProt
Manually annotated by BRENDA team
fragment; strain ATCC 12670
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-600
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-600
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-100
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-100
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-1900; fragment; strain HXN-500
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-1900
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-500
SwissProt
Manually annotated by BRENDA team
strain H37Rv AH
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain CF8
-
-
Manually annotated by BRENDA team
strain CF8
-
-
Manually annotated by BRENDA team
fragment; strain HXN-1400
SwissProt
Manually annotated by BRENDA team
fragment; strain HXN-1400
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain S7B1
-
-
Manually annotated by BRENDA team
2 isoforms
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
fragment; strain NRRL B-16531
SwissProt
Manually annotated by BRENDA team
fragment; strain NRRL B-16531
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
show the reaction diagram
1,1-diethylcyclopropane + NADPH + H+ + O2
?
show the reaction diagram
1,7-octadiene + NADH + H+ + O2
1,2-epoxy-7-octene + NAD+ + H2O
show the reaction diagram
-
epoxidation of simple, aliphatic terminal olefins
-
-
?
1-hexadecene + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
1-octadecene + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
1-octene + reduced rubredoxin + O2
1,2-epoxyoctane + oxidized rubredoxin + H2O
show the reaction diagram
11-hydroxyeicosatetraenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
2,5-dimethylhexane + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
20-hydroxyeicosatetraenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
5,8,11-eicosatrienoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
8-hydroxyeicosatetraenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
9,10-epoxystearic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
show the reaction diagram
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyeicosatetraenoic acid + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
show the reaction diagram
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
bicyclohexane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
i.e. bicyclo[3.1.0]hexane, no distinction between the 2- and 3-positions, reaction via formation of a substrate radical that persists in the active site
-
-
?
butane + NADPH + H+ + O2
1-butanol + NADP+ + H2O
show the reaction diagram
coronaric acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
cycloheptane + NAD(P)H + H+ + O2
cycloheptanol + NAD(P)+ + H2O
show the reaction diagram
cyclohexane + NAD(P)H + H+ + O2
cyclohexanol + NAD(P)+ + H2O
show the reaction diagram
cyclohexane + NADH + H+ + O2
cyclohexanol + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
cyclooctane + NAD(P)H + H+ + O2
cyclooctanol + NAD(P)+ + H2O
show the reaction diagram
cyclopentane + NAD(P)H + H+ + O2
cyclopentanol + NAD(P)+ + H2O
show the reaction diagram
-
very poor substrate
-
-
?
decane + reduced rubredoxin + O2
1-decanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
docosahexaenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
dodecane + reduced rubredoxin + O2
1-dodecanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
eicosapentaenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
ethyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + acetaldehyde
show the reaction diagram
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O
show the reaction diagram
heptadecane + reduced rubredoxin + O2
1-heptadecanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
hexadecane + reduced rubredoxin + O2
1-hexadecanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
hexane + reduced rubredoxin + O2
1-hexanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
lauric acid + NAD(P)H + H+ + O2
12-hydroxydodecanoic acid + NAD(P)+ + H2O
show the reaction diagram
lauric acid + NADPH + H+ + O2
12-hydroxydodecanoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
lauric acid + NADPH + H+ + O2
12-hydroxylauric acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
lecithin + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
leukotriene B4 + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
linoleic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
linolenic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
methane + NADPH + H+ + O2
methanol + NADP+ + H2O
show the reaction diagram
methane sulfonic acid + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
methyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O
show the reaction diagram
methyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
methylcyclohexane + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
methylphenylcyclopropane + reduced rubredoxin + O2
1-phenylbut-3-en-1-ol + oxidized rubredoxin + H2O
show the reaction diagram
-
reaction via formation of a substrate radical that persists in the active site
-
-
?
monoolein + NADH + H+ + O2
18-hydroxyoctadec-9-enoic acid 2,3-dihydroxypropyl ester + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
myristic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
CYP4V2 is a selective omega-hydroxylase of saturated, medium-chain fatty acids with relatively high catalytic efficiency toward myristic acid
-
-
?
n-alkane + NAD(P)H + H+ + O2
n-alkanol + NAD(P)+ + H2O
show the reaction diagram
n-alkane + NADPH + H+ + O2
n-alkanol + NADP+ + H2O
show the reaction diagram
n-butane + NADPH + H+ + O2
n-butanol + NADP+ + H2O
show the reaction diagram
n-hexadecane + NADPH + H+ + O2
n-hexadecanol + NADP+ + H2O
show the reaction diagram
n-octane + NADH + H+ + O2
n-octanol + NAD+ + H2O
show the reaction diagram
n-octane + reduced rubredoxin + O2
n-octanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
nitromethane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
norcarane + NADPH + H+ + O2
?
show the reaction diagram
norcarane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
show the reaction diagram
-
i.e. bicyclo[4.1.0]heptane, oxidation preferentially occurs at the less sterically hindered 3-position, reaction via formation of a substrate radical that persists in the active site
-
-
?
octadecane + reduced rubredoxin + O2
1-octadecanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
octane + reduced rubredoxin + O2
1-octanol + oxidized rubredoxin + H2O
show the reaction diagram
palmitic acid + NAD(P)H + H+ + O2
16-hydroxyhexadecanoic acid + NAD(P)+ + H2O
show the reaction diagram
palmitic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pentadecane + reduced rubredoxin + O2
1-pentadecanol + oxidized rubredoxin + H2O
show the reaction diagram
-
best substrate
-
-
?
pentane + reduced rubredoxin + O2
1-pentanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
phosphatidylethanolamine + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
phosphatidylserine + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
propane + NADPH + H+ + O2
1-propanol + NADP+ + H2O
show the reaction diagram
propane + NADPH + H+ + O2
propan-1-ol + NADP+ + H2O
show the reaction diagram
Q08KD8 and Q08KD7 andQ08KD6 and Q08KD5, Q08KE2 and Q08KE1 andQ08KD0 and Q08KE9, Q08KE2 and Q08KE1 andQ08KE0 and Q08KD9
-
-
-
?
propane + NADPH + H+ + O2
propanol + NADP+ + H2O
show the reaction diagram
prostaglandin A1 + NADPH + O2
?
show the reaction diagram
prostaglandin A2 + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
prostaglandin E1 + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
spirooctane + NADPH + H+ + O2
?
show the reaction diagram
stearic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
suberin + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
tert-amyl methyl ether + NAD(P)H + H+ + O2
tert-amyl-alcohol + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
tetracosane + reduced rubredoxin + O2
1-tetracosanol + oxidized rubredoxin + H2O
show the reaction diagram
-
-
-
-
?
vernolic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
n-alkane + NAD(P)H + H+ + O2
n-alkanol + NAD(P)+ + H2O
show the reaction diagram
n-alkane + NADPH + H+ + O2
n-alkanol + NADP+ + H2O
show the reaction diagram
octane + reduced rubredoxin + O2
1-octanol + oxidized rubredoxin + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ferredoxin
-
Rieske-type alkane monooxygenase with Rieske-type [2Fe-2S]2 center
-
NAD(P)+
-
-
NAD(P)H
NAD+
-
very little activity at 1 mM level
rubredoxin
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Al3+
-
activates
Cu
-
0.03 atoms per 42000 g/mol peptide
Iron
-
required, diiron enzyme
additional information
-
no or poor effects by Na and K+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(E)-N'-(4-butyl-2-methylphenyl)-N-hydroxyformimidamide
1,1-dichloroethene
-
50% of BMO activity is irreversibly lost after oxidation of approximately 25 nmol/mg protein
1,2-cis-dichloroethene
-
50% of BMO activity is lost after oxidation of 120 nmol/mg protein
1,2-trans-dichloroethene
-
50% of BMO activity is lost after oxidation of 20 nmol/mg protein
1,7-octadiyne
-
inhibits oxidation of methyl tert-butyl ether; putative mechanism-based inactivator, strongly inhibitory at 0.1% (v/v)
1-octyne
-
acts as a mechanism-based inhibitor of AlkB
11-dodecynoic acid
17-octadecynoic acid
8-hydroxyquinoline
diethyldithiocarbamate
-
reduces activity to 88%
Fe2+
-
in 0.5 mM concentration, 100% inhibition
Hg2+
-
0.1 mM concentration, 100% inhibition
menadione
-
-
n-alkanes
-
C5-C10 inhibits oxidation of methyl tert-butyl ether, weaker inhibition at longer chain length
n-butane
-
inhibits oxidation of methyl tert-butyl ether
n-decane
-
0.1% (v/v)
n-decyl-beta-D-maltopyranoside
-
-
n-dodecane
-
0.1% (v/v)
n-dodecyl-beta-D-maltopyranoside
-
-
n-dodecyl-N,N-dimethylamine-n-oxide
-
-
n-heptane
-
0.1% (v/v)
n-hexane
-
0.1% (v/v)
N-hydroxy-N'-(4-n-butyl-2-methylphenyl)formamidine
-
HET0016, a potent and selective inhibitor of CYP omega-hydroxylase, significantly inhibits myocardial apoptosis. Pretreatment with PD98059, the inhibitor of ERK1/2, but not SB203580 or SP600125, almost completely blocks the effect exerted by HET0016. Exogenous 20-hydroxyeicosatetraenoic acid administration exerts opposite effects
N-methylsulfonyl-12, 12-dibromododec-11-enamide
-
a selective CYP omega-hydroxylase inhibitor, significantly inhibits myocardial apoptosis
N-methylsulfonyl-12,12-dibromododec-11-enamide
n-nonane
-
0.1% (v/v)
n-octane
-
0.1% (v/v)
n-pentane
-
0.1% (v/v)
octyl glucose neopentyl glycol
-
-
p-chloromercuribenzoate
-
0.1 mM concentration, 51% inhibition
propane
-
inhibits oxidation of methyl tert-butyl ether
propionate
-
0.01 mM, strong inhibition
retinoic acid
-
0.005 mM, 56% reduction of activity
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-butanol
-
2 mM
Butyraldehyde
-
2 mM
dilauroylphosphatidylcholine
-
needs detergent
Emulgen 911
-
needs detergent 0.3%
-
Emulgen 913
-
needs detergent 0.1%
Phospholipid
-
enhances enzyme activity
Triton X-100
-
needs detergent, 0.04%
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
1-octene
pH 7.4, 30C, recombinant enzyme
0.228
arachidonic acid
-
-
0.58
decane
-
-
5.2
Heptanoate
-
-
22
hexanoate
-
-
0.032 - 0.057
laurate
0.029 - 0.16
lauric acid
0.065
myristic acid
-
-
0.69
Nonanoate
-
-
0.77
Octane
-
-
0.43
palmitic acid
-
-
0.0182
pentadecane
-
pH 7.5, 30C, recombinant alkane hydroxylase large subunit
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0025 - 2.33
arachidonic acid
0.0267 - 2.67
laurate
0.0085 - 0.163
lauric acid
0.013
palmitate
Homo sapiens
-
omega-hydroxylation
0.0105 - 0.0367
palmitic acid
0.00133
PGA1
Homo sapiens
-
omega-hydroxylation
0.183 - 0.417
prostaglandin E1
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.037
n-butane
-
inhibits oxidation of methyl tert-butyl ether
0.192
propane
-
inhibits oxidation of methyl tert-butyl ether
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000038
(E)-N'-(4-butyl-2-methylphenyl)-N-hydroxyformimidamide
Homo sapiens
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00012
-
using ethyl tert-butyl ether as a substrate
0.00313
-
using tert-amyl methyl ether as a substrate
0.0077
-
pH 7.0, 30C
0.00773
-
using methyl tert-butyl ether as a substrate
0.57
-
H318A mutant enzyme, 22C
0.67
-
H308A mutant enzyme, 22C
1.11
-
H163A mutant enzyme, 22C
1.23
-
hydroxylation of octane
1.75
-
epoxidation of 1,7-octadiene
2.03
-
native enzyme, 22C
6.5
-
hydroxylation of lauric acid
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
-
assay conditions
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7 - 7.5
-
laurate hydroxylation in Tris buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperature
25
-
assay conditions
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
second antennal segment, only males
Manually annotated by BRENDA team
-
at the base of machrochaetae, only males
Manually annotated by BRENDA team
-
CYP4A11 is one of the major kidney CYP4 P450s
Manually annotated by BRENDA team
elevated expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
guard cells in the epidermis
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40100
-
x * 40100, amino acid composition
42000
-
x * 42000, SDS-PAGE
46000
-
x * 46000, recombinant Strep-tagged AlkB, SDS-PAGE
52000
-
Western blot analysis
56500
-
gene expression CYP52A4, SDS-PAGE
58000
-
Western blot analysis
59800
-
gene expression CYP52A3, amino acid composition
61800
-
gene expression CYP52A4, amino acid composition
118000
-
SDS-PAGE
150000
-
above, native enzyme, gel filtration
160000
-
recombinant His6-tagged alkane hydroxylase large subunit, native PAGE
800000
-
gel filtration
2000000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
5% carbohydrate
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2D crystallization
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65
-
purified recombinant enzyme, 15 min, inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
after 24 h 15 mM EDTA 60% activity and iron retained
-
after 4 h 15 mM EDTA and 10 mM dithionite 10% activity and iron retained
-
treatment with 0.1 M EDTA and 0.1 M dithionite reduces activity to 10%
-
treatment with sodium cholate and subsequent precipitation with ammonium sulfate reduces activity to 40%
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 1 month, under 50% activity retained
-
-20C, loss of 30% activity by freezing and subsequent thawing
-
-30C, 1 month, loss of 50% activity towards prostaglandin A1
-
-30C, 3 years, no loss of activity towards laurate
-
-70C, 12 days, over 90% activity retained
-
-70C, 6 months, over 50% activity retained
-
4C, 5 days, under 50% activity retained
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme is solubilized from membranes and further purified by anion exchange chromatography and gel filtration
-
recombinant C-terminally StrepII-tagged AlkB from membranes of Escherichia coli strain NovaBlue by detergent solubilization, and Strep-tag affinity chromatography
recombinant enzyme
-
recombinant His6-tagged enzyme system components from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
-
recombinant Strep-tagged enzyme from Escherichia coli strains BL21(DE3), C41(DE3), Rosetta-2(DE3), pLysS, and BL21-CondonPlus(DE3)-RIPL by Strep-tag affinity chromatography, ultrafiltration, and gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
alkB genes expressed in Escherichia coli und Pseudomonas fluorescence; alkB genes expressed in Escherichia coli und Pseudomonas fluorescence; alkB genes expressed in Escherichia coli und Pseudomonas fluorescence; alkB genes expressed in Escherichia coli und Pseudomonas fluorescence
all components of the alkane ydroxylase system expressed in Escherichia coli TOP10
-
baculovirus expressed human CYP4A11
-
CYP86B1-YFP fusion protein expressed under the control of the 35S promoter in a transient expression assay in Nicotiana benthamiana leaves. ProCYP86B1::GUS transgenic plants
expressed from pFastbacCYP4V2HIS vector in Escherichia coli DH10Bac. Hexahistidine-tagged CYP4V2 is expressed in Sf-9 cells after infection with the recombinant baculovirus
-
expressed in Escherichia coli , human gene CYP4AII
-
expressed in Escherichia coli BL21(DE3)pLysS
-
expressed in Escherichia coli strain XL1 and SCS1
-
expressed in Escherichia coli XL-1 blue, human gene CYP4A1
-
expressed in Escherichia coli, genes CYP4A1, CYP4A2, CYP4A3 and CYP4A8
-
expressed in Escherichia coli, human gene CYP4A11
-
expressed in Pseudomonas fluorescence KOB2delta1
expressed in Pseudomonas putida strain GPo12
expressed in Saccharomyces cerevisiae strain GRF18
-
expressed in Saccharomyces cerevisiae strain WAT11
-
gene alkB, expression of C-terminally StrepII-tagged AlkB in membranes of Escherichia coli strain NovaBlue
gene alkB, expression of Strep-tagged enzyme in Escherichia coli strains BL21(DE3), C41(DE3), Rosetta-2(DE3), pLysS, and BL21-CondonPlus(DE3)-RIPL under different growth conditions
-
gene alkW1, DNA and amino acid sequence determination and analysis, genetic organization, sequence comparisons and phylogenetic analysis, quantitative RT-PCR expression analysis, heterologous expression of alkW1 in alkB-deficient P.seudomonas fluorescens and functional complementation; gene alkW2, DNA and amino acid sequence determination and analysis, genetic organization, sequence comparisons and phylogenetic analysis, quantitative RT-PCR expression analysis
genes alkB1, alkB2, p450 and almA, DNA and amino acid sequence determination and analysis, genetic organization, sequence comparisons and phylogenetic analysis, one copy of alkB1 in the B-5 chromosome. Expression of genes alkB1, alkB2, p450 and almA in Pseudomonas putida GPo12 pGEc47DELTAB or Pseudomonas fluorescens KOB2DELTA1, quantitative real-time RT-PCR expression analysis
-
recombinant expression of His6-tagged enzyme system components in Escherichia coli strain BL21(DE3)
-
the 1.4 kb putative promoter region upstream of the predicted CYP86A1 start codon fused in frame to the beta-glucuronidase gene and used to transform wild-type Arabidopsis under the control of the native promoter. Transgenic expression of CYP86A1 fused to GFP, CYP86A1:GFP heterologously and transiently expressed under the control of the CaMV35S-promoter in the epidermis of Nicotiana benthamiana leaves
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP4A gene is altered in both lipid and inflammatory disorders, modest 2fold induction of the CYP4A11 gene by peroxisome proliferator in primary human hepatocytes
-
CYP4F3B gene expression is up-regulated by prostaglandin A1 in a dose- and time-dependent manner. 3fold increase of CYP4F3B protein following treatment of HepaRG cells with 0.02 mM prostaglandin A1 for 24 h
-
expression of prm gene clusters in is induced by gaseous n-alkanes (C2-C4) except methane; expression of prm gene clusters in Mycobacterium sp. TY-6 is induced by gaseous n-alkanes (C2C4) except methane; expression of prm gene clusters in Pseudonocardia sp. TY-7 is induced by gaseous n-alkanes (C2-C4) except methane; expression of prm gene clusters in Pseudonocardia sp. TY-7 is induced by gaseous n-alkanes (C2-C4) except methane
Q08KD8 and Q08KD7 andQ08KD6 and Q08KD5, Q08KE2 and Q08KE1 andQ08KD0 and Q08KE9, Q08KE2 and Q08KE1 andQ08KE0 and Q08KD9
genes alkB1, alkB2, p450 and almA are induced by alkanes ranging from C8 to C36, overview. Thereby the expression of the p450 and almA genes is only upregulated in the presence of medium-chain (C8-C16) or long-chain (C22-C36) n-alkanes, respectively, while alkB1 and alkB2 respond to both medium- and long-chain n-alkanes (C12-C26). Branched alkanes, like pristane and phytane, significantly elevate alkB1 and almA expression levels
in humans, the CYP4A11 gene is not induced by peroxisome proliferators
-
in the female labial palps, expression is weaker and restricted to a smaller area when compared to males
-
induction of alkW1 by n-alkanes ranging in length from 6 to 40 carbon atoms as sole carbon sources
induction of CYP4A genes by starvation (60-700fold), by peroxisome proliferators (30-70fold), ethanol, high fat diet (2.5-100fold), and in diabetes and steatohepatitis. Dramatic induction of both the mouse CYP4A10 and CYP4A14 genes in CYP2E1 knockout mice, which accounts for the increased reactive oxygen species that induce lipid peroxidation
-
no induction of alkW2 by n-alkanes ranging in length from 6 to 40 carbon atoms as sole carbon sources
similar to sxe1 mRNA, expression of SXE1 protein in males oscillates in a diurnal fashion, with highest protein levels occurring around midnight
-
siRNA-mediated-silencing of CYP4F3 suppresses both 20-hydroxyeicosatetraenoic acid synthesis and prostaglandin A1 induced 20-hydroxyeicosatetraenoic acid production
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D323E
-
gene CYP4A1
E320A
-
gene CYP4A1
E320A/D323E
-
gene CYP4A1
L69F
-
oxidizes only C10 and C11 alkanes
L69W
-
oxidizes only C10 and C11 alkanes
L69F
-
oxidizes only C10 and C11 alkanes
-
L69W
-
oxidizes only C10 and C11 alkanes
-
H206Y
-
gene CYP4A7
H206Y/S255F
-
gene CYP4A7
R90W
-
gene CYP4A7
R90W/W93S
-
gene CYP4A7
S255F
-
gene CYP4A7
W93S
-
gene CYP4A7
H138A
-
no activity
H142A
-
no activity
H163A
-
~50% of activity
H168A
-
no activity
H172A
-
no activity
H173A
-
no activity
H181A
-
no activity
H308A
-
~30% of activity
H312A
-
no activity
H315A
-
no activity
H316A
-
no activity
H318A
-
~25% of activity
H273A
-
no activity
H273Q
-
no activity
W55C
-
prefers C11-C13 alkanes as growth substrates
W55S
-
prefers C11-C13 alkanes as growth substrates
H273A
-
no activity
-
H273Q
-
no activity
-
W55C
-
prefers C11-C13 alkanes as growth substrates
-
W55S
-
prefers C11-C13 alkanes as growth substrates
-
additional information