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Literature summary for 1.14.14.1 extracted from

  • Dietrich, M.; Eiben, S.; Asta, C.; Do, T.A.; Pleiss, J.; Urlacher, V.B.
    Cloning, expression and characterisation of CYP102A7, a self-sufficient P450 monooxygenase from Bacillus licheniformis (2008), Appl. Microbiol. Biotechnol., 79, 931-940.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
plasmid propagation in Escherichia coli DH5alpha, heterologous expression of CYP102A1, CYP102A2, CYP102A3 and CYP102A7 from vector pET 28a(+) in Escherichia coli BL21 (DE3) Bacillus licheniformis

Inhibitors

Inhibitors Comment Organism Structure
dimethyl sulfoxide CYP102A7 exhibits 50% of its initial activity in the presence of 26% dimethyl sulfoxide Bacillus licheniformis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0041
-
cytochrome c CYP102A7, at pH 7.5 Bacillus licheniformis
0.0118
-
stearic acid CYP102A7, at pH 7.5 Bacillus licheniformis
0.0129
-
12-methyl-tetradecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis
0.0165
-
palmitoleic acid CYP102A7, at pH 7.5 Bacillus licheniformis
0.0165
-
13-methyl-tetradecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis
0.0386
-
hexadecanoic acid CYP102A7, at pH 7.5, highest activity Bacillus licheniformis
0.0509
-
tetradecanoic acid CYP102A7, at pH 7.5, highest activity Bacillus licheniformis
0.0551
-
linoleic acid CYP102A7, at pH 7.5 Bacillus licheniformis
0.102
-
dodecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
120000
-
x * 120000, SDS-PAGE Bacillus licheniformis

Organism

Organism UniProt Comment Textmining
Bacillus licheniformis
-
strain DSM13
-
Bacillus licheniformis DSM 13
-
strain DSM13
-

Purification (Commentary)

Purification (Comment) Organism
CYP102A7 purified by immobilised metal affinity chromatography using the N-terminally attached His6-tag, 6.6fold, ca. 95% pure Bacillus licheniformis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-(+)-limonene + 2 O2 + 2 NADPH CYP102A7, high activity Bacillus licheniformis (R)-cis-1,2-limonene epoxide + cis-carveol + 2 NADP+ + 2 H2O
-
?
(R)-(+)-limonene + 2 O2 + 2 NADPH CYP102A7, high activity Bacillus licheniformis DSM 13 (R)-cis-1,2-limonene epoxide + cis-carveol + 2 NADP+ + 2 H2O
-
?
(S)-(-)-limonene + NADPH + O2 CYP102A7, high activity Bacillus licheniformis (S)-trans-1,2 limonene epoxide + NADP+ + H2O
-
?
(S)-(-)-limonene + NADPH + O2 CYP102A7, high activity Bacillus licheniformis DSM 13 (S)-trans-1,2 limonene epoxide + NADP+ + H2O
-
?
10-p-nitrophenoxydecanoic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
10-p-nitrophenoxydecanoic acid + NADPH + O2 CYP102A7 Bacillus licheniformis DSM 13 ?
-
?
12-methyl-myristic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
12-methyl-tetradecanoic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
13-methyl-myristic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
13-methyl-tetradecanoic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
3 geranylacetone + 3 NADPH + 3 H+ + 3 O2 CYP102A7, high activity Bacillus licheniformis 9,10-epoxygeranylacetone + 11-hydroxygeranylacetone + 5,6-epoxygeranylacetone + 3 NADP+ + 3 H2O
-
?
7-ethoxycoumarin + NADPH + H+ + O2 CYP102A7 catalyses dealkylation, although with activity much lower than towards fatty acids Bacillus licheniformis 7-hydroxycoumarin + NADP+ + H2O + ?
-
?
alpha-ionone + NADPH + O2 CYP102A7, high activity Bacillus licheniformis ?
-
?
arachidonic acid + O2 + NADPH CYP102A7 Bacillus licheniformis 20-hydroxyeicosatetraenoic acid + H2O + NADP+
-
?
arachidonic acid + O2 + NADPH CYP102A7 Bacillus licheniformis DSM 13 20-hydroxyeicosatetraenoic acid + H2O + NADP+
-
?
beta-ionone + NADPH + O2 CYP102A7, high activity Bacillus licheniformis 4-hydroxy-beta-ionone + NADP+ + H2O
-
?
cytochrome c + NADH + H+ + O2
-
Bacillus licheniformis ?
-
r
cytochrome c + O2 + NADH
-
Bacillus licheniformis ?
-
r
dodecanoic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
hexadecanoic acid + NADPH + O2 CYP102A7, highest binding affinity Bacillus licheniformis ?
-
?
lauric acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
linoleic acid + NADPH + O2 CYP102A1, CYP102A2, CYP102A3 and CYP102A7. CYP102A7 with high binding affinity Bacillus licheniformis ?
-
?
additional information CYP102A7 is active towards medium-chain fatty acids but shows a strong preference for saturated over unsaturated fatty acids. Besides fatty acids, CYP102A7 is able to catalyse the oxidation of cyclic and acyclic terpenes with high activity and coupling efficiency. 7-methoxycoumarin is not converted by CYP102A7. No NADPH consumption with 11-deoxycortisol, dextromethorphane, testosterone and cyclic and acyclic alkanes as substrates Bacillus licheniformis ?
-
?
additional information CYP102A7 is active towards medium-chain fatty acids but shows a strong preference for saturated over unsaturated fatty acids. Besides fatty acids, CYP102A7 is able to catalyse the oxidation of cyclic and acyclic terpenes with high activity and coupling efficiency. 7-methoxycoumarin is not converted by CYP102A7. No NADPH consumption with 11-deoxycortisol, dextromethorphane, testosterone and cyclic and acyclic alkanes as substrates Bacillus licheniformis DSM 13 ?
-
?
myristic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
nerylacetone + NADPH + O2 CYP102A7, high activity Bacillus licheniformis 9,10-epoxynerylacetone + 5,6-epoxynerylacetone + NADP+ + H2O
-
?
oleic acid + NADPH + O2 CYP102A1, CYP102A2, CYP102A3 and CYP102A7 Bacillus licheniformis ?
-
?
palmitic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
palmitoleic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
stearic acid + NADPH + O2 CYP102A7 Bacillus licheniformis ?
-
?
tetradecanoic acid + NADPH + O2 CYP102A7, highest activity Bacillus licheniformis ?
-
?

Subunits

Subunits Comment Organism
? x * 120000, SDS-PAGE Bacillus licheniformis

Synonyms

Synonyms Comment Organism
CYP102A1
-
Bacillus licheniformis
CYP102A2
-
Bacillus licheniformis
CYP102A3
-
Bacillus licheniformis
CYP102A7
-
Bacillus licheniformis
P450 monooxygenase
-
Bacillus licheniformis

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
27.5
-
half-life of CYP102A7 at room temperature approximately 100 min. Increased activity (115%) after incubation at 27.5°C, higher temperatures result in a steady loss of activity against tetradecanoic acid. No activity after incubation at 60°C Bacillus licheniformis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
13.9
-
12-methyl-tetradecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis
16.18
-
stearic acid CYP102A7, at pH 7.5 Bacillus licheniformis
21.1
-
13-methyl-tetradecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis
22.8
-
palmitoleic acid CYP102A7, at pH 7.5 Bacillus licheniformis
25.65
-
hexadecanoic acid CYP102A7, at pH 7.5, highest binding affinity Bacillus licheniformis
27.7
-
dodecanoic acid CYP102A7, at pH 7.5 Bacillus licheniformis
29.3
-
linoleic acid CYP102A7, at pH 7.5 Bacillus licheniformis
59.8
-
tetradecanoic acid CYP102A7, at pH 7.5, highest activity Bacillus licheniformis
122.4
-
cytochrome c CYP102A7, at pH 7.5 Bacillus licheniformis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
-
Bacillus licheniformis

pH Stability

pH Stability pH Stability Maximum Comment Organism
6 9 results in a loss of coupling efficiency in the reaction with tetradecanoic acid Bacillus licheniformis

Cofactor

Cofactor Comment Organism Structure
FAD
-
Bacillus licheniformis
FMN
-
Bacillus licheniformis
NADPH
-
Bacillus licheniformis