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Information on EC 1.14.14.21 - dibenzothiophene monooxygenase
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1.14.14.21 dibenzothiophene monooxygenaseIUBMB Comments
This bacterial enzyme catalyses the first two steps in the desulfurization pathway of dibenzothiophenes, the oxidation of dibenzothiophene into dibenzothiophene sulfone via dibenzothiophene-5-oxide. The enzyme forms a two-component system with a dedicated NADH-dependent FMN reductase (EC 1.5.1.42) encoded by the dszD gene, which also interacts with EC 1.14.14.22, dibenzothiophene sulfone monooxygenase.
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Word Map
- 1.14.14.21
-
desulfurization
- rhodococcus
- erythropolis
- sulfur
- flavin
-
biodesulfurization
-
two-component
- 2-hydroxybiphenyl
-
fossil
- mononucleotide
-
sulfoxidation
- paenibacillus
-
pet28a
-
dszabc
-
hydrodesulfurization
- desulfinase
-
39-fold
-
sulfur-containing
-
flavin-dependent
-
mesophiles
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
2
+
2
=
+
2
+
2
Synonyms
dibenzothiophene monooxygenase, dbt monooxygenase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BdsC
benzothiophene monooxygenase
BT monooxygenase
cofactor-requiring dibenzothiophene monooxygenase
DBT monooxygenase
DBT-MO
DBT-monooxygenase
dibenzothiophene monooxygenase
dszC
TdsC
DBT monooxygenase
-
dszC
-
-
-
-
dszC
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dibenzothiophene + 2 FMNH2 + 2 O2 = dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
-
dibenzothiophene + FMNH2 + O2 = dibenzothiophene-5-oxide + FMN + H2O
(1a)
-
-
-
dibenzothiophene-5-oxide + FMNH2 + O2 = dibenzothiophene-5,5-dioxide + FMN + H2O
(1b)
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
dibenzothiophene,FMNH2:oxygen oxidoreductase
This bacterial enzyme catalyses the first two steps in the desulfurization pathway of dibenzothiophenes, the oxidation of dibenzothiophene into dibenzothiophene sulfone via dibenzothiophene-5-oxide. The enzyme forms a two-component system with a dedicated NADH-dependent FMN reductase (EC 1.5.1.42) encoded by the dszD gene, which also interacts with EC 1.14.14.22, dibenzothiophene sulfone 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-methyldibenzothiophene + 2 FMNH2 + 2 O2
1-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
2-methyldibenzothiophene + 2 FMNH2 + 2 O2
2-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
3,4,6,7-tetramethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6,7-tetramethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
3,4,6-trimethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6-trimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3,4-benzo-dibenzothiophene + 2 FMNH2 + 2 O2
3,4-benzo-dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
3-ethyldibenzothiophene + 2 FMNH2 + 2 O2
3-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3-methylbenzothiophene + 2 FMNH2 + 2 O2
3-methylbenzothiophene-1,1-dioxide + 2 FMN + 2 H2O
-
-
-
?
3-methylbenzothiophene + FMNH2 + O2
?
-
less than 10% of the activity with dibenzothiophene
-
-
?
3-methyldibenzothiophene + 2 FMNH2 + 2 O2
3-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
4,6-diethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-diethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
5-methylbenzothiophene + 2 FMNH2 + 2 O2
5-methylbenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
5-methylbenzothiophene + FMNH2 + O2
?
-
33% of the activity with dibenzothiophene
-
-
?
7-ethylbenzothiophene + FMNH2 + O2
?
-
less than 10% of the activity with dibenzothiophene
-
-
?
dibenzothiophene + 2 reduced riboflavin + 2 O2
dibenzothiophene-5,5-dioxide + 2 riboflavin + 2 H2O
2,7-diethylbenzothiophene + FMNH2 + O2
?
-
13% of the activity with dibenzothiophene
-
-
?
2,7-diethylbenzothiophene + FMNH2 + O2
?
-
13% of the activity with dibenzothiophene
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
best substrate
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
129% of the activity with dibenzothiophene
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
129% of the activity with dibenzothiophene
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
best substrate
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2-ethylbenzothiophene + FMNH2 + O2
?
-
28% of the activity with dibenzothiophene
-
-
?
2-ethylbenzothiophene + FMNH2 + O2
?
-
28% of the activity with dibenzothiophene
-
-
?
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2-methylbenzothiophene + FMNH2 + O2
?
-
209% of the activity with dibenzothiophene
-
-
?
2-methylbenzothiophene + FMNH2 + O2
?
-
209% of the activity with dibenzothiophene
-
-
?
2-methyldibenzothiophene + 2 FMNH2 + 2 O2
2-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
2-methyldibenzothiophene + 2 FMNH2 + 2 O2
2-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3,4,6,7-tetramethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6,7-tetramethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3,4,6,7-tetramethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6,7-tetramethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3,4-benzo-dibenzothiophene + 2 FMNH2 + 2 O2
3,4-benzo-dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
3,4-benzo-dibenzothiophene + 2 FMNH2 + 2 O2
3,4-benzo-dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
3,4-benzo-dibenzothiophene + 2 FMNH2 + 2 O2
3,4-benzo-dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
3-methyldibenzothiophene + 2 FMNH2 + 2 O2
3-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
3-methyldibenzothiophene + 2 FMNH2 + 2 O2
3-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4,6-diethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-diethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
4,6-diethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-diethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
52% of the activity with dibenzothiophene
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
52% of the activity with dibenzothiophene
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low activity
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
benzothiophene + 2 FMNH2 + 2 O2
benzothiophene-5,5-dioxide + 2 FMN + 2 H2O
best substrate
-
-
?
benzothiophene + 2 FMNH2 + 2 O2
benzothiophene-5,5-dioxide + 2 FMN + 2 H2O
best substrate
-
-
?
benzothiophene + 2 FMNH2 + 2 O2
benzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FADH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FAD + 2 H2O
-
-
-
?
dibenzothiophene + 2 FADH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FAD + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
Gordonia sp. F.5.25.8
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
Mycolicibacterium phlei GTIS10
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low reactivity of TdsC toward dibenzothiophene at high substrate concentrations
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
low reactivity of TdsC toward dibenzothiophene at high substrate concentrations
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
best substrate
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
high activity
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
high activity
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
Rhodococcus erythropolis IGTS8 / ATCC 53968
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
Rhodococcus erythropolis IGTS8 / ATCC 53968
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
overall reaction
-
-
?
dibenzothiophene + 2 FMNH2 + 2 O2
dibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
-
?
dibenzothiophene + 2 reduced riboflavin + 2 O2
dibenzothiophene-5,5-dioxide + 2 riboflavin + 2 H2O
overall reaction, low activity with riboflavin
-
-
?
dibenzothiophene + 2 reduced riboflavin + 2 O2
dibenzothiophene-5,5-dioxide + 2 riboflavin + 2 H2O
overall reaction, low activity with riboflavin
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
Rhodococcus erythropolis IGTS8 / ATCC 53968
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene + FMNH2 + O2
dibenzothiophene-5-oxide + FMN + H2O
-
-
-
?
dibenzothiophene-5,5-dioxide + 2 FMNH2 + O2
2'-hydroxybiphenyl-2-sulfinate + 2 FMN + H2O
-
-
-
?
dibenzothiophene-5,5-dioxide + 2 FMNH2 + O2
2'-hydroxybiphenyl-2-sulfinate + 2 FMN + H2O
Rhodococcus erythropolis IGTS8 / ATCC 53968
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
Rhodococcus erythropolis IGTS8 / ATCC 53968
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
dibenzothiophene-5-oxide + FMNH2 + O2
dibenzothiophene-5,5-dioxide + FMN + H2O
-
-
-
?
thioxanthen-9-one + FMNH2 + O2
?
45% of the activity with dibenzothiophene
-
-
?
thioxanthen-9-one + FMNH2 + O2
?
45% of the activity with dibenzothiophene
-
-
?
additional information
?
-
-
coupled reaction with flavin reductase (TdsD) from thermophilic Paenibacillus sp. strain A11-2. Substrate specificity, overview. No activity with 4,6-di-n-propyl-DBT, 4,6-di-n-butyl-DBT, carbazole, dibenzofuran, fluorene, biphenyl, DBT sulfone, benzothiophene, and naphthothiophene
-
-
?
additional information
?
-
-
the enzyme utilizes aromatic compounds, not having sulfur atoms, as substrates. It acts on indole, converting it to indoxyl and isatin, and its derivatives to form indigoid pigments, and also utilizes indoline and phenoxazine. Indigo derivative formation by BdsC using methylindoles as substrates. Enzyme BdsC exhibits activity toward benzothiophene derivatives but not benzothiophene itself showing a wide reactivity toward aromatic compounds. To measure BdsC activity, flavin reductase (DszD) from another desulfurizing species, Rhodococcus erythropolis strain D-1, is used. Sulfone formations, product analysis by GC-MS
-
-
?
additional information
?
-
-
the enzyme utilizes aromatic compounds, not having sulfur atoms, as substrates. It acts on indole, converting it to indoxyl and isatin, and its derivatives to form indigoid pigments, and also utilizes indoline and phenoxazine. Indigo derivative formation by BdsC using methylindoles as substrates. Enzyme BdsC exhibits activity toward benzothiophene derivatives but not benzothiophene itself showing a wide reactivity toward aromatic compounds. To measure BdsC activity, flavin reductase (DszD) from another desulfurizing species, Rhodococcus erythropolis strain D-1, is used. Sulfone formations, product analysis by GC-MS
-
-
?
additional information
?
-
-
coupled reaction with flavin reductase (TdsD) from thermophilic Paenibacillus sp. strain A11-2. Substrate specificity, overview. No activity with 4,6-di-n-propyl-DBT, 4,6-di-n-butyl-DBT, carbazole, dibenzofuran, fluorene, biphenyl, DBT sulfone, benzothiophene, and naphthothiophene
-
-
?
additional information
?
-
the recombinant enzyme is able to utilize either FMNH2 or FADH2 when coupled with a flavin reductase that reduces either FMN or FAD. Autocatalytic oxidation of reduced flavins, overview
-
-
?
additional information
?
-
the recombinant enzyme is able to utilize either FMNH2 or FADH2 when coupled with a flavin reductase that reduces either FMN or FAD. Autocatalytic oxidation of reduced flavins, overview
-
-
?
additional information
?
-
-
the dszC gene encodes DBT monooxygenase, which catalyzes the conversion of dibenzothiophene to dibenzothiophene sulfone
-
-
?
additional information
?
-
Mycolicibacterium phlei GTIS10
-
the dszC gene encodes DBT monooxygenase, which catalyzes the conversion of dibenzothiophene to dibenzothiophene sulfone
-
-
?
additional information
?
-
substrate specificity of enzyme TsdC with dibenzothiophene derivatives and benzothiophene derivatives, overview. No or poor activity with 4,6-dipropyldibenzothiophene, 4,6-dibutyldibenzothiophene, and 1-methyldibenzothiophene
-
-
?
additional information
?
-
substrate specificity of enzyme TsdC with dibenzothiophene derivatives and benzothiophene derivatives, overview. No or poor activity with 4,6-dipropyldibenzothiophene, 4,6-dibutyldibenzothiophene, and 1-methyldibenzothiophene
-
-
?
additional information
?
-
-
FMN:NADPH oxidoreductase from Vibrio harveyi complements activities of purified DszA and DszC proteins. DszA and DszC are oxygenase units that do not use NAD(P)H directly, but instead use FMNH2 from a FMN:NADPH oxidoreductase for oxygenation. The oxygenase and oxidoreductase units do not interact but exchange electrons, overview. Purified DszC or DszA proteins exhibit no activity in presence of 10 mM FMN, 5 mM NADPH, oxygen, and organosulfur substrates
-
-
?
additional information
?
-
strain KA2-5-1 desulfurizes a variety of alkyl dibenzothiophenes through the specific cleavage of their C-S bonds. In addition, strain KA2-5-1 also attacks alkyl benzothiophenes in a C-S-bond-targeted fashion, substrate specificity overview
-
-
?
additional information
?
-
analysis of the coupled reaction of DszC with the purified NADPH-preferring flavin reductase from Paenibacillus polymyxa A-1, overview
-
-
?
additional information
?
-
coupled assay with endogenous NADH-dependent flavin reductase, EC 1.5.1.36
-
-
?
additional information
?
-
no or poor activity with 3,4-benzo-dibenzothiophene, biphenyl, carbazole, dibenzofuran, and fluorene, substrate specificity, overview. Interaction with purified flavin reductase from the non-DBT-desulfurizing bacterium, Paenibacillus polymyxa A-1, with DszC
-
-
?
additional information
?
-
purified enzyme DszC couples in the reaction with a flavin reductase purified from Bacillus sp. strain DSM411, the flavin reductase reacts with FMN and NADH, but also with NADPH and FAD to a lesser extent
-
-
?
additional information
?
-
the purified monooxygenase, encoded by dszC of KA2-5-1, converts benzothiophene and dibenzothiophene into benzothiophene sulfone and dibenzothiophene sulfone, respectively, with the aid of an NADH-dependent oxidoreductase, substrate specificity overview
-
-
?
additional information
?
-
purified enzyme DszC couples in the reaction with a flavin reductase purified from Bacillus sp. strain DSM411, the flavin reductase reacts with FMN and NADH, but also with NADPH and FAD to a lesser extent
-
-
?
additional information
?
-
coupled assay with endogenous NADH-dependent flavin reductase, EC 1.5.1.36
-
-
?
additional information
?
-
analysis of the coupled reaction of DszC with the purified NADPH-preferring flavin reductase from Paenibacillus polymyxa A-1, overview
-
-
?
additional information
?
-
no or poor activity with 3,4-benzo-dibenzothiophene, biphenyl, carbazole, dibenzofuran, and fluorene, substrate specificity, overview. Interaction with purified flavin reductase from the non-DBT-desulfurizing bacterium, Paenibacillus polymyxa A-1, with DszC
-
-
?
additional information
?
-
Rhodococcus erythropolis IGTS8 / ATCC 53968
-
FMN:NADPH oxidoreductase from Vibrio harveyi complements activities of purified DszA and DszC proteins. DszA and DszC are oxygenase units that do not use NAD(P)H directly, but instead use FMNH2 from a FMN:NADPH oxidoreductase for oxygenation. The oxygenase and oxidoreductase units do not interact but exchange electrons, overview. Purified DszC or DszA proteins exhibit no activity in presence of 10 mM FMN, 5 mM NADPH, oxygen, and organosulfur substrates
-
-
?
additional information
?
-
strain KA2-5-1 desulfurizes a variety of alkyl dibenzothiophenes through the specific cleavage of their C-S bonds. In addition, strain KA2-5-1 also attacks alkyl benzothiophenes in a C-S-bond-targeted fashion, substrate specificity overview
-
-
?
additional information
?
-
the purified monooxygenase, encoded by dszC of KA2-5-1, converts benzothiophene and dibenzothiophene into benzothiophene sulfone and dibenzothiophene sulfone, respectively, with the aid of an NADH-dependent oxidoreductase, substrate specificity overview
-
-
?
additional information
?
-
dibenzothiophene sulfoxide and sulfone obtain their oxygen atom(s) from molecular oxygen rather than water in their formation from dibenzothiophene, isotope labeling. The enzyme also utilizes benzyl sulfide and benzyl sulfoxide as substrates, it is a sulfide/sulfoxide monooxygenase. A flavin reductase FRP coupled assay
-
-
?
additional information
?
-
reduced FMN reacts with an oxygen molecule at C4a position of the isoalloxazine ring, producing the C4a-(hydro)peroxyflavin intermediate which is stabilized by residues H391 and S163. H391 may contribute to the formation of the C4a-(hydro)peroxyflavin by acting as a proton donor to the proximal peroxy oxygen, and it might also be involved in the protonation process of the C4a-(hydro)xyflavin, substrate binding and mechanism, molecular docking
-
-
?
additional information
?
-
dibenzothiophene sulfoxide and sulfone obtain their oxygen atom(s) from molecular oxygen rather than water in their formation from dibenzothiophene, isotope labeling. The enzyme also utilizes benzyl sulfide and benzyl sulfoxide as substrates, it is a sulfide/sulfoxide monooxygenase. A flavin reductase FRP coupled assay
-
-
?
additional information
?
-
reduced FMN reacts with an oxygen molecule at C4a position of the isoalloxazine ring, producing the C4a-(hydro)peroxyflavin intermediate which is stabilized by residues H391 and S163. H391 may contribute to the formation of the C4a-(hydro)peroxyflavin by acting as a proton donor to the proximal peroxy oxygen, and it might also be involved in the protonation process of the C4a-(hydro)xyflavin, substrate binding and mechanism, molecular docking
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
3,4,6,7-tetramethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6,7-tetramethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
3,4,6-trimethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6-trimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3-ethyldibenzothiophene + 2 FMNH2 + 2 O2
3-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4,6-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
4,6-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
4-methyldibenzothiophene + 2 FMNH2 + 2 O2
4-methyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
benzothiophene + 2 FMNH2 + 2 O2
benzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2,8-dimethyldibenzothiophene + 2 FMNH2 + 2 O2
2,8-dimethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
2-ethyldibenzothiophene + 2 FMNH2 + 2 O2
2-ethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-
-
-
?
3,4,6,7-tetramethyldibenzothiophene + 2 FMNH2 + 2 O2
3,4,6,7-tetramethyldibenzothiophene-5,5-dioxide + 2 FMN + 2 H2O
-