Information on EC 1.14.14.5 - alkanesulfonate monooxygenase

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The expected taxonomic range for this enzyme is: Escherichia coli

EC NUMBER
COMMENTARY hide
1.14.14.5
-
RECOMMENDED NAME
GeneOntology No.
alkanesulfonate monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an alkanesulfonate + FMNH2 + O2 = an aldehyde + FMN + sulfite + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
desulfonation
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Sulfur metabolism
-
-
two-component alkanesulfonate monooxygenase
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-
non-pathway related
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SYSTEMATIC NAME
IUBMB Comments
alkanesulfonate,FMNH2:oxygen oxidoreductase
The enzyme from Escherichia coli catalyses the desulfonation of a wide range of aliphatic sulfonates (unsubstituted C1- to C14-sulfonates as well as substituted C2-sulfonates). Does not desulfonate taurine (2-aminoethanesulfonate) or aromatic sulfonates. Does not use FMN as a bound cofactor. Instead, it uses reduced FMN (i.e., FMNH2) as a substrate. FMNH2 is provided by SsuE, the associated FMN reductase (EC 1.5.1.38).
CAS REGISTRY NUMBER
COMMENTARY hide
54596-24-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,3-dioxo-2-isoindolineethanesulfonic acid + FMNH2 + O2
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetaldehyd + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
2-(4-pyridyl)ethanesulfonic acid + FMNH2 + O2
pyridin-4-ylacetaldehyde
show the reaction diagram
-
-
-
-
?
4-phenyl-1-butanesulfonic acid + FMNH2 + O2
4-phenylbutanol + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
an alkanesulfonate + FMNH2 + O2
an aldehyde + FMN + sulfite + H2O
show the reaction diagram
an alkansulfonate + FMNH2 + O2
an aldehyde + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
butanesulfonic acid + FMNH2 + O2
butanal + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
decanesulfonic acid + FMNH2 + O2
decanal + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
hexanesulfonic acid + FMNH2 + O2
hexanal + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
MOPS + FMNH2 + O2
?
show the reaction diagram
-
-
-
-
?
N-phenyltaurine + FMNH2 + O2
anilinoacetaldehyde + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
octanesulfonate + FMNH2 + O2
octanal + FMN + sulfite + H2O
show the reaction diagram
octanesulfonic acid + FMNH2 + O2
octanal + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
pentanesulfonic acid + FMNH2 + O2
pentaldehyde + FMN + sulfite + H2O
show the reaction diagram
PIPES + FMNH2 + O2
?
show the reaction diagram
-
-
-
-
?
R-CH2-SO3H + FMNH2 + O2
R-CHO + FMN + sulfite + H2O
show the reaction diagram
-
-
-
?
additional information
?
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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
an alkanesulfonate + FMNH2 + O2
an aldehyde + FMN + sulfite + H2O
show the reaction diagram
an alkansulfonate + FMNH2 + O2
an aldehyde + FMN + sulfite + H2O
show the reaction diagram
-
-
-
-
?
R-CH2-SO3H + FMNH2 + O2
R-CHO + FMN + sulfite + H2O
show the reaction diagram
-
-
-
?
additional information
?
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-
the two-component alkanesulfonate monooxygenase system from Escherichia coli includes an FMN reductase, SsuE, and an FMNH2-dependent alkanesulfonate monooxygenase, SsuD, involved in the acquisition of sulfur from alkanesulfonates during sulfur starvation, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.114
1,3-dioxo-2-isoindolineethanesulfonic acid
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0.139
2-(4-pyridyl)ethanesulfonic acid
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0.11
4-phenyl-1-butanesulfonic acid
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0.87
butanesulfonic acid
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0.035
decanesulfonic acid
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0.095
hexanesulfonic acid
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-
0.617
MOPS
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-
0.237
N-phenyltaurine
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-
0.0075 - 0.044
octanesulfonate
0.044
octanesulfonic acid
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0.189
pentanesulfonic acid
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1.11
PIPES
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-
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.093 - 0.86
octanesulfonate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.3 - 63.3
octanesulfonate
11917
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
assay at
9.1
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in 10 mM Tris-HCl
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
30
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enzyme assay
PDB
SCOP
CATH
ORGANISM
UNIPROT
Escherichia coli (strain K12)
Escherichia coli (strain K12)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
41200
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4 * 41200, SDS-PAGE
41605
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4 * 41605, mass spectrometry
181000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotetramer
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4 * 41200, SDS-PAGE
tetramer
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4 * 41605, mass spectrometry
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
X-ray characterization, tetramer 96 A x 90 A x 66 A, comprises two homodimers, monomer 60A x 50 A x 40 A, TIM-barrel protein
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 15% glycerol, the activity increases slightly during the first 2 to 3 weeks of storage
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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gene ssuD, the alkanesulfonate monooxygenase system, expressed from the ssuEADCB operon, is comprised of a flavin reductase encoded by ssuE and monooxygenase encoded by ssuD, ssuD expressionin strain BL21(DE3)
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ligated into pET21a plasmid containing the ssuD gene, wild-type and mutants expressed in Escherichia coli BL21(DE3) super-competent cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C54A
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has little effect on FMN or FMNH2 binding, kcat/Km value decreases 6fold relative to wild-type
C54S
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has little effect on FMN or FMNH2 binding, kcat/Km value increases 3fold relative to wild-type. Is able to generate the C4a-(hydro)peroxyflavin, but the rate of formation is increased 10fold relative to wild-type
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