Information on EC 3.1.6.19 - (R)-specific secondary-alkylsulfatase

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

EC NUMBER
COMMENTARY hide
3.1.6.19
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RECOMMENDED NAME
GeneOntology No.
(R)-specific secondary-alkylsulfatase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an (R)-secondary-alkyl sulfate + H2O = an (S)-secondary-alcohol + sulfate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
non-pathway related
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SYSTEMATIC NAME
IUBMB Comments
(R)-secondary-alkyl sulfate sulfohydrolase [(S)-secondary-alcohol forming]
The enzyme from Rhodococcus ruber is involved in the biodegradation of alkyl sulfate esters used as detergents and released into the environment. The prefered substrates are linear secondary-alkyl sulfate esters, particularly octan-2-yl, octan-3-yl, and octan-4-yl sulfates [1]. The enzyme from Pseudomonas sp. DSM6611 utilizes a range of secondary-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities are obtained for substrates bearing groups of different size adjacent to the sulfate moiety [4]. The enzymic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom [1,4]. The enzyme contains a Zn2+ ion [3].
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-1-(4-chlorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
show the reaction diagram
(2R)-1-(4-fluorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
show the reaction diagram
(2R)-nonan-2-yl sulfate + H2O
(2S)-nonan-2-ol + sulfate
show the reaction diagram
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
show the reaction diagram
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
show the reaction diagram
(3R)-pentan-3-yl sulfate + H2O
(3S)-pentan-3-ol + sulfate
show the reaction diagram
(4R)-heptan-4-yl sulfate + H2O
(4S)-heptan-4-ol + sulfate
show the reaction diagram
(5R)-nonan-5-yl sulfate + H2O
nonan-5-ol + sulfate
show the reaction diagram
(R)-2-octyl sulfate + H2O
(S)-2-octanol + sulfate
show the reaction diagram
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
show the reaction diagram
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
show the reaction diagram
additional information
?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
decan-5-yl sulfate
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octan-5-yl sulfate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
40
(3R)-pentan-3-yl sulfate
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pH 7.5, 30C
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15
(4R)-heptan-4-yl sulfate
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pH 7.5, 30C
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1.5
(5R)-nonan-5-yl sulfate
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pH 7.5, 30C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.4
decan-5-yl sulfate
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pH 7.5, 30C
43
octan-5-yl sulfate
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pH 7.5, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9
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pH 7.5, 30C
124.3
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pH 7.5, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
8.2
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hydrolysis of heptan-4-yl sulfate and nonan-5-yl sulfate
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9.2
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5.0: about of 40% of maximal activity with nonan-5-yl sulfate, about 80% of maximal activity with heptan-4-yl sulfate. pH 9.2: about 55% of maximal activity with nonan-5-yl sulfate
6.5 - 9
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pH 6.5: about 55% of maximal activity, pH 9.0: about 50% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 30
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20C: about 50% of maximal activity, 30C: optimum, 35C: about 25% of maximal activity, no activity at 40C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.1
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isoelectric focusing
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
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gel filtration
43000
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1 * 43000, SDS-PAGE
46000
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polyacrylamide gel under non-denaturing conditions
67000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis