3.1.6.19: (R)-specific secondary-alkylsulfatase (type III)
This is an abbreviated version!
For detailed information about (R)-specific secondary-alkylsulfatase (type III), go to the full flat file.
Word Map on EC 3.1.6.19
Reaction
Synonyms
(R)-specific sec-alkylsulfatase, Pisa1, S3 secondary alkylsulphohydrolase, sec-alkylsulfatase, sulfatase RS2
ECTree
3.1.6.19 (R)-specific secondary-alkylsulfatase (type III)Advanced search results
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Substrates Products on EC 3.1.6.19 - (R)-specific secondary-alkylsulfatase (type III)
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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
(2R)-1-(4-chlorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
(2R)-1-(4-fluorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
(2R)-octan-2-yl hydrogen sulfate + H2O
(S)-2-octanol + sulfate
-
-
-
?
(2R)-1-(4-chlorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
-
enantiomeric excess of the product: 16%
-
-
?
(2R)-1-(4-chlorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
-
enantiomeric excess of the product: 16%
-
-
?
(2R)-1-(4-fluorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
-
enantiomeric excess of the product: 16%
-
-
?
(2R)-1-(4-fluorophenyl)propan-2-yl sulfate + H2O
(2S)-1-(4-chlorophenyl)propan-2-ol + sulfate
-
enantiomeric excess of the product: 16%
-
-
?
(2R)-nonan-2-yl sulfate + H2O
(2S)-nonan-2-ol + sulfate
-
enantiomeric excess of the product: 65%
-
-
?
(2R)-nonan-2-yl sulfate + H2O
(2S)-nonan-2-ol + sulfate
-
enantiomeric excess of the product: 65%
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
enantioselectivity expressed by E-value is 21. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
enantioselectivity expressed by E-value is 21. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
-
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
-
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
high enantioselectivity (E-value > 200), enantiomeric excess > 99
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provided the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl sulfate and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
high enantioselectivity (E-value > 200), enantiomeric excess > 99
-
-
?
(2R)-octan-2-yl sulfate + H2O
(2S)-octan-2-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provided the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl sulfate and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
high enantioselectivity (E-value > 200), enantiomeric excess of the product: > 99%
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
high enantioselectivity (E-value > 200), enantiomeric excess of the product: > 99%
-
-
?
(2S)-1-phenylpropan-2-yl sulfate + H2O
(2S)-1-phenylpropan-2-ol + sulfate
-
-
-
-
?
(3R)-pentan-3-yl sulfate + H2O
pentan-3-ol + sulfate
-
low activity
-
-
?
(4R)-heptan-4-yl sulfate + H2O
(4S)-heptan-4-ol + sulfate
-
the L-isomer is much more readily hydrolysed than the D-isomer. Enzymic hydrolysis of this group is accompanied by complete inversion of configuration at the asymmetric carbon atom
-
-
?
(4R)-heptan-4-yl sulfate + H2O
(4S)-heptan-4-ol + sulfate
-
the L-isomer is much more readily hydrolysed than the D-isomer. Enzymic hydrolysis of this group is accompanied by complete inversion of configuration at the asymmetric carbon atom
-
-
?
(5R)-nonan-5-yl sulfate + H2O
nonan-5-ol + sulfate
-
the L-isomer is much more readily hydrolysed than the D-isomer. Enzymic hydrolysis of this group is accompanied by complete inversion of configuration at the asymmetric carbon atom
-
-
?
(5R)-nonan-5-yl sulfate + H2O
nonan-5-ol + sulfate
-
the L-isomer is much more readily hydrolysed than the D-isomer. Enzymic hydrolysis of this group is accompanied by complete inversion of configuration at the asymmetric carbon atom
-
-
?
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
-
enantioselectivity expressed by E-value is 4.3. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
-
enantioselectivity expressed by E-value is 4.3. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
-
enantiomeric excess of the product: 59%
-
-
?
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provided the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl sulfate and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
rac-octan-3-yl sulfate + H2O
(3S)-octan-3-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provided the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl sulfate and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
-
no enantioselectivity is observed, production of racemic 4-octanol. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
-
no enantioselectivity is observed, production of racemic 4-octanol. The preferred substrates for the enzyme are linear sec-alkyl sulfate esters, particularly 2-, 3-, and 4-octyl sulfates. The enzymatic hydrolysis proceeds through inversion of the configuration at the stereogenic carbon atom
-
-
?
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
-
enantiomeric excess of the product: 55%
-
-
?
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provides the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl- and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
rac-octan-4-yl sulfate + H2O
(4S)-octan-4-ol + sulfate
-
hydrolysis of (R)-enantiomers from the racemate provides the corresponding (S)-configured sec-alcohols. Excellent enantioselectivity is observed for octan-2-yl sulfate. When the sulfate ester moiety is gradually moved toward the center of the molecule (octan-3-yl- and octan-4-yl sulfate), the enantioselectivities decreases, which is due to the fact that the alkyl groups flanking the sulfate ester group became similar in size, thus making the chiral recognition process more difficult
-
-
?
additional information
?
-
-
when rather symmetrical molecules, such as 3- or 4-octyl sulfate, are used, the chiral recognition process gets more difficult as the relative sizes of the two alkyl groups adjacent to the stereogenic sulfate ester group become more similar.
-
-
?
additional information
?
-
-
when rather symmetrical molecules, such as 3- or 4-octyl sulfate, are used, the chiral recognition process gets more difficult as the relative sizes of the two alkyl groups adjacent to the stereogenic sulfate ester group become more similar.
-
-
?
