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(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
mechanism
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
the stereochemistry of the product obtained from racemic 2-brompropionic acid by the action of celite-immobilized disrupted cells in dimethylsulfoxid differs from that of the enantiomer obtained in an aqueous buffer
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
Asp10 of the enzyme functions as a catalytic nucleophile: the residue attacks the alpha-carbon of the substrate to form an ester intermediate, which is subsequently hydrolysed to release the product
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
Asp10 of the enzyme functions as a catalytic nucleophile: the residue attacks the alpha-carbon of the substrate to form an ester intermediate, which is subsequently hydrolysed to release the product
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
functional residue: Asp 10
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
acts on acids of short chain lengths, C2 to C4 with inversion at C2
-
-
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
reaction mechanism, overview
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
structure-function analysis, catalytic mechanism, modeling. Asp181 is proposed to participate in the activation of the catalytic water molecule required for hydrolysis of the ester intermediate, Asp186 and Lys157 in DehRhb are responsible for deprotonation of the catalytic water molecule in the second part of the enzyme reaction. In DehRhb, the catalytic water molecule is coordinated by His183 and the conserved Asp186. This residue makes an ion pair with the conserved Lys157. The His183 makes an H-bond with the catalytic Asp18 on one side and an ion pair with Glu21 on the other side. This forms a catalytic triad similar to that observed in the haloalkane dehalogenases
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
it is hypothesized that, in DehL, catalysis is initiated by a nucleophilic attack launched by the side-chain carboxyl of Asp13 on the C2 of L-2CP to form an ester intermediate, which is subsequently hydrolyzed by a water molecule activated by His184 followed by product release
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
reaction mechanism, overview
-
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
mechanism
-
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
Asp10 of the enzyme functions as a catalytic nucleophile: the residue attacks the alpha-carbon of the substrate to form an ester intermediate, which is subsequently hydrolysed to release the product
-
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
Asp10 of the enzyme functions as a catalytic nucleophile: the residue attacks the alpha-carbon of the substrate to form an ester intermediate, which is subsequently hydrolysed to release the product
-
-
(S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
the stereochemistry of the product obtained from racemic 2-brompropionic acid by the action of celite-immobilized disrupted cells in dimethylsulfoxid differs from that of the enantiomer obtained in an aqueous buffer
-
-
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(R,S)-2-bromopropionic acid + H2O
(S)-lactic acid + (S)-2-bromopropionic acid + HCl
-
-
-
-
?
(R,S)-2-chloropropionic acid + H2O
(S)-lactic acid + (S)-2-chloropropionic acid + HCl
(S)-2-bromopropionic acid + H2O
(R)-2-hydroxypropionate + bromide
-
-
-
?
(S)-2-bromopropionic acid + H2O
(R)-2-hydroxypropionic acid + bromide
(S)-2-chlorobutyric acid + H2O
(R)-2-hydroxybutyric acid + chloride
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionate + chloride
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionic acid + chloride
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionate + chloride
-
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
(S)-2-chloropropionic acid + H2O
?
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
1,2-dichloroethane + H2O
?
2,2-dichloropropionate + H2O
propionate + HCl
2,2-dichloropropionic acid + H2O
?
-
-
-
-
?
2,2-dichloropropionic acid + H2O
propionate + 2 HCl
-
-
-
?
2,2-dichloropropionic acid + H2O
propionate + HCl
-
-
-
-
?
2,3-dibromopropionate + H2O
?
2,3-dichloropropionate + H2O
?
2,3-dichloropropionic acid + H2O
3-chlorlactic acid + HCl
2-bromoacetic acid + H2O
2-hydroxyacetate + bromide
-
-
-
?
2-bromohexadecanoate + H2O
D-2-hydroxyhexadecanoate + HBr
-
-
-
-
?
2-bromopropionic acid + H2O
?
2-chloro-3-hydroxypropionate + H2O
glycerate + HCl
2-chloro-n-butyrate + H2O
2-hydroxybutyrate + HCl
2-chloroacetic acid + H2O
2-hydroxyacetate + chloride
-
-
-
?
2-chloroacrylate + H2O
2-hydroxyacrylate + HCl
-
-
-
-
?
2-chlorobutyrate + H2O
2-hydroxybutyrate + chloride
Stutzerimonas chloritidismutans
-
low activity
-
-
?
2-chloropropionate + H2O
2-hydroxypropionate + chloride
2-chloropropionate + H2O
lactate + HCl
2-chloropropionic acid + H2O
?
2-monobromobutyrate + H2O
?
-
-
-
?
2-monochlorobutyrate + H2O
?
alpha-bromophenylacetic acid + H2O
?
-
-
-
-
?
bromoacetate + H2O
hydroxyacetate + bromide
Stutzerimonas chloritidismutans
-
highest activity
-
-
?
chloroacetate + H2O
hydroxyacetate + chloride
Stutzerimonas chloritidismutans
-
high activity
-
-
?
D-2-bromopropionate + H2O
L-2-hydroxypropionate + bromide
D-2-chloropropionate + H2O
L-2-hydroxypropionate + chloride
dichloroacetic acid + H2O
?
DL-2-bromo-n-butyrate + H2O
?
DL-2-bromobutyrate + H2O
?
DL-2-bromopropionate + H2O
?
-
-
-
-
?
DL-2-bromopropionic acid + H2O
?
-
-
-
-
?
DL-2-chlorobutyrate + H2O
?
-
-
-
-
?
DL-2-chloropropionate + H2O
?
DL-2-chloropropionate + H2O
DL-2-hydroxypropionate + chloride
Stutzerimonas chloritidismutans
-
high activity
-
-
?
DL-2-haloalkanoic acid + H2O
L-2-hydroxyalkanoic acid + D-2-hydroxyalkanoic acid + halide
iodoacetic acid + H2O
acetic acid + iodide + H+
L-2-bromobutanoate + H2O
2-hydroxybutanoate + HBr
L-2-bromohexanoate + H2O
2-hydroxyhexanoate + HBr
L-2-bromopropionate + H2O
D-2-hydroxypropionate + bromide
Stutzerimonas chloritidismutans
-
high activity
-
-
?
L-2-bromopropionate + H2O
lactate + HBr
L-2-chloropropionate + H2O
?
-
-
-
-
?
L-2-chloropropionate + H2O
D-2-hydroxypropionate + chloride
L-2-chloropropionate + H2O
D-lactate + HCl
L-2-chloropropionate + H2O
lactate + HCl
L-2-chloropropionic acid + H2O
D-2-hydroxypropionate + HCl
-
-
-
-
?
L-2-chloropropionic acid + H2O
D-2-hydroxypropionic acid + HCl
L-2-haloacid + H2O
D-2-hydroxyacid + halide
L-2-haloalkanoic acid + H2O
D-2-hydroxyalkanoic acid + halide
L-2-monochloropropionate + H2O
D-2-hydroxypropionate + HCl
monobromoacetate + H2O
glycolate + HBr
monobromoacetate + H2O
hydroxyacetate + bromide
-
-
-
-
?
monobromoacetic acid + H2O
acetic acid + bromide
monochloroacetate + H2O
glycolate + HCl
monochloroacetate + H2O
hydroxyacetate + chloride
-
-
-
-
?
monoiodoacetate + H2O
glycolate + HI
monoiodoacetate + H2O
hydroxyacetate + iodide
-
-
-
-
?
additional information
?
-
(R,S)-2-chloropropionic acid + H2O
(S)-lactic acid + (S)-2-chloropropionic acid + HCl
-
-
-
-
?
(R,S)-2-chloropropionic acid + H2O
(S)-lactic acid + (S)-2-chloropropionic acid + HCl
-
-
-
-
?
(R,S)-2-chloropropionic acid + H2O
(S)-lactic acid + (S)-2-chloropropionic acid + HCl
-
-
-
-
?
(S)-2-bromopropionic acid + H2O
(R)-2-hydroxypropionic acid + bromide
-
-
-
-
?
(S)-2-bromopropionic acid + H2O
(R)-2-hydroxypropionic acid + bromide
-
41% activity compared to monobromoacetic acid
-
-
?
(S)-2-bromopropionic acid + H2O
(R)-2-hydroxypropionic acid + bromide
-
41% activity compared to monobromoacetic acid
-
-
?
(S)-2-chlorobutyric acid + H2O
(R)-2-hydroxybutyric acid + chloride
-
below 10% activity compared to monobromoacetic acid
-
-
?
(S)-2-chlorobutyric acid + H2O
(R)-2-hydroxybutyric acid + chloride
-
below 10% activity compared to monobromoacetic acid
-
-
?
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionate + chloride
-
-
-
?
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionate + chloride
the wild-type enzyme shows no activity with the (R)-enantiomer
-
-
?
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionic acid + chloride
-
-
-
?
(S)-2-chloropropionate + H2O
(R)-2-hydroxypropionic acid + chloride
the enzyme acts exclusively on (S)-isomers
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
-
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
high activity
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
enantioselective
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
14% activity compared to monobromoacetic acid
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
14% activity compared to monobromoacetic acid
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
-
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
the substrate interacts strongly with Asp10, Arg41, Lys151, and Asp180
-
-
?
(S)-2-chloropropionic acid + H2O
(R)-2-hydroxypropionic acid + chloride
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
reaction by inversion of the configuration in a mixture of dimethylsulfoxide and buffer, but in presence of stoichiometric amounts of water proceeds without inversion of the configuration contrary to the behavior in an aqueous environment
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
reaction by inversion of the configuration in a mixture of dimethylsulfoxide and buffer, but in presence of stoichiometric amounts of water proceeds without inversion of the configuration contrary to the behavior in an aqueous environment
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
648275, 648277, 648282, 648289, 648291, 648293, 648295, 648298, 648301, 648313, 648329 -
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
enzyme of 2-chloropropionate grown cells
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
substrate specificity towards chlorinated and bromated substrates is limited to short chain monosubstituated 2-halocarboxylic acids, fluoro compounds are not converted
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
substrate specificity towards chlorinated and bromated substrates is limited to short chain monosubstituated 2-halocarboxylic acids, fluoro compounds are not converted
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
?
(S)-2-haloacid + H2O
(R)-2-hydroxyacid + halide
-
-
-
-
?
1,2-dichloroethane + H2O
?
-
-
-
-
?
1,2-dichloroethane + H2O
?
-
-
-
-
?
2,2-dichloropropionate + H2O
propionate + HCl
-
53% of the activity compared to monochloroacetate
-
-
?
2,2-dichloropropionate + H2O
propionate + HCl
-
53% of the activity compared to monochloroacetate
-
-
?
2,2-dichloropropionate + H2O
propionate + HCl
-
-
-
-
?
2,3-dibromopropionate + H2O
?
-
-
-
?
2,3-dibromopropionate + H2O
?
-
-
-
-
?
2,3-dibromopropionate + H2O
?
-
-
-
?
2,3-dibromopropionate + H2O
?
-
-
-
-
?
2,3-dichloropropionate + H2O
?
-
-
-
?
2,3-dichloropropionate + H2O
?
-
-
-
?
2,3-dichloropropionic acid + H2O
3-chlorlactic acid + HCl
-
-
-
?
2,3-dichloropropionic acid + H2O
3-chlorlactic acid + HCl
-
-
-
?
2-bromopropionic acid + H2O
?
-
-
-
-
?
2-bromopropionic acid + H2O
?
-
-
-
-
?
2-bromopropionic acid + H2O
?
-
-
-
-
?
2-chloro-3-hydroxypropionate + H2O
glycerate + HCl
-
-
-
-
?
2-chloro-3-hydroxypropionate + H2O
glycerate + HCl
-
-
-
-
?
2-chloro-n-butyrate + H2O
2-hydroxybutyrate + HCl
-
-
-
-
?
2-chloro-n-butyrate + H2O
2-hydroxybutyrate + HCl
-
-
-
-
?
2-chloropropionate + H2O
2-hydroxypropionate + chloride
-
-
-
-
?
2-chloropropionate + H2O
2-hydroxypropionate + chloride
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionate + H2O
lactate + HCl
-
-
-
-
?
2-chloropropionic acid + H2O
?
-
-
-
-
?
2-chloropropionic acid + H2O
?
-
-
-
-
?
2-monochlorobutyrate + H2O
?
-
-
-
?
2-monochlorobutyrate + H2O
?
-
-
-
?
D-2-bromopropionate + H2O
L-2-hydroxypropionate + bromide
Stutzerimonas chloritidismutans
-
high activity
-
-
?
D-2-bromopropionate + H2O
L-2-hydroxypropionate + bromide
Stutzerimonas chloritidismutans AW-1T
-
high activity
-
-
?
D-2-chloropropionate + H2O
L-2-hydroxypropionate + chloride
Stutzerimonas chloritidismutans
-
very low activity
-
-
?
D-2-chloropropionate + H2O
L-2-hydroxypropionate + chloride
Stutzerimonas chloritidismutans AW-1T
-
very low activity
-
-
?
dichloroacetate + H2O
?
-
-
-
-
?
dichloroacetate + H2O
?
-
-
-
-
?
dichloroacetate + H2O
?
-
-
-
-
?
dichloroacetate + H2O
?
-
-
-
-
?
dichloroacetate + H2O
?
-
-
-
?
dichloroacetic acid + H2O
?
-
-
-
-
?
dichloroacetic acid + H2O
?
-
-
-
-
?
dichloroacetic acid + H2O
?
-
below 10% activity compared to monobromoacetic acid
-
-
?
dichloroacetic acid + H2O
?
-
below 10% activity compared to monobromoacetic acid
-
-
?
dichloroacetic acid + H2O
?
-
-
-
-
?
dichloroacetic acid + H2O
?
low activity
-
-
?
DL-2-bromo-n-butyrate + H2O
?
-
-
-
-
?
DL-2-bromo-n-butyrate + H2O
?
-
-
-
-
?
DL-2-bromo-n-butyrate + H2O
?
-
-
-
-
?
DL-2-bromobutyrate + H2O
?
-
-
-
-
?
DL-2-bromobutyrate + H2O
?
-
-
-
-
?
DL-2-chloropropionate + H2O
?
-
-
-
-
?
DL-2-chloropropionate + H2O
?
-
-
-
-
?
DL-2-chloropropionate + H2O
?
-
-
-
-
?
DL-2-haloalkanoic acid + H2O
L-2-hydroxyalkanoic acid + D-2-hydroxyalkanoic acid + halide
-
-
-
-
?
DL-2-haloalkanoic acid + H2O
L-2-hydroxyalkanoic acid + D-2-hydroxyalkanoic acid + halide
-
-
-
-
?
fatty acids + H2O
?
-
monohaloacids, short chain length C2 to C4
-
-
?
3.8.1.2 (S)-2-haloacid dehalogenase
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