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Literature summary for 1.1.1.268 extracted from

  • Clark, D.D.; Boyd, J.M.; Ensign, S.A.
    The stereoselectivity and catalytic properties of Xanthobacter autotrophicus 2-[(R)-2-hydroxypropylthio]ethanesulfonate dehydrogenase are controlled by interactions between C-terminal arginine residues and the sulfonate of coenzyme M (2004), Biochemistry, 43, 6763-6771.
    View publication on PubMed

Activating Compound

Activating Compound Comment Organism Structure
ethanesulfonate 1 mM, 5.6fold increase in ratio of turnover number to Km-value for 2-butanone as substrate Xanthobacter autotrophicus
methanesulfonate 1 mM, 5.6fold increase in ratio of turnover number to Km-value for 2-butanone as substrate Xanthobacter autotrophicus
propanesulfonate 1 mM, 1.7fold increase in ratio of turnover number to Km-value for 2-butanone as substrate Xanthobacter autotrophicus

Cloned(Commentary)

Cloned (Comment) Organism
-
Xanthobacter autotrophicus

Protein Variants

Protein Variants Comment Organism
R152A the ratio of turnover number to Km-value for 2-(2-ketopropylthio)ethanesulfonate is 5192fold lower than the ratio for the wild-type enzyme. The ratio of turnover number to Km-value for 2-butanone is 1.3fold higher than the ratio for the wild-type enzyme Xanthobacter autotrophicus
R179A no detectable activity with 2-(2-ketopropylthio)ethanesulfonate and 2-butanone Xanthobacter autotrophicus
R196A the ratio of turnover number to Km-value for 2-(2-ketopropylthio)ethanesulfonate is 1000fold lower than the ratio for the wild-type enzyme. The ratio of turnover number to Km-value for 2-butanone is 2.7fold higher than the ratio for the wild-type enzyme Xanthobacter autotrophicus
R203A the ratio of turnover number to Km-value for 2-(2-ketopropylthio)ethanesulfonate is 4.3fold lower than the ratio for the wild-type enzyme. The ratio of turnover number to Km-value for 2-butanone is 1.6fold lower than the ratio for the wild-type enzyme Xanthobacter autotrophicus
R209A the ratio of turnover number to Km-value for 2-(2-ketopropylthio)ethanesulfonate is 2.7fold lower than the ratio for the wild-type enzyme. The ratio of turnover number to Km-value for 2-butanone is 1.4fold lower than the ratio for the wild-type enzyme Xanthobacter autotrophicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.092
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, wild-type enzyme Xanthobacter autotrophicus
0.1
-
2-[(S)-2-hydroxypropylthio]ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
0.102
-
2-[(R)-2-hydroxypropylthio]ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
0.44
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, mutant enzyme R209A Xanthobacter autotrophicus
1.08
-
(R)-2-octanol pH 7.5, 30°C Xanthobacter autotrophicus
2 3 2-butanone pH 7.5, 30°C, mutant enzyme R196A Xanthobacter autotrophicus
2.64
-
(R)-2-heptanol pH 7.5, 30°C Xanthobacter autotrophicus
4.6
-
(R)-2-hexanol pH 7.5, 30°C Xanthobacter autotrophicus
20
-
(R)-2-pentanol pH 7.5, 30°C Xanthobacter autotrophicus
39
-
2-butanone pH 7.5, 30°C, mutant enzyme R203A Xanthobacter autotrophicus
41
-
2-butanone pH 7.5, 30°C, mutant enzyme R152A Xanthobacter autotrophicus
52
-
2-butanone pH 7.5, 30°C, wild-type enzyme Xanthobacter autotrophicus
84
-
2-butanone pH 7.5, 30°C, mutant enzyme R209A Xanthobacter autotrophicus
153
-
(S)-2-pentanol pH 7.5, 30°C Xanthobacter autotrophicus
315
-
(S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
328
-
(R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1726
-
2-propanol pH 7.5, 30°C Xanthobacter autotrophicus

Organism

Organism UniProt Comment Textmining
Xanthobacter autotrophicus
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-2-butanol + NAD+ the enantiomeric selectivity of the reverse reaction is 39.6% for (S)-2-butanol without additive, 90.8% with 1 mM CH3CH2SO3-Na+ as additive, 87.8% with 1 mM HSCH2CH2SO3-Na+ as additive, 52.0% with 1 mM CH3CH2COO-Na+ as additive, 46.6% with 1 mM CH3COO-Na+ as additive, 44.8% with 1 mM CH3CH2NH3+Cl- as additive, 45.4% with 1 mM CH3CH2OH as additive, 45.8% with 1 mM Na2SO4 as additive and 40.4% with 1 mM NaCl as additive Xanthobacter autotrophicus 2-butanone + NADH + H+
-
r
(R)-2-heptanol + NAD+
-
Xanthobacter autotrophicus 2-heptanone + NADH + H+
-
?
(R)-2-hexanol + NAD+
-
Xanthobacter autotrophicus 2-hexanone + NADH + H+
-
?
(R)-2-octanol + NAD+
-
Xanthobacter autotrophicus 2-octanone + NADH + H+
-
?
(R)-2-pentanol + NAD+
-
Xanthobacter autotrophicus 2-pentanone + NADH + H+
-
?
(S)-2-butanol + NAD+
-
Xanthobacter autotrophicus 2-butanone + NADH + H+
-
?
(S)-2-pentanol + NAD+
-
Xanthobacter autotrophicus 2-pentanone + NADH + H+
-
?
2-propanol + NAD+
-
Xanthobacter autotrophicus acetone + NADH + H+
-
?
2-[(R)-2-hydroxypropylthio]ethanesulfonate + NAD+ the enzyme is highly specific for the R-enantiomer Xanthobacter autotrophicus 2-(2-ketopropylthio)ethanesulfonate + NADH + H+
-
r
2-[(S)-2-hydroxypropylthio]ethanesulfonate + NAD+ the enzyme is highly specific for the R-enantiomer Xanthobacter autotrophicus 2-(2-ketopropylthio)ethanesulfonate + NADH + H+
-
r

Synonyms

Synonyms Comment Organism
R-HPCDH
-
Xanthobacter autotrophicus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.012
-
2-butanone pH 7.5, 30°C, mutant enzyme R203A Xanthobacter autotrophicus
0.027
-
2-butanone pH 7.5, 30°C, wild-type enzyme Xanthobacter autotrophicus
0.028
-
2-butanone pH 7.5, 30°C, mutant enzyme R152A Xanthobacter autotrophicus
0.032
-
2-butanone pH 7.5, 30°C, mutant enzyme R209A Xanthobacter autotrophicus
0.033
-
2-butanone pH 7.5, 30°C, mutant enzyme R196A Xanthobacter autotrophicus
0.044
-
2-[(S)-2-hydroxypropylthio]ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
0.98
-
(R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1
-
(R)-2-pentanol pH 7.5, 30°C Xanthobacter autotrophicus
1.4
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, mutant enzyme R152A Xanthobacter autotrophicus
1.7
-
(R)-2-octanol pH 7.5, 30°C Xanthobacter autotrophicus
1.8
-
(R)-2-heptanol pH 7.5, 30°C Xanthobacter autotrophicus
2.2
-
(S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
2.4
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, mutant enzyme R196A Xanthobacter autotrophicus
2.7
-
(R)-2-hexanol pH 7.5, 30°C Xanthobacter autotrophicus
2.9
-
2-propanol pH 7.5, 30°C Xanthobacter autotrophicus
2.9
-
(S)-2-pentanol pH 7.5, 30°C Xanthobacter autotrophicus
15
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, mutant enzyme R209A Xanthobacter autotrophicus
24.5
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, wild-type enzyme Xanthobacter autotrophicus
26.8
-
2-[(R)-2-hydroxypropylthio]ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
27.9
-
2-(2-ketopropylthio)ethanesulfonate pH 7.5, 30°C, mutant enzyme R203A Xanthobacter autotrophicus