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Literature summary for 1.1.1.269 extracted from

  • Sliwa, D.A.; Krishnakumar, A.M.; Peters, J.W.; Ensign, S.A.
    Molecular basis for enantioselectivity in the (R)- and (S)-hydroxypropylthioethanesulfonate dehydrogenases, a unique pair of stereoselective short-chain dehydrogenases/reductases involved in aliphatic epoxide carboxylation (2010), Biochemistry, 49, 3487-3498.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.1.1.269

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Xanthobacter autotrophicus

Protein Variants

Protein Variants Comment Organism
K160A inactive Xanthobacter autotrophicus
K214A substantially reduced catalytic efficiencies with the natural substrates in both the oxidative and reductive direction Xanthobacter autotrophicus
R211A substantially reduced catalytic efficiencies with the natural substrates in both the oxidative and reductive direction Xanthobacter autotrophicus
S143A residue acts as H-bond donor to substrate and in charge stabilization of the transition state, large increase in Km value Xanthobacter autotrophicus
Y156A mutation in general acid/base, large increase in Km value Xanthobacter autotrophicus
Y156F inactive Xanthobacter autotrophicus

Inhibitors

Inhibitors Comment Organism Structure
2-(2-methyl-2-hydroxypropylthio)ethanesulfonate competitive; competitive Xanthobacter autotrophicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.031
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.068
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.096
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.22
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.27
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.97
-
 2-(2-hydroxyethylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.6
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.8
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
2.3
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
9.1
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
9.5
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
11
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
12
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
28
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
68
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
72
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
120
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
180
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
720
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
950
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1400
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus

Organism

Organism UniProt Comment Textmining
Xanthobacter autotrophicus
-
-
-
Xanthobacter autotrophicus Q56841
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme Xanthobacter autotrophicus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
(S)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
2-(2-hydroxyethylthio)ethanesulfonate + NAD+ achiral mimic of both R-hydroxypropyl-CoM and S-hydroxypropyl-CoM, substrate for both the R- and S-HPCDH enzymes with identical Km values Xanthobacter autotrophicus 2-(formylmethylthio)ethanesulfonate + NADH + H+
-
 r
2-(R)-hydroxypropyl-CoM + NAD+
-
 Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
2-(R)-hydroxypropyl-CoM + NAD+ poor substrate. S-HPCDH3 cannot bind hydroxypropyl-CoM with CoM oriented properly in the sulfonate-binding pocket that consists of residues R211 and K214. R-hydroxypropyl-CoM binds to S-HPCDH3 with a 290-fold lower affinity but in an orientation where the hydroxyl and hydrogen on C2 can be more properly aligned with tyrosine 156 and NAD+, such that kcat decreases by 4.5-fold relative to the natural substrate S-hydroxypropyl-CoM Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
2-(S)-hydroxypropyl-CoM + NAD+
-
 Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
2-(S)-hydroxypropyl-CoM + NAD+ oxidation of S-hydroxypropyl-CoM with a kcat that is 402 times less than that for R-hydroxypropyl-CoM Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
2-butanone + NADH + H+
-
 Xanthobacter autotrophicus (S)-2-butanol + (R)-2-butanol + NAD+
-
 r
2-butanone + NADH + H+
-
 Xanthobacter autotrophicus (S)-2-butanol + (R)-2-butanol + NAD+ without additions, 99.2% (S)-enantiomer + 0.8% (R)-enantiomer, in presence of 1 mM ethansulfonate 99.0% (S)-enantiomer + 2% (R)-enantiomer. Mutant K214A, without additions, 91.6% (S)-enantiomer + 8.4% (R)-enantiomer, in presence of 1 mM ethansulfonate 90.9% (S)-enantiomer + 9.1% (R)-enantiomer r
2-oxopropyl-CoM + NADH + H+
-
 Xanthobacter autotrophicus 2-(R)-hydroxypropyl-CoM + NAD+
-
 r
2-propanol + NAD+
-
 Xanthobacter autotrophicus acetone + NADH + H+
-
 r

Synonyms

Synonyms Comment Organism
HPCDH3
-
 Xanthobacter autotrophicus
xecE1
-
 Xanthobacter autotrophicus
xecE3
-
 Xanthobacter autotrophicus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.013
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
0.039
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
0.044
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.072
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
0.12
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.65
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
1
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.7
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.7
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
2
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
2.6
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
3.8
-
 2-(2-hydroxyethylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
5.5
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
5.8
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
8.6
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
9.6
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
11
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
16
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
25
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
29
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
49
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.29
-
 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
0.29
-
 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0014
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
0.0148
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.0928
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.35
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
0.37
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.4
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
0.53
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.54
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
0.6
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
0.75
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
0.81
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.4
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.8
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
2.4
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
2.5
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
10
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
39
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
420
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
500
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
790
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus