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Literature summary 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

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.268 expression in Escherichia coli Xanthobacter autotrophicus
1.1.1.269 expression in Escherichia coli Xanthobacter autotrophicus

Protein Variants

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.268 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate competitive Xanthobacter autotrophicus
1.1.1.269 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate competitive; competitive Xanthobacter autotrophicus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.268 0.068
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 0.096
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 0.22
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 0.96
-
 2-(2-hydroxyethylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 220
-
 (R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 350
-
 (S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.031
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.068
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.096
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.22
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.27
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.97
-
 2-(2-hydroxyethylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.6
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.8
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 2.3
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 9.1
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 9.5
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 11
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 12
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 28
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 68
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 72
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 120
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 180
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 720
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 950
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1400
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.268 Xanthobacter autotrophicus Q56840
-
-
1.1.1.269 Xanthobacter autotrophicus
-
-
-
1.1.1.269 Xanthobacter autotrophicus Q56841
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.268 recombinant enzyme Xanthobacter autotrophicus
1.1.1.269 recombinant enzyme Xanthobacter autotrophicus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.268 (R)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
1.1.1.268 (S)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
1.1.1.268 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
1.1.1.268 2-(R)-hydroxypropyl-CoM + NAD+
-
 Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
1.1.1.268 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
1.1.1.268 2-butanone + NADH + H+
-
 Xanthobacter autotrophicus (S)-2-butanol + (R)-2-butanol + NAD+ without additions, 71.9% (S)-enantiomer + 28% (R)-enantiomer, in presence of 1 mM ethansulfonate 92.7% (S)-enantiomer + 7.3% (R)-enantiomer r
1.1.1.268 2-oxopropyl-CoM + NADH + H+
-
 Xanthobacter autotrophicus 2-(R)-hydroxypropyl-CoM + NAD+
-
 r
1.1.1.268 additional information R-HPCDH1 can bind either enantiomer of hydroxypropyl-CoM with the CoM moiety oriented properly in the sulfonate-binding pocket consisting of R152 and R196. A high-affinity ternary complex of S-HPC, NAD+ forms, but the misalignment of the hydrogen and hydroxyl groups on C2 relative to NAD+ and the tyrosine general base results in a 403-fold lower turnover rate for the S-enantiomer Xanthobacter autotrophicus ?
-
 ?
1.1.1.269 (R)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
1.1.1.269 (S)-2-butanol + NAD+
-
 Xanthobacter autotrophicus 2-butanone + NADH + H+
-
 r
1.1.1.269 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
1.1.1.269 2-(R)-hydroxypropyl-CoM + NAD+
-
 Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
1.1.1.269 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
1.1.1.269 2-(S)-hydroxypropyl-CoM + NAD+
-
 Xanthobacter autotrophicus 2-oxopropyl-CoM + NADH + H+
-
 r
1.1.1.269 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
1.1.1.269 2-butanone + NADH + H+
-
 Xanthobacter autotrophicus (S)-2-butanol + (R)-2-butanol + NAD+
-
 r
1.1.1.269 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
1.1.1.269 2-oxopropyl-CoM + NADH + H+
-
 Xanthobacter autotrophicus 2-(R)-hydroxypropyl-CoM + NAD+
-
 r
1.1.1.269 2-propanol + NAD+
-
 Xanthobacter autotrophicus acetone + NADH + H+
-
 r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.268 xecD
-
 Xanthobacter autotrophicus
1.1.1.269 HPCDH3
-
 Xanthobacter autotrophicus
1.1.1.269 xecE1
-
 Xanthobacter autotrophicus
1.1.1.269 xecE3
-
 Xanthobacter autotrophicus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.268 0.12
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 0.55
-
 2-(2-hydroxyethylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 1.9
-
 (R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 9.3
-
 (S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 29
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 49
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.013
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.039
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.044
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.072
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.12
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.65
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.7
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.7
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 2
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 2.6
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 3.8
-
 2-(2-hydroxyethylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 5.5
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 5.8
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 8.6
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 9.6
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 11
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 16
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 25
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 29
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 49
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.1.1.268 0.29
-
 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.29
-
 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.29
-
 2-(2-methyl-2-hydroxypropylthio)ethanesulfonate wild-type, pH 7.5, 30°C Xanthobacter autotrophicus

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.268 0.53
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 8.69
-
 (R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 26.4
-
 (S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 420
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.268 500
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.0014
-
 2-(S)-hydroxypropyl-CoM mutant S143A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.0148
-
 (R)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.0928
-
 (S)-2-butanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.35
-
 2-(S)-hydroxypropyl-CoM mutant Y156A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.37
-
 2-butanone wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.4
-
 2-butanone mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.53
-
 2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.54
-
 2-butanone mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.6
-
 2-(R)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.75
-
 2-oxopropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 0.81
-
 2-oxopropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.4
-
 2-propanol wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 1.8
-
 2-propanol mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 2.4
-
 2-propanol mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 2.5
-
 2-(S)-hydroxypropyl-CoM mutant K214A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 10
-
 2-(S)-hydroxypropyl-CoM mutant R211A, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 39
-
 2-oxopropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 420
-
 2-oxopropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 500
-
 2-(R)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
1.1.1.269 790
-
 2-(S)-hydroxypropyl-CoM wild-type, pH 7.5, 30°C Xanthobacter autotrophicus