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Literature summary for 1.1.1.268 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)

Cloned (Comment) Organism
expression in Escherichia coli Xanthobacter autotrophicus

Inhibitors

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

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
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
0.96
-
2-(2-hydroxyethylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
220
-
(R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
350
-
(S)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus

Organism

Organism UniProt Comment Textmining
Xanthobacter autotrophicus Q56840
-
-

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-(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+ without additions, 71.9% (S)-enantiomer + 28% (R)-enantiomer, in presence of 1 mM ethansulfonate 92.7% (S)-enantiomer + 7.3% (R)-enantiomer r
2-oxopropyl-CoM + NADH + H+
-
Xanthobacter autotrophicus 2-(R)-hydroxypropyl-CoM + NAD+
-
r
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 ?
-
?

Synonyms

Synonyms Comment Organism
xecD
-
Xanthobacter autotrophicus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.12
-
2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
0.55
-
2-(2-hydroxyethylthio)ethanesulfonate pH 7.5, 30°C Xanthobacter autotrophicus
1.9
-
(R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
9.3
-
(S)-2-butanol 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

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.53
-
2-(S)-hydroxypropyl-CoM pH 7.5, 30°C Xanthobacter autotrophicus
8.69
-
(R)-2-butanol pH 7.5, 30°C Xanthobacter autotrophicus
26.4
-
(S)-2-butanol 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