1.1.1.268: 2-(R)-hydroxypropyl-CoM dehydrogenase
This is an abbreviated version!
For detailed information about 2-(R)-hydroxypropyl-CoM dehydrogenase, go to the full flat file.
Reaction
Synonyms
(R)-hydroxypropyl-coenzyme M dehydrogenase, (R)-hydroxypropylthioethanesulfonate dehydrogenase, 2-(2-(R)-hydroxypropylthio)ethanesulfonate dehydrogenase, 2-(R)-hydroxypropyl-coenzyme M dehydrogenase, R-HPCDH, xecD
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Substrates Products
Substrates Products on EC 1.1.1.268 - 2-(R)-hydroxypropyl-CoM dehydrogenase
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REACTION DIAGRAM
(2S)-2-butanol + NAD+
2-butanone + NADH + H+
very low activity
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r
2-(2-hydroxyethylthio)ethanesulfonate + NAD+
2-(formylmethylthio)ethanesulfonate + NADH + H+
achiral mimic of both R-hydroxypropyl-CoM and S-hydroxypropyl-CoM, substrate for both the R- and S-HPCDH enzymes with identical Km values
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r
2-(2-hydroxyethylthio)ethanesulfonate + NADH + H+
?
very low activity
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?
2-(S)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
oxidation of S-hydroxypropyl-CoM with a kcat that is 402 times less than that for R-hydroxypropyl-CoM
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r
2-butanone + NADH + H+
(2R)-2-butanol + NAD+
with no additives present, all forms of recombinant R-HPCDH prefer a re-face hydride addition to produce an enantiomeric excess (EE) of (S)-2-butanol, S- and R-2-butanol are comparably good substrates for the reverse reaction. The sulfonate of ethanesulfonate interacts with R152 and R196 in the CoM binding pocket alongside 2-butanone, in a way that discourages a si-face hydride addition to produce (R)-2-butanol
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r
2-butanone + NADH + H+
(2S)-2-butanol + NAD+
with no additives present, all forms of recombinant R-HPCDH prefer a re-face hydride addition to produce an enantiomeric excess (EE) of (S)-2-butanol, S- and R-2-butanol are comparably good substrates for the reverse reaction. The sulfonate of ethanesulfonate interacts with R152 and R196 in the CoM binding pocket alongside 2-butanone, in a way that discourages a si-face hydride addition to produce (R)-2-butanol
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r
2-butanone + NADH + H+
(S)-2-butanol + (R)-2-butanol + NAD+
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without additions, 71.9% (S)-enantiomer + 28% (R)-enantiomer, in presence of 1 mM ethansulfonate 92.7% (S)-enantiomer + 7.3% (R)-enantiomer
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r
2-oxopropyl-CoM + NADH + H+
2-(R)-hydroxypropyl-CoM + NAD+
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r
2-[(R)-2-hydroxypropylthio]ethanesulfonate + NAD+
2-(2-ketopropylthio)ethanesulfonate + NADH + H+
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the enzyme is highly specific for the R-enantiomer
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r
2-[(S)-2-hydroxypropylthio]ethanesulfonate + NAD+
2-(2-ketopropylthio)ethanesulfonate + NADH + H+
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the enzyme is highly specific for the R-enantiomer
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r
2-oxopropyl-CoM + NADH + H+
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r
(2R)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
substrate binding structure, overview
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r
(2R)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
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-
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r
(2R)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
substrate binding structure, overview
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-
r
2-oxopropyl-CoM + NADH + H+
competitive inhibitor to the R-enantiomer of substrate, very low activity
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r
(2S)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
competitive inhibitor to the R-enantiomer of substrate, very low activity
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r
(R)-2-butanol + NAD+
2-butanone + NADH + H+
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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
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r
2-(2-oxoethylthio)ethanesulfonate + NADH
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-
?
2-(2-hydroxyethylthio)ethanesulfonate + NAD+
2-(2-oxoethylthio)ethanesulfonate + NADH
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?
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH
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bacterial propylene metabolism
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?
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH
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bacterial propylene metabolism
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?
2-oxopropyl-CoM + NADH + H+
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?
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
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-
?
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
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r
2-propanol + NAD+
2-propanone + NADH + H+
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r
?
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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
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?
additional information
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substrate specificity of the stereochemically different isozymes, R- and S-HPCDH (EC 1.1.1.269) are 41% identical to each other, overview. No activity with (S)-2-hexanol, (S)-2-heptanol, and (S)-2-octanol. Stereochemistry of products from reaction with wild-type and mutant enzymes with or without addition of additives, i.e. CH3CH2SO3- Na+, HSCH2CH2SO3- Na+, CH3CH2COO- Na+, CH3COO- Na+, CH3CH2NH3 +Cl-, CH3CH2OH, Na2SO4, and NaCl, overview
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additional information
?
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substrate specificity of the stereochemically different isozymes, R- and S-HPCDH (EC 1.1.1.269) are 41% identical to each other, overview. No activity with (S)-2-hexanol, (S)-2-heptanol, and (S)-2-octanol. Stereochemistry of products from reaction with wild-type and mutant enzymes with or without addition of additives, i.e. CH3CH2SO3- Na+, HSCH2CH2SO3- Na+, CH3CH2COO- Na+, CH3COO- Na+, CH3CH2NH3 +Cl-, CH3CH2OH, Na2SO4, and NaCl, overview
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