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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

2-(R)-hydroxypropyl-CoM
+
NAD+
=
2-oxopropyl-CoM
+
NADH
+
H+

Synonyms

(R)-hydroxypropyl-coenzyme M dehydrogenase, (R)-hydroxypropylthioethanesulfonate dehydrogenase, 2-(2-(R)-hydroxypropylthio)ethanesulfonate dehydrogenase, 2-(R)-hydroxypropyl-coenzyme M dehydrogenase, R-HPCDH, xecD

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.268 2-(R)-hydroxypropyl-CoM dehydrogenase

Substrates Products

Substrates Products on EC 1.1.1.268 - 2-(R)-hydroxypropyl-CoM dehydrogenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
-
-
-
r
(2R)-2-heptanol + NAD+
2-heptanone + NADH + H+
show the reaction diagram
-
-
-
r
(2R)-2-hexanol + NAD+
2-hexanone + NADH + H+
show the reaction diagram
-
-
-
r
(2R)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
show the reaction diagram
(2R)-2-octanol + NAD+
2-octanone + NADH + H+
show the reaction diagram
-
-
-
r
(2R)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
-
-
-
r
(2S)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
very low activity
-
-
r
(2S)-2-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
show the reaction diagram
(2S)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
-
-
-
r
(R)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
(R)-2-heptanol + NAD+
2-heptanone + NADH + H+
show the reaction diagram
-
-
-
-
?
(R)-2-hexanol + NAD+
2-hexanone + NADH + H+
show the reaction diagram
-
-
-
-
?
(R)-2-octanol + NAD+
2-octanone + NADH + H+
show the reaction diagram
-
-
-
-
?
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
-
-
-
-
?
(S)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
-
-
-
-
?
2-(2-hydroxyethylthio)ethanesulfonate + NAD+
2-(2-oxoethylthio)ethanesulfonate + NADH
show the reaction diagram
2-(2-hydroxyethylthio)ethanesulfonate + NAD+
2-(formylmethylthio)ethanesulfonate + NADH + H+
show the reaction diagram
achiral mimic of both R-hydroxypropyl-CoM and S-hydroxypropyl-CoM, substrate for both the R- and S-HPCDH enzymes with identical Km values
-
-
r
2-(2-hydroxyethylthio)ethanesulfonate + NADH + H+
?
show the reaction diagram
very low activity
-
-
?
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH
show the reaction diagram
2-(R)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
show the reaction diagram
2-(S)-hydroxypropyl-CoM + NAD+
2-oxopropyl-CoM + NADH + H+
show the reaction diagram
oxidation of S-hydroxypropyl-CoM with a kcat that is 402 times less than that for R-hydroxypropyl-CoM
-
-
r
2-butanone + NADH + H+
(2R)-2-butanol + NAD+
show the reaction diagram
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
-
-
r
2-butanone + NADH + H+
(2S)-2-butanol + NAD+
show the reaction diagram
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
-
-
r
2-butanone + NADH + H+
(S)-2-butanol + (R)-2-butanol + NAD+
show the reaction diagram
-
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+
2-(R)-hydroxypropyl-CoM + NAD+
show the reaction diagram
-
-
-
r
2-propanol + NAD+
2-propanone + NADH + H+
show the reaction diagram
2-propanol + NAD+
acetone + NADH + H+
show the reaction diagram
-
-
-
-
?
2-[(R)-2-hydroxypropylthio]ethanesulfonate + NAD+
2-(2-ketopropylthio)ethanesulfonate + NADH + H+
show the reaction diagram
-
the enzyme is highly specific for the R-enantiomer
-
-
r
2-[(S)-2-hydroxypropylthio]ethanesulfonate + NAD+
2-(2-ketopropylthio)ethanesulfonate + NADH + H+
show the reaction diagram
-
the enzyme is highly specific for the R-enantiomer
-
-
r
additional information
?
-