1.1.9.1: alcohol dehydrogenase (azurin)

This is an abbreviated version!
For detailed information about alcohol dehydrogenase (azurin), go to the full flat file.

Reaction

a primary alcohol
+
azurin
=
an aldehyde
+
reduced azurin

Synonyms

ADH IIB, ADH IIG, QH-ADH, quinohaemoprotein alcohol dehydrogenase, quinohemoprotein alcohol dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.9 With a copper protein as acceptor
                1.1.9.1 alcohol dehydrogenase (azurin)

Substrates Products

Substrates Products on EC 1.1.9.1 - alcohol dehydrogenase (azurin)

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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
(R)-2-butanol + ferricyanide
butan-2-one + ferrocyanide
show the reaction diagram
-
enzyme electrode, 6.5% of vmax with 1-butanol, soluble enzyme, 6% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 13fold preferred over (R)-enantiomer, with soluble enzyme 13.5fold, respectively
-
-
?
(R)-2-heptanol + ferricyanide
heptan-2-one + ferrocyanide
show the reaction diagram
-
enzyme electrode, 10% of vmax with 1-butanol, soluble enzyme, 5.5% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 82fold preferred over (R)-enantiomer, with soluble enzyme 315fold, respectively
-
-
?
(R)-2-hexanol + ferrocyanide
hexan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 14% of vmax with 1-butanol, soluble enzyme, 9% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 35fold preferred over (R)-enantiomer, with soluble enzyme 105fold, respectively
-
-
?
(R)-2-octanol + ferrocyanide
octan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 8% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 82fold preferred over (R)-enantiomer, with soluble enzyme 800fold, respectively
-
-
?
(R)-3-bromo-2-methyl-1-propanol + ferricyanide
(R)-3-bromo-2-methyl-propanal + ferrocyanide
show the reaction diagram
-
-
-
-
r
(R)-glycidol + ferrocyanide
? + ferricyanide
show the reaction diagram
-
enzyme electrode, 37% of vmax with 1-butanol, soluble enzyme, 1.6% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 0.9fold preferred over (R)-enantiomer, with soluble enzyme no distinction
-
-
?
(R)-solketal + 2 ferricyanide
(R)-solketal aldehyde + 2 ferrocyanide + 2 H+
show the reaction diagram
-
(R)-enantiomer is prefered, enantiomeric ratio is 30
-
-
r
(R)-solketal + ferrocyanide
? + ferricyanide
show the reaction diagram
-
enzyme electrode, 35% of vmax with 1-butanol, soluble enzyme, 10% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 39fold preferred over (R)-enantiomer, with soluble enzyme 117fold, respectively
-
-
?
(R)-solketal aldehyde + ferrocyanide
(R)-solketal + ferricyanide
show the reaction diagram
(S)-2-butanol + ferricyanide
butan-2-one + ferrocyanide
show the reaction diagram
-
enzyme electrode, 14% of vmax with 1-butanol, soluble enzyme, 13% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 13fold preferred over (R)-enantiomer, with soluble enzyme 13.5fold, respectively
-
-
?
(S)-2-heptanol + ferricyanide
heptan-2-one + ferrocyanide
show the reaction diagram
-
enzyme electrode, 70% of vmax with 1-butanol, soluble enzyme, 63% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 82fold preferred over (R)-enantiomer, with soluble enzyme 315fold, respectively
-
-
?
(S)-2-hexanol + ferrocyanide
hexan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 74% of vmax with 1-butanol, soluble enzyme, 71% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 35fold preferred over (R)-enantiomer, with soluble enzyme 105fold, respectively
-
-
?
(S)-2-octanol + ferrocyanide
octan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 82% of vmax with 1-butanol, soluble enzyme, 80% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 82fold preferred over (R)-enantiomer, with soluble enzyme 800fold, respectively
-
-
?
(S)-glycidol + ferrocyanide
? + ferricyanide
show the reaction diagram
-
enzyme electrode, 30% of vmax with 1-butanol, soluble enzyme, 1.6% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 0.9fold preferred over (R)-enantiomer, with soluble enzyme no disticnction
-
-
?
(S)-solketal + 2 ferricyanide
(S)-solketal aldehyde + 2 ferrocyanide + 2 H+
show the reaction diagram
-
the second step in (S)-solketal conversion is much faster than the first one and that opposite enantiomeric preferences exist for the alcohol and the aldehyde substrates. (R)-enantiomer is prefered, enantiomeric ratio is 30 for initial rate measurement, 117 for progress curve analysis
-
-
r
(S)-solketal + ferrocyanide
? + ferricyanide
show the reaction diagram
-
enzyme electrode, 9% of vmax with 1-butanol, 0.7% of vmax with 1-butanol. With enzyme electrode, (S)-enantiomer is 39fold preferred over (R)-enantiomer, with soluble enzyme 117fold, respectively
-
-
?
1,2-butanediol + ferricyanide
2-hydroxybutanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 84% of the activity with 1-butanol. ADH IIG, 86% of the activity with 1,2-propanediol
-
-
?
1,2-cyclohexanediol + ferricyanide
2-hydroxycyclohexanone + ferrocyanide
show the reaction diagram
-
-
-
-
?
1,2-ethanediol + ferricyanide
hydroxyacetaldehyde + ferrocyanide
show the reaction diagram
-
ADH IIB, 0% of the activity with 1-butanol. ADH IIG, 71% of the activity with 1,2-propanediol
-
-
?
1,2-propanediol + ferricyanide
2-hydroxypropanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 43% of the activity with 1-butanol. ADH IIG, maximum activity
-
-
?
1,3-butanediol + ferricyanide
3-hydroxybutanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 105% of the activity with 1-butanol. ADH IIG, 75% of the activity with 1,2-propanediol
-
-
?
1,3-butanediol + ferricyanide
? + ferrocyanide
show the reaction diagram
-
enzyme electrode, 91% of vmax with 1-butanol
-
-
?
1,3-cyclohexanediol + ferricyanide
3-hydroxycyclohexanone + ferrocyanide
show the reaction diagram
-
-
-
-
?
1,3-propandione + ferricyanide
3-hydroxypropanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 61% of the activity with 1-butanol. ADH IIG, 42% of the activity with 1,2-propanediol
-
-
?
1,4-butanediol + ferricyanide
4-hydroxybutanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 110% of the activity with 1-butanol. ADH IIG, 75% of the activity with 1,2-propanediol
-
-
?
1-butanol + ferricyanide
butanal + ferrocyanide
show the reaction diagram
1-butanol + N,N,N',N'-tetramethyl-p-phenylenediamine
butanal + ?
show the reaction diagram
-
-
-
-
r
1-heptanol + ferricyanide
heptanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 99% of the activity with 1-butanol. ADH IIG, 39% of the activity with 1,2-propanediol
-
-
?
1-hexanol + ferricyanide
hexanal + ferrocyanide
show the reaction diagram
-
ADH IIB, 70% of the activity with 1-butanol. ADH IIG, 46% of the activity with 1,2-propanediol
-
-
?
1-octanol + ferricyanide
octanal + ferrocyanide
show the reaction diagram
1-octanol + ferrocyanide
octanal + ferricyanide
show the reaction diagram
-
enzyme electrode, 95% of vmax with 1-butanol, soluble enzyme, 95% of vmax with 1-butanol
-
-
?
1-octanol + N,N,N',N'-tetramethyl-p-phenylenediamine
octanal + ?
show the reaction diagram
-
-
-
-
r
1-pentanol + ferricyanide
pentanal + ferrocyanide
show the reaction diagram
1-pentanol + ferrocyanide
pentanal + ferricyanide
show the reaction diagram
-
enzyme electrode, 93% of vmax with 1-butanol, soluble enzyme, 100% of vmax with 1-butanol
-
-
?
1-pentanol + N,N,N',N'-tetramethyl-p-phenylenediamine
pentanal + ?
show the reaction diagram
-
-
-
-
r
1-propanol + ferricyanide
propanal + ferrocyanide
show the reaction diagram
1-propanol + N,N,N',N'-tetramethyl-p-phenylenediamine
propanal + ?
show the reaction diagram
-
-
-
-
r
2,3-butanediol + ferricyanide
3-hydroxybutan-2-one + ferrocyanide
show the reaction diagram
-
ADH IIB, 12% of the activity with 1-butanol. ADH IIG, 71% of the activity with 1,2-propanediol
-
-
?
2,4-pentanediol + ferricyanide
4-hydroxypentan-2-one + ferrocyanide
show the reaction diagram
-
ADH IIB, 45% of the activity with 1-butanol. ADH IIG, 0% of the activity with 1,2-propanediol
-
-
?
2-butanol + ferricyanide
butanone + ferrocyanide
show the reaction diagram
2-butanol + ferrocyanide
butanone + ferricyanide
show the reaction diagram
-
enzyme electrode, 17% of vmax with 1-butanol, soluble enzyme, 10% of vmax with 1-butanol
-
-
?
2-hexanol + ferricyanide
hexan-2-one + ferrocyanide
show the reaction diagram
-
ADH IIB, 99% of the activity with 1-butanol. ADH IIG, 33% of the activity with 1,2-propanediol
-
-
?
2-methylcyclohexanol + ferricyanide
2-methylcyclohexanone + ferrocyanide
show the reaction diagram
-
-
-
-
?
2-octanol + ferricyanide
octan-2-one + ferrocyanide
show the reaction diagram
-
-
-
-
?
2-octanol + ferrocyanide
octan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 84% of vmax with 1-butanol, soluble enzyme, 80% of vmax with 1-butanol
-
-
?
2-pentanol + ferricyanide
pentan-2-one + ferrocyanide
show the reaction diagram
2-pentanol + ferrocyanide
pentan-2-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 40% of vmax with 1-butanol, soluble enzyme, 34% of vmax with 1-butanol
-
-
?
2-propanol + ferricyanide
acetone + ferrocyanide
show the reaction diagram
2-propanol + ferrocyanide
acetone + ferricyanide
show the reaction diagram
-
enzyme electrode, 9% of vmax with 1-butanol, soluble enzyme, 6% of vmax with 1-butanol
-
-
?
3-heptanol + ferricyanide
heptan-3-one + ferrocyanide
show the reaction diagram
-
-
-
-
?
3-heptanol + ferrocyanide
heptan-3-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 3.7% of vmax with 1-butanol, soluble enzyme, 1% of vmax with 1-butanol
-
-
?
3-hexanol + ferricyanide
hexan-3-one + ferrocyanide
show the reaction diagram
-
-
-
-
?
3-hexanol + ferrocyanide
hexan-3-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 6.5% of vmax with 1-butanol, soluble enzyme, 9% of vmax with 1-butanol
-
-
?
3-methyl-2-pentanol + ferricyanide
3-methylpentan-2-one + ferrocyanide
show the reaction diagram
3-methylcyclohexanol + ferricyanide
3-methylcyclohexanone + ferrocyanide
show the reaction diagram
-
-
-
-
?
3-nonanol + ferricyanide
nonan-3-one + ferrocyanide
show the reaction diagram
3-octanol + ferricyanide
octan-3-one + ferrocyanide
show the reaction diagram
-
-
-
-
?
3-octanol + ferrocyanide
octan-3-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 10% of vmax with 1-butanol, soluble enzyme, 10% of vmax with 1-butanol
-
-
?
3-pentanol + ferricyanide
pentan-3-one + ferrocyanide
show the reaction diagram
3-pentanol + ferrocyanide
pentan-3-one + ferricyanide
show the reaction diagram
-
enzyme electrode, 1% of vmax with 1-butanol, soluble enzyme, 1.4% of vmax with 1-butanol
-
-
?
4-decanol + ferricyanide
decan-4-one + ferrocyanide
show the reaction diagram
4-heptanol + ferricyanide
heptan-4-one + ferrocyanide
show the reaction diagram
4-methyl-2-pentanol + ferricyanide
4-methylpentan-2-one + ferrocyanide
show the reaction diagram
-
enzyme electrode, 5.6% of vmax with 1-butanol
-
-
?
6-aminohexan-1-ol + N,N,N',N'-tetramethyl-p-phenylenediamine
6-aminohexanal + ?
show the reaction diagram
-
-
-
-
r
acetaldehyde + reduced N,N,N',N'-tetramethyl-p-phenylenediamine
ethanol + N,N,N',N'-tetramethyl-p-phenylenediamine
show the reaction diagram
-
-
-
-
r
allyl alcohol + ferricyanide
prop-2-enal + ferrocyanide
show the reaction diagram
-
ADH IIB, 160% of the activity with 1-butanol. ADH IIG, 46% of the activity with 1,2-propanediol
-
-
?
benzyl alcohol + N,N,N',N'-tetramethyl-p-phenylenediamine
benzaldehyde + ?
show the reaction diagram
-
-
-
-
r
butanal + ferrocyanide
1-butanol + ferricyanide
show the reaction diagram
-
ADH IIB, 32% of the activity with 1-butanol. ADH IIG, 13% of the activity with 1,2-propanediol
-
-
?
butanal + reduced N,N,N',N'-tetramethyl-p-phenylenediamine
1-butanol + N,N,N',N'-tetramethyl-p-phenylenediamine
show the reaction diagram
-
-
-
-
r
butane-1,3-diol + N,N,N',N'-tetramethyl-p-phenylenediamine
?
show the reaction diagram
-
-
-
-
r
cyclohexanol + ferricyanide
cyclohexanal + ferrocyanide
show the reaction diagram
-
-
-
-
?
cyclohexanol + ferricyanide
cyclohexanone + ferrocyanide
show the reaction diagram
-
enzyme electrode, 11% of vmax with 1-butanol, soluble enzyme, 9% of vmax with 1-butanol
-
-
?
ethanal + ferrocyanide
ethanol + ferricyanide
show the reaction diagram
ethanol + cytochrome c
ethanal + reduced cytochrome c
show the reaction diagram
-
5% of the activity with Wurster's Blue. In presence of phenazine methosulfate, 60% of the activity with Wurster's Blue
-
-
r
ethanol + ferricyanide
ethanal + ferrocyanide
show the reaction diagram
ethanol + N,N,N',N'-tetramethyl-p-phenylenediamine
ethanal + ?
show the reaction diagram
-
i.e. Wurster's Blue
-
-
?
ethanol + oxidized 2,6-dichlorophenolindophenol
ethanal + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
10% of the activity with Wurster's Blue. In presence of phenazine methosulfate, 75% of the activity with Wurster's Blue
-
-
r
formaldehyde + N,N,N',N'-tetramethyl-p-phenylenediamine
methanol + ?
show the reaction diagram
-
-
-
-
r
glycerol + ferrocyanide
2,3-dihydroxypropanal + ferricyanide
show the reaction diagram
-
ADH IIB, 0% of the activity with 1-butanol. ADH IIG, 63% of the activity with 1,2-propanediol
-
-
?
iso-amyl alcohol + ferricyanide
3-methylbutanol + ferrocyanide
show the reaction diagram
-
ADH IIB, 100% of the activity with 1-butanol. ADH IIG, 93% of the activity with 1,2-propanediol
-
-
?
n-butanol + ferricyanide
butanal + ferrocyanide
show the reaction diagram
-
-
-
-
?
octanal + reduced N,N,N',N'-tetramethyl-p-phenylenediamine
1-octanol + N,N,N',N'-tetramethyl-p-phenylenediamine
show the reaction diagram
-
-
-
-
r
propanal + ferrocyanide
1-propanol + ferricyanide
show the reaction diagram
-
ADH IIB, 125% of the activity with 1-butanol. ADH IIG, 58% of the activity with 1,2-propanediol
-
-
?
rac-2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane + ferricyanide
? + ferrocyanide
show the reaction diagram
-
i.e. solketal. Enantiomeric ratio is 30 for solketal and 6 for rac-2,2-dimethyl-4-[1,1-2H]hydroxymethyl-1,3-[5,5,4-2H]dioxolane, d5-solketal. Isotopic substitution affects the relative kinetic weights of the initial hydron/deuteron transfer from substrate to cofactor and the subsequent proton/deuteron shift in the cofactor-product complex
-
-
?
additional information
?
-