1.1.9.1: alcohol dehydrogenase (azurin)

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

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

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

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

703526

(R)-glycidol + ferrocyanide

? + ferricyanide

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+

(R)-enantiomer is prefered, enantiomeric ratio is 30

703526

(R)-solketal + ferrocyanide

? + ferricyanide

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

(S)-2-butanol + ferricyanide

butan-2-one + ferrocyanide

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

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

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

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

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+

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

703526

(S)-solketal + ferrocyanide

? + ferricyanide

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

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

1,2-ethanediol + ferricyanide

hydroxyacetaldehyde + ferrocyanide

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

ADH IIB, 43% of the activity with 1-butanol. ADH IIG, maximum activity

1,3-butanediol + ferricyanide

3-hydroxybutanal + ferrocyanide

ADH IIB, 105% of the activity with 1-butanol. ADH IIG, 75% of the activity with 1,2-propanediol

1,3-butanediol + ferricyanide

? + ferrocyanide

enzyme electrode, 91% of vmax with 1-butanol

1,3-cyclohexanediol + ferricyanide

3-hydroxycyclohexanone + ferrocyanide

1,3-propandione + ferricyanide

3-hydroxypropanal + ferrocyanide

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

ADH IIB, 110% of the activity with 1-butanol. ADH IIG, 75% of the activity with 1,2-propanediol

1-butanol + ferricyanide

butanal + ferrocyanide

3 entries

1-butanol + N,N,N',N'-tetramethyl-p-phenylenediamine

butanal + ?

1-heptanol + ferricyanide

heptanal + ferrocyanide

ADH IIB, 99% of the activity with 1-butanol. ADH IIG, 39% of the activity with 1,2-propanediol

1-hexanol + ferricyanide

hexanal + ferrocyanide

ADH IIB, 70% of the activity with 1-butanol. ADH IIG, 46% of the activity with 1,2-propanediol

1-octanol + ferricyanide

octanal + ferrocyanide

1-octanol + ferrocyanide

octanal + ferricyanide

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 + ?

1-pentanol + ferricyanide

pentanal + ferrocyanide

1-pentanol + ferrocyanide

pentanal + ferricyanide

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 + ?

1-propanol + ferricyanide

propanal + ferrocyanide

3 entries

1-propanol + N,N,N',N'-tetramethyl-p-phenylenediamine

propanal + ?

2,3-butanediol + ferricyanide

3-hydroxybutan-2-one + ferrocyanide

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

ADH IIB, 45% of the activity with 1-butanol. ADH IIG, 0% of the activity with 1,2-propanediol

2-butanol + ferricyanide

butanone + ferrocyanide

2-butanol + ferrocyanide

butanone + ferricyanide

enzyme electrode, 17% of vmax with 1-butanol, soluble enzyme, 10% of vmax with 1-butanol

2-hexanol + ferricyanide

hexan-2-one + ferrocyanide

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

2-octanol + ferricyanide

octan-2-one + ferrocyanide

2-octanol + ferrocyanide

octan-2-one + ferricyanide

enzyme electrode, 84% of vmax with 1-butanol, soluble enzyme, 80% of vmax with 1-butanol

2-pentanol + ferricyanide

pentan-2-one + ferrocyanide

2-pentanol + ferrocyanide

pentan-2-one + ferricyanide

enzyme electrode, 40% of vmax with 1-butanol, soluble enzyme, 34% of vmax with 1-butanol

2-propanol + ferricyanide

acetone + ferrocyanide

2-propanol + ferrocyanide

acetone + ferricyanide

enzyme electrode, 9% of vmax with 1-butanol, soluble enzyme, 6% of vmax with 1-butanol

3-heptanol + ferricyanide

heptan-3-one + ferrocyanide

3-heptanol + ferrocyanide

heptan-3-one + ferricyanide

enzyme electrode, 3.7% of vmax with 1-butanol, soluble enzyme, 1% of vmax with 1-butanol

3-hexanol + ferricyanide

hexan-3-one + ferrocyanide

3-hexanol + ferrocyanide

hexan-3-one + ferricyanide

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

3-methylcyclohexanol + ferricyanide

3-methylcyclohexanone + ferrocyanide

3-nonanol + ferricyanide

nonan-3-one + ferrocyanide

3-octanol + ferricyanide

octan-3-one + ferrocyanide

3-octanol + ferrocyanide

octan-3-one + ferricyanide

enzyme electrode, 10% of vmax with 1-butanol, soluble enzyme, 10% of vmax with 1-butanol

3-pentanol + ferricyanide

pentan-3-one + ferrocyanide

3-pentanol + ferrocyanide

pentan-3-one + ferricyanide

enzyme electrode, 1% of vmax with 1-butanol, soluble enzyme, 1.4% of vmax with 1-butanol

4-decanol + ferricyanide

decan-4-one + ferrocyanide

4-heptanol + ferricyanide

heptan-4-one + ferrocyanide

4-methyl-2-pentanol + ferricyanide

4-methylpentan-2-one + ferrocyanide

enzyme electrode, 5.6% of vmax with 1-butanol

5-methyl-2-hexanol + ferricyanide

5-methylhexan-2-one + ferrocyanide

6-aminohexan-1-ol + N,N,N',N'-tetramethyl-p-phenylenediamine

6-aminohexanal + ?

acetaldehyde + reduced N,N,N',N'-tetramethyl-p-phenylenediamine

ethanol + N,N,N',N'-tetramethyl-p-phenylenediamine

allyl alcohol + ferricyanide

prop-2-enal + ferrocyanide

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 + ?

butanal + ferrocyanide

1-butanol + ferricyanide

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

butane-1,3-diol + N,N,N',N'-tetramethyl-p-phenylenediamine

cyclohexanol + ferricyanide

cyclohexanal + ferrocyanide

cyclohexanol + ferricyanide

cyclohexanone + ferrocyanide

enzyme electrode, 11% of vmax with 1-butanol, soluble enzyme, 9% of vmax with 1-butanol

ethanal + ferrocyanide

ethanol + ferricyanide

ethanol + cytochrome c

ethanal + reduced cytochrome c

5% of the activity with Wurster's Blue. In presence of phenazine methosulfate, 60% of the activity with Wurster's Blue

ethanol + ferricyanide

ethanal + ferrocyanide

5 entries

ethanol + N,N,N',N'-tetramethyl-p-phenylenediamine

ethanal + ?

i.e. Wurster's Blue

ethanol + oxidized 2,6-dichlorophenolindophenol

ethanal + reduced 2,6-dichlorophenolindophenol

10% of the activity with Wurster's Blue. In presence of phenazine methosulfate, 75% of the activity with Wurster's Blue

formaldehyde + N,N,N',N'-tetramethyl-p-phenylenediamine

methanol + ?

glycerol + ferrocyanide

2,3-dihydroxypropanal + ferricyanide

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

ADH IIB, 100% of the activity with 1-butanol. ADH IIG, 93% of the activity with 1,2-propanediol

n-butanol + ferricyanide

butanal + ferrocyanide

389960

octanal + reduced N,N,N',N'-tetramethyl-p-phenylenediamine

1-octanol + N,N,N',N'-tetramethyl-p-phenylenediamine

propanal + ferrocyanide

1-propanol + ferricyanide

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

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

654868

additional information