Literature summary extracted from

  • Hirata, T.; Tamura, Y.; Yokobatake, N.; Shimoda, K.; Ashida, Y.
    A 38 kDa allylic alcohol dehydrogenase from the cultured cells of Nicotiana tabacum (2000), Phytochemistry, 55, 297-303.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Commentary) Organism
1.1.1.54 sequence homology with other NADPH-dependent oxidoreductases from plants Nicotiana tabacum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Commentary Organism Structure
1.3.1.102 additional information
-
additional information the Km-values for the (S)-alcohols are one order of magnitude lower than those for the (R)-alcohols, indicating that the enzyme has a higher affinity for the S-configuration than for the R-configuration Nicotiana tabacum
1.3.1.102 1.9
-
(2S,4R)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 2.5
-
(2S,4S)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 38
-
(2R,4R)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 52
-
(2R,4S)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 590
-
(1R,2S,4S)-neoisodihydrocarveol pH 8.0, 35°C, NADP+ Nicotiana tabacum

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Commentary Organism
1.1.1.54 74000
-
gel filtration Nicotiana tabacum
1.3.1.102 74000
-
approximately, gel filtration chromatography on a TSK G3000SW HPLC column Nicotiana tabacum
1.1.1.54 37000
-
2 * 37000, SDS-PAGE and amino acid sequence analysis Nicotiana tabacum
1.3.1.102 37000
-
alpha2, 2 * 37000, determined by SDS-PAGE Nicotiana tabacum
1.3.1.102 38080
-
allyl-ADH1, calculated from sequence Nicotiana tabacum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Commentary (Nat. Sub.) Natural Products Commentary (Nat. Pro.) Organism (Nat. Pro.) Reversibility ID
1.1.1.54 allyl alcohol + NADP+ Nicotiana tabacum
-
acrolein + NADPH
-
-
r

Organism

EC Number Organism UniProt Commentary Textmining
1.1.1.54 Nicotiana tabacum
-
-
-
1.3.1.102 Nicotiana tabacum Q9SLN8
-
-

Purification (Commentary)

EC Number Purification (Commentary) Organism
1.1.1.54
-
Nicotiana tabacum
1.3.1.102 by DEAE-Toyopearl anion exchange column chromatography, followed by Red-Toyopearl affinity column chromatography Nicotiana tabacum

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Commentary Organism
1.1.1.54 0.11
-
-
Nicotiana tabacum
1.3.1.102 0.11
-
Red-Toyopearl affinity column chromatography, pH 8.0, 35°C Nicotiana tabacum
1.3.1.102 4.6
-
DEAE-Toyopearl anion exchange column chromatography, pH 8.0, 35°C Nicotiana tabacum
1.3.1.102 5300
-
crude extract, pH 8.0, 35°C Nicotiana tabacum

Substrates and Products (Substrate)

EC Number Substrates Commentary Substrates Literature (Substrates) Organism Products Commentary (Products) Literature (Products) Organism (Products) Reversibility Substrate Product ID
1.1.1.54 (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH
-
287113 Nicotiana tabacum r
1.1.1.54 (S)-carvone + NADPH
-
287113 Nicotiana tabacum (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum r
1.1.1.54 allyl alcohol + NADP+
-
287113 Nicotiana tabacum acrolein + NADPH
-
-
-
r
1.1.1.54 allyl alcohol + NADP+ specific for the (S)-isomer of secondary allylic alcohols, several stereomers tested for activity in both reaction directions 287113 Nicotiana tabacum acrolein + NADPH
-
-
-
r
1.3.1.102 (1R,2S,4S)-neoisodihydrocarveol + NADP+
-
287113 Nicotiana tabacum (1R,4S)-isodihydrocarvone + NADPH + H+
-
-
-
r
1.3.1.102 (2R,4R)-carveol + NADP+
-
287113 Nicotiana tabacum (R)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2R,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2S,4R)-carveol + NADP+
-
287113 Nicotiana tabacum (R)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 additional information results indicate that the enzyme catalyzes specifically the dehydrogenation of the secondary alcohols adjacent to the C-C double bond, no oxidation of saturated alcohols 287113 Nicotiana tabacum ?
-
-
-
?
1.3.1.102 additional information the enzymatic reaction is a reversible oxidoreduction and the reaction is enantioselective 287113 Nicotiana tabacum ?
-
-
-
?

Subunits

EC Number Subunits Commentary Organism
1.1.1.54 dimer 2 * 37000, SDS-PAGE and amino acid sequence analysis Nicotiana tabacum
1.3.1.102 homodimer alpha2, 2 * 37000, determined by SDS-PAGE Nicotiana tabacum

Synonyms

EC Number Synonyms Commentary Organism
1.3.1.102 allyl-ADH
-
Nicotiana tabacum
1.3.1.102 allyl-ADH1 the amino acid sequences of the deduced allyl-ADHs are different in four amino acid residues Nicotiana tabacum
1.3.1.102 allyl-ADH2 the amino acid sequences of the deduced allyl-ADHs are different in four amino acid residues, allyl-ADH2 has the following mutations compared to ADH1: T17A, V30A, L345P,R278H Nicotiana tabacum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Commentary Organism Structure
1.3.1.102 0.003
-
(1R,2S,4S)-neoisodihydrocarveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.003
-
(1R,4S)-isodihydrocarvone hydrogenation to (1R,2S,4S)-neoisodihydrocarveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.01
-
(S)-carvone hydrogenation to (2R,4S)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.012
-
(R)-carvone hydrogenation to (2R,4R)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.02
-
(2R,4R)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.025
-
(2R,4S)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.025
-
(S)-carvone hydrogenation to (2S,4S)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.032
-
(R)-carvone hydrogenation to (2S,4R)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.077
-
(2S,4S)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.097
-
(2S,4R)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Commentary Organism
1.1.1.54 7.4
-
reduction of carbonyl group of (S)-carvone Nicotiana tabacum
1.1.1.54 8
-
dehydrogenation of (S)-carveol Nicotiana tabacum
1.3.1.102 7.4
-
reduction of the carbonyl group of (S)-carvone Nicotiana tabacum
1.3.1.102 8
-
dehydrogenation of (2S,4S)-carveol Nicotiana tabacum

Cofactor

EC Number Cofactor Commentary Organism Structure
1.1.1.54 NAD(P)H
-
Nicotiana tabacum
1.1.1.54 NADP+ activity 4times greater than with NAD+ Nicotiana tabacum
1.3.1.102 NAD+ utilization of NADP+ by the enzyme is four times greater than for NAD+ Nicotiana tabacum
1.3.1.102 NADP+ utilization of NADP+ by the enzyme is four times greater than for NAD+ Nicotiana tabacum

Cloned(Commentary) (protein specific)

EC Number Commentary Organism
1.1.1.54 sequence homology with other NADPH-dependent oxidoreductases from plants Nicotiana tabacum

Cofactor (protein specific)

EC Number Cofactor Commentary Organism Structure
1.1.1.54 NAD(P)H
-
Nicotiana tabacum
1.1.1.54 NADP+ activity 4times greater than with NAD+ Nicotiana tabacum
1.3.1.102 NAD+ utilization of NADP+ by the enzyme is four times greater than for NAD+ Nicotiana tabacum
1.3.1.102 NADP+ utilization of NADP+ by the enzyme is four times greater than for NAD+ Nicotiana tabacum

KM Value [mM] (protein specific)

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Commentary Organism Structure
1.3.1.102 additional information
-
additional information the Km-values for the (S)-alcohols are one order of magnitude lower than those for the (R)-alcohols, indicating that the enzyme has a higher affinity for the S-configuration than for the R-configuration Nicotiana tabacum
1.3.1.102 1.9
-
(2S,4R)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 2.5
-
(2S,4S)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 38
-
(2R,4R)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 52
-
(2R,4S)-carveol pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 590
-
(1R,2S,4S)-neoisodihydrocarveol pH 8.0, 35°C, NADP+ Nicotiana tabacum

Molecular Weight [Da] (protein specific)

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Commentary Organism
1.1.1.54 74000
-
gel filtration Nicotiana tabacum
1.3.1.102 74000
-
approximately, gel filtration chromatography on a TSK G3000SW HPLC column Nicotiana tabacum
1.1.1.54 37000
-
2 * 37000, SDS-PAGE and amino acid sequence analysis Nicotiana tabacum
1.3.1.102 37000
-
alpha2, 2 * 37000, determined by SDS-PAGE Nicotiana tabacum
1.3.1.102 38080
-
allyl-ADH1, calculated from sequence Nicotiana tabacum

Natural Substrates/ Products (Substrates) (protein specific)

EC Number Natural Substrates Organism Commentary (Nat. Sub.) Natural Products Commentary (Nat. Pro.) Organism (Nat. Pro.) Reversibility ID
1.1.1.54 allyl alcohol + NADP+ Nicotiana tabacum
-
acrolein + NADPH
-
-
r

Purification (Commentary) (protein specific)

EC Number Commentary Organism
1.1.1.54
-
Nicotiana tabacum
1.3.1.102 by DEAE-Toyopearl anion exchange column chromatography, followed by Red-Toyopearl affinity column chromatography Nicotiana tabacum

Specific Activity [micromol/min/mg] (protein specific)

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Commentary Organism
1.1.1.54 0.11
-
-
Nicotiana tabacum
1.3.1.102 0.11
-
Red-Toyopearl affinity column chromatography, pH 8.0, 35°C Nicotiana tabacum
1.3.1.102 4.6
-
DEAE-Toyopearl anion exchange column chromatography, pH 8.0, 35°C Nicotiana tabacum
1.3.1.102 5300
-
crude extract, pH 8.0, 35°C Nicotiana tabacum

Substrates and Products (Substrate) (protein specific)

EC Number Substrates Commentary Substrates Literature (Substrates) Organism Products Commentary (Products) Literature (Products) Organism (Products) Reversibility ID
1.1.1.54 (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH
-
287113 Nicotiana tabacum r
1.1.1.54 (S)-carvone + NADPH
-
287113 Nicotiana tabacum (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum r
1.1.1.54 allyl alcohol + NADP+
-
287113 Nicotiana tabacum acrolein + NADPH
-
-
-
r
1.1.1.54 allyl alcohol + NADP+ specific for the (S)-isomer of secondary allylic alcohols, several stereomers tested for activity in both reaction directions 287113 Nicotiana tabacum acrolein + NADPH
-
-
-
r
1.3.1.102 (1R,2S,4S)-neoisodihydrocarveol + NADP+
-
287113 Nicotiana tabacum (1R,4S)-isodihydrocarvone + NADPH + H+
-
-
-
r
1.3.1.102 (2R,4R)-carveol + NADP+
-
287113 Nicotiana tabacum (R)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2R,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2S,4R)-carveol + NADP+
-
287113 Nicotiana tabacum (R)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 (2S,4S)-carveol + NADP+
-
287113 Nicotiana tabacum (S)-carvone + NADPH + H+
-
-
-
r
1.3.1.102 additional information results indicate that the enzyme catalyzes specifically the dehydrogenation of the secondary alcohols adjacent to the C-C double bond, no oxidation of saturated alcohols 287113 Nicotiana tabacum ?
-
-
-
?
1.3.1.102 additional information the enzymatic reaction is a reversible oxidoreduction and the reaction is enantioselective 287113 Nicotiana tabacum ?
-
-
-
?

Subunits (protein specific)

EC Number Subunits Commentary Organism
1.1.1.54 dimer 2 * 37000, SDS-PAGE and amino acid sequence analysis Nicotiana tabacum
1.3.1.102 homodimer alpha2, 2 * 37000, determined by SDS-PAGE Nicotiana tabacum

Turnover Number [1/s] (protein specific)

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Commentary Organism Structure
1.3.1.102 0.003
-
(1R,2S,4S)-neoisodihydrocarveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.003
-
(1R,4S)-isodihydrocarvone hydrogenation to (1R,2S,4S)-neoisodihydrocarveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.01
-
(S)-carvone hydrogenation to (2R,4S)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.012
-
(R)-carvone hydrogenation to (2R,4R)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.02
-
(2R,4R)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.025
-
(2R,4S)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.025
-
(S)-carvone hydrogenation to (2S,4S)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.032
-
(R)-carvone hydrogenation to (2S,4R)-carveol, pH 7.4, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.077
-
(2S,4S)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum
1.3.1.102 0.097
-
(2S,4R)-carveol dehydrogenation, pH 8.0, 35°C, NADP+ Nicotiana tabacum

pH Optimum (protein specific)

EC Number pH Optimum Minimum pH Optimum Maximum Commentary Organism
1.1.1.54 7.4
-
reduction of carbonyl group of (S)-carvone Nicotiana tabacum
1.1.1.54 8
-
dehydrogenation of (S)-carveol Nicotiana tabacum
1.3.1.102 7.4
-
reduction of the carbonyl group of (S)-carvone Nicotiana tabacum
1.3.1.102 8
-
dehydrogenation of (2S,4S)-carveol Nicotiana tabacum