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Literature summary for 1.1.1.326 extracted from

  • Okamoto, S.; Yu, F.; Harada, H.; Okajima, T.; Hattan, J.; Misawa, N.; Utsumi, R.
    A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet (2011), FEBS J., 278, 2892-2900.
    View publication on PubMed

Application

Application Comment Organism
pharmacology zerumbone is a predominating potential multi-anticancer agent Zingiber zerumbet

Cloned(Commentary)

Cloned (Comment) Organism
gene ZSD1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of wild-type and mutant enzymes in Escherichia coli strain BL21(DE3) Zingiber zerumbet

Protein Variants

Protein Variants Comment Organism
K159A site-directed mutagenesis, inactive mutant Zingiber zerumbet
S142A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Zingiber zerumbet
S144A site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme Zingiber zerumbet
Y155A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Zingiber zerumbet

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information kinetics with borneol as substrate Zingiber zerumbet
0.0161
-
NAD+ recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet
0.0273
-
NAD+ recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
0.028
-
10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet
0.0437
-
NAD+ recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
0.0585
-
10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
0.0782
-
10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
0.121
-
NAD+ recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet
0.138
-
10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
28700
-
x * 28700, sequence calculation Zingiber zerumbet

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
10-hydroxy-alpha-humulene + NAD+ Zingiber zerumbet
-
zerumbone + NADH + H+
-
?

Organism

Organism UniProt Comment Textmining
Zingiber zerumbet F1SWA0 gene ZSD1
-

Purification (Commentary)

Purification (Comment) Organism
recombinant wild-type and mutant enzymes from Escherichia coli strain Bl21(DE3) Zingiber zerumbet

Source Tissue

Source Tissue Comment Organism Textmining
leaf
-
Zingiber zerumbet
-
rhizome contains an exceptionally high level of sesquiterpenoids with zerumbone Zingiber zerumbet
-
stem
-
Zingiber zerumbet
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
10-hydroxy-alpha-humulene + NAD+
-
Zingiber zerumbet zerumbone + NADH + H+
-
?
10-hydroxy-alpha-humulene + NAD+ the enzyme possesses a flexible substrate-binding pocket and converts 10-hydroxy-alpha-humulene into zerumbone Zingiber zerumbet zerumbone + NADH + H+
-
?
additional information the enzyme also converts borneol to camphor in vitro with Km and kcat values of 0.0228 mM and 4.1/s Zingiber zerumbet ?
-
?

Subunits

Subunits Comment Organism
? x * 28700, sequence calculation Zingiber zerumbet
More a 3D structure model of ZSD1 reveals a large, flexible substrate-binding pocket, molecular modeling, overview Zingiber zerumbet

Synonyms

Synonyms Comment Organism
ZSD1
-
Zingiber zerumbet

Temperature Optimum [┬░C]

Temperature Optimum [┬░C] Temperature Optimum Maximum [┬░C] Comment Organism
37
-
assay at Zingiber zerumbet

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.1
-
NAD+ recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet
0.1
-
10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet
0.1
-
NAD+ recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
0.1
-
10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
1.3
-
10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
2.9
-
10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet
3.8
-
NAD+ recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
4.4
-
NAD+ recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
assay at Zingiber zerumbet

Cofactor

Cofactor Comment Organism Structure
NAD+ ZSD1 contains an NAD+-binding motif TGxxxGxG Zingiber zerumbet

pI Value

Organism Comment pI Value Maximum pI Value
Zingiber zerumbet sequence calculation
-
5.63

General Information

General Information Comment Organism
evolution ZSD1 is a member of the short-chain dehydrogenase/reductase superfamily, SDR, and shares high identities with other plant SDRs involved in secondary metabolism, stress responses and phytosteroid biosynthesis Zingiber zerumbet
metabolism ZSD1 is an alcohol dehydrogenase capable of catalyzing the final step of zerumbone biosynthesis, but ZSD1 is also be involved in other biological processes Zingiber zerumbet
additional information the enzyme contains an active site sequence 155Y-X-X-X-K159, Ser142 completes the Ser-Tyr-Lys triad responsible for the catalysis of ZSD1 Zingiber zerumbet
physiological function ZSD1 is involved in secondary metabolism, stress responses and phytosteroid biosynthesis Zingiber zerumbet

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0000007
-
10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet
0.0000008
-
NAD+ recombinant mutant S142A, pH 8.0, 37┬░C Zingiber zerumbet
0.000001
-
10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
0.000002
-
NAD+ recombinant mutant Y155A, pH 8.0, 37┬░C Zingiber zerumbet
0.000022
-
10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
0.000103
-
10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet
0.000139
-
NAD+ recombinant wild-type enzyme, pH 8.0, 37┬░C Zingiber zerumbet
0.000262
-
NAD+ recombinant mutant S144A, pH 8.0, 37┬░C Zingiber zerumbet