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EC Tree
IUBMB Comments The enzyme, characterized from the bacterium Sterolibacterium denitrificans, participates in the anaerobic degradation of cholesterol. The enzyme can accept several substrates including vitamin D3. The enzyme contains a bis(guanylyl molybdopterin) cofactor, five [Fe-S] clusters, and one heme b. cf. EC 1.14.99.38, cholesterol 25-monooxygenase, an oxygen-requiring eukaryotic enzyme that catalyses a similar transformation.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
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25-hydroxycholest-4-en-3-one
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Synonyms
s25dh, steroid c25 dehydrogenase, s25dh1, c25 dehydrogenase, s25dh3, d3 25-hydroxylase, steroid c-25 dehydrogenase,
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cholesterol C-25 dehydrogenase
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steroid C-25 dehydrogenase
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steroid C25 dehydrogenase
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vitamin D3 25-hydroxylase
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cholest-4-en-3-one + acceptor + H2O = 25-hydroxycholest-4-en-3-one + reduced acceptor
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cholest-4-en-3-one:acceptor oxidoreductase (25-hydroxylating)
The enzyme, characterized from the bacterium Sterolibacterium denitrificans, participates in the anaerobic degradation of cholesterol. The enzyme can accept several substrates including vitamin D3. The enzyme contains a bis(guanylyl molybdopterin) cofactor, five [Fe-S] clusters, and one heme b. cf. EC 1.14.99.38, cholesterol 25-monooxygenase, an oxygen-requiring eukaryotic enzyme that catalyses a similar transformation.
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5-cholesten-3beta-ol-7-one + acceptor + H2O
25-hydroxy-5-cholesten-3beta-ol-7-one + reduced acceptor
15% of the activity as compared to activity with cholest-4-en-3-one
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7-dehydrocholesterol + acceptor + H2O
25-hydroxy-7-dehydrocholesterol + reduced acceptor
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high activity with isoenzyme S25DH2, low activity with isoenzyme S25DH1. No activity with isoenzyme S25DH1, S25DH2 and S25DH3
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beta-sitost-4-en-3-one + acceptor + H2O
25-hydroxysitost-4-en-3-one + reduced acceptor
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high activity with isoenzyme S25DH4. No activity with isoenzyme S25DH1 and S25DH2
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campest-4-en-3-one + acceptor + H2O
25-hydroxycampest-4-en-3-one + reduced acceptor
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high activity with isoenzyme S25DH4, low activity with isoenzyme S25DH3. No activity with isoenzyme S25DH1 and S25DH2
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cholecalciferol + acceptor + H2O
25-hydroxycholecalciferol + reduced acceptor
cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
cholesta-1,4-dien-3-one + acceptor + H2O
25-hydroxycholesta-1,4-dien-3-one + reduced acceptor
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90% concversion after 4 h
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cholesta-4,6-dien-3-one + acceptor + H2O
25-hydroxycholesta-4,6-dien-3-one + reduced acceptor
127% of the activity as compared to activity with cholest-4-en-3-one
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cholesterol + acceptor + H2O
25-hydroxycholesterol + reduced acceptor
vitamin D3 + acceptor + H2O
25-hydroxy-vitamin D3 + reduced acceptor
cholecalciferol + acceptor + H2O
25-hydroxycholecalciferol + reduced acceptor
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the product 25-hydroxycholecalciferol (calcifediol) is the activated form of vitamin D3 used in the treatment of rickets and other calcium disorders
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cholecalciferol + acceptor + H2O
25-hydroxycholecalciferol + reduced acceptor
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90% concversion after 46 h
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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90% concversion after 4 h
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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high activity with isoenzymes S25DH1, S25DH2 and S25DH1. No activity with isoenzyme S25DH3
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cholesterol + acceptor + H2O
25-hydroxycholesterol + reduced acceptor
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cholesterol + acceptor + H2O
25-hydroxycholesterol + reduced acceptor
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the product 25-hydroxycholesterol is responsible for a complex regulatory function in the immunological system
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cholesterol + acceptor + H2O
25-hydroxycholesterol + reduced acceptor
10% of the activity as compared to activity with cholest-4-en-3-one
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vitamin D3 + acceptor + H2O
25-hydroxy-vitamin D3 + reduced acceptor
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vitamin D3 + acceptor + H2O
25-hydroxy-vitamin D3 + reduced acceptor
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high activity with isoenzyme S25DH1, low activity with isoenzyme S25DH2. No activity with isoenzyme S25DH3 and S25DH4
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cholecalciferol + acceptor + H2O
25-hydroxycholecalciferol + reduced acceptor
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the product 25-hydroxycholecalciferol (calcifediol) is the activated form of vitamin D3 used in the treatment of rickets and other calcium disorders
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
cholesterol + acceptor + H2O
25-hydroxycholesterol + reduced acceptor
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the product 25-hydroxycholesterol is responsible for a complex regulatory function in the immunological system
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vitamin D3 + acceptor + H2O
25-hydroxy-vitamin D3 + reduced acceptor
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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cholest-4-en-3-one + acceptor + H2O
25-hydroxycholest-4-en-3-one + reduced acceptor
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heme b
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the enzyme contains heme B
[3Fe-4S]-center
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the enzyme contains one [3Fe-4S] cluster
[4Fe-4S]-center
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the enzyme contains four [4Fe-4S] clusters
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Mo2+
molybdoenzyme
Mo2+
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the enzyme contains molybdenum
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0.123
7-dehydrocholesterol
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isoenzyme S25DH2, pH 7.0, 30°C
0.12
beta-sitost-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.34 - 1.84
campest-4-en-3-one
0.124 - 0.45
cholest-4-en-3-one
0.0000145 - 0.29
vitamin D3
0.34
campest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
1.84
campest-4-en-3-one
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isoenzyme S25DH3, pH 7.0, 30°C
0.124
cholest-4-en-3-one
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isoenzyme S25DH2, pH 7.0, 30°C
0.39
cholest-4-en-3-one
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isoenzyme S25DH1, pH 7.0, 30°C
0.45
cholest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.0000145
vitamin D3
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pH 7.5, 37°C
0.29
vitamin D3
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isoenzyme S25DH1, pH 7.0, 30°C
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0.33
7-dehydrocholesterol
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isoenzyme S25DH2, pH 7.0, 30°C
0.14
beta-sitost-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.018 - 0.17
campest-4-en-3-one
0.21 - 1.11
cholest-4-en-3-one
0.23
vitamin D3
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isoenzyme S25DH1, pH 7.0, 30°C
0.018
campest-4-en-3-one
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isoenzyme S25DH3, pH 7.0, 30°C
0.17
campest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.21
cholest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.29
cholest-4-en-3-one
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isoenzyme S25DH2, pH 7.0, 30°C
1.11
cholest-4-en-3-one
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isoenzyme S25DH1, pH 7.0, 30°C
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2.7
7-dehydrocholesterol
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isoenzyme S25DH2, pH 7.0, 30°C
1.2
beta-sitost-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.01 - 0.5
campest-4-en-3-one
0.46 - 2.8
cholest-4-en-3-one
0.79
vitamin D3
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isoenzyme S25DH1, pH 7.0, 30°C
0.01
campest-4-en-3-one
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isoenzyme S25DH3, pH 7.0, 30°C
0.5
campest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
0.46
cholest-4-en-3-one
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isoenzyme S25DH4, pH 7.0, 30°C
2.3
cholest-4-en-3-one
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isoenzyme S25DH2, pH 7.0, 30°C
2.8
cholest-4-en-3-one
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isoenzyme S25DH1, pH 7.0, 30°C
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additional information
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immobilization of the enzyme either on powder or a monolithic silica support functionalized with an organic linker providing NH2 groups for enzyme covalent binding reduces the initial activity of the enzyme more than twofold
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brenda
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brenda
H9NN89: steroid C25 dehydrogenase alpha subunit, H9NN90: steroid C25 dehydrogenase beta subunit, H9NN91: steroid C25 dehydrogenase gamma subunit
UniProt
brenda
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brenda
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brenda
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brenda
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160000
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gel filtration, isoenzyme S25DH4
167000
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gel filtration, isoenzyme S25DH, isoenzyme S25DH2, isoenzyme S25DH4
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dodecamer
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alpha4beta4gamma4, isoenzyme S25DH4
nonamer
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alpha3beta3gamma3, isoenzyme S25DH3
octamer
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alpha2beta3gamma3, isoenzyme S25DH2
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immobilization of the enzyme either on powder or a monolithic silica support functionalized with an organic linker providing NH2 groups for enzyme covalent binding extends the catalytic lifetime of the enzyme under working conditions at least 3.5times
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in the presence of 5 mM K3[Fe(CN)6], activity expressed in Thauera aromatica crude extracts is stable in air at 30°C for 5 to 8 h but decreased to 50% after 24 h
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purified enzyme is inactivated irreversibly by incubation in air with a half-life of 14 min. The inactivation is largely prevented by the addition of the artificial electron acceptor potassium hexacyanoferrate (III) to the enzyme preparation. In the presence of cyanoferrate, more than 90% of the enzyme activity is retained after a 2 h incubation in air. The enzymatic activity is completely lost after 24 h of incubation
759470
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the enzyme can be stored for at least 3 months at 4 °C under anaerobic conditions
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a heterologous expression platform is established for the three structural genes of S25DH subunits together with an essential chaperone in the denitrifying betaproteobacterium Thauera aromatica K172. Using this system, steroid C-25 dehydrogenase S25DH1 and three isoenzymes (S25DH2, S25DH3, and S25DH4) are overproduced in a soluble, active form allowing a straightforward purification of nontagged alphabetagamma complexes
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Rugor, A.; Tataruch, M.; Staron, J.; Dudzik, A.; Niedzialkowska, E.; Nowak, P.; Hogendorf, A.; Michalik-Zym, A.; Napruszewska, D.; Jarzebski, A.; Szymanska, K.; Bialas, W.; Szaleniec, M.
Regioselective hydroxylation of cholecalciferol, cholesterol and other sterol derivatives by steroid C25 dehydrogenase
Appl. Microbiol. Biotechnol.
101
1163-1174
2017
Sterolibacterium denitrificans
brenda
Dermer, J.; Fuchs, G.
Molybdoenzyme that catalyzes the anaerobic hydroxylation of a tertiary carbon atom in the side chain of cholesterol
J. Biol. Chem.
287
36905-36916
2012
Sterolibacterium denitrificans (H9NN89 AND H9NN90 AND H9NN91), Sterolibacterium denitrificans
brenda
Jacoby, C.; Eipper, J.; Warnke, M.; Tiedt, O.; Mergelsberg, M.; Staerk, H.J.; Daus, B.; Martin-Moldes, Z.; Zamarro, M.T.; Diaz, E.; Boll, M.
Four molybdenum-dependent steroid C-25 hydroxylases heterologous overproduction, role in steroid degradation, and application for 25-hydroxyvitamin D3 synthesis
mBio
9
e00694-18
2018
Sterolibacterium denitrificans
brenda
Gascon-Barre, M.; Elbaz, H.; Therrien-Ferland, D.
Sequestration and microsomal C-25 hydroxylation of [3H]-vitamin D3 by the rat liver
Metabolism
34
244-250
1985
Rattus norvegicus
brenda
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