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IUBMB Comments A cytochrome P-450 (heme thiolate) enzyme found in vertebrates. The enzyme is also active with retinal and retinoic acid.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
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2
reduced adrenodoxin
+
2
+
=
+
2
oxidized adrenodoxin
+
2
Synonyms
CYP27C1 , cytochrome P450 27C1,
more
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CYP27C1
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all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2 = all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinol,reduced adrenodoxin:oxygen 3,4-oxidoreductase
A cytochrome P-450 (heme thiolate) enzyme found in vertebrates. The enzyme is also active with retinal and retinoic acid.
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all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O
all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O
all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
additional information
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all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
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all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
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additional information
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kinetic isotope effects of 1.5â2.3 (on kcat/Km) are observed with 3,3-, 4,4-, and 3,3,4,4-deuterated retinol. Deuteration at C-4 produces a 4fold increase in 3-hydroxylation due to metabolic switching, with no observable effect on 4-hydroxylation. Deuteration at C-3 produces a strong kinetic isotope effect for 3-hydroxylation but not 4-hydroxylation
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additional information
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kinetic isotope effects of 1.5â2.3 (on kcat/Km) are observed with 3,3-, 4,4-, and 3,3,4,4-deuterated retinol. Deuteration at C-4 produces a 4fold increase in 3-hydroxylation due to metabolic switching, with no observable effect on 4-hydroxylation. Deuteration at C-3 produces a strong kinetic isotope effect for 3-hydroxylation but not 4-hydroxylation
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cytochrome P450
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0.00035
all-trans-retinal
pH 7.4, temperature not specified in the publication
0.00087
all-trans-retinoic acid
pH 7.4, temperature not specified in the publication
0.0005 - 0.0011
all-trans-retinol
0.0005
all-trans-retinol
pH 7.4, temperature not specified in the publication
0.0011
all-trans-retinol
pH 7.4, 37°C
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0.004
all-trans-retinal
pH 7.4, temperature not specified in the publication
0.023
all-trans-retinoic acid
pH 7.4, temperature not specified in the publication
0.068 - 0.38
all-trans-retinol
0.068
all-trans-retinol
pH 7.4, 37°C
0.38
all-trans-retinol
pH 7.4, temperature not specified in the publication
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800
all-trans-retinal
37°C, pH not specified in the publication
800
all-trans-retinoic acid
37°C, pH not specified in the publication
61 - 1900
all-trans-retinol
61
all-trans-retinol
pH 7.4, 37°C
1900
all-trans-retinol
37°C, pH not specified in the publication
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UniProt
brenda
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UniProt
brenda
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brenda
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physiological function
knockout of Cyp27c1 in zebrafish abrogates production of vitamin A2, eliminates the animal's ability to red-shift its photoreceptor spectral sensitivity, and reduces its ability to see and respond to near-infrared light
physiological function
the most likely catalytic mechanism begins with abstraction of a hydrogen atom from C-4 (or possibly C-3) initiating the desaturation pathway, followed by a sequential abstraction of a hydrogen atom or proton-coupled electron transfer. Adrenodoxin reduction and hydrogen abstraction both contribute to rate limitation
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C27C1_DANRE
540
0
61492
Swiss-Prot
other Location (Reliability: 5 )
C27C1_HUMAN
542
0
60920
Swiss-Prot
Mitochondrion (Reliability: 2 )
C27C1_LITCT
537
0
61621
Swiss-Prot
Mitochondrion (Reliability: 1 )
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Enright, J.M.; Toomey, M.B.; Sato, S.Y.; Temple, S.E.; Allen, J.R.; Fujiwara, R.; Kramlinger, V.M.; Nagy, L.D.; Johnson, K.M.; Xiao, Y.; How, M.J.; Johnson, S.L.; Roberts, N.W.; Kefalov, V.J.; Guengerich, F.P.; Corbo, J.C.
Cyp27c1 red-shifts the spectral sensitivity of photoreceptors by converting vitamin A1 into A2
Curr. Biol.
25
3048-3057
2015
Danio rerio (A8WGA0), Danio rerio
brenda
Kramlinger, V.; Nagy, L.; Fujiwara, R.; Johnson, K.; Phan, T.; Xiao, Y.; Enright, J.; Toomey, M.; Corbo, J.; Guengerich, F.
Human cytochrome P450 27C1 catalyzes 3,4-desaturation of retinoids
FEBS Lett.
590
1304-1312
2016
Homo sapiens (Q4G0S4), Homo sapiens
brenda
Johnson, K.; Phan, T.; Albertolle, M.; Peter Guengerich, F.
Human mitochondrial cytochrome P450 27C1 is localized in skin and preferentially desaturates trans-retinol to 3,4-dehydroretinol
J. Biol. Chem.
292
13672-13687
2017
Homo sapiens (Q4G0S4), Homo sapiens
brenda
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