We're sorry, but BRENDA doesn't work properly without JavaScript. Please make sure you have JavaScript enabled in your browser settings.
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
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
+
2
reduced adrenodoxin
+
2
+
=
+
2
oxidized adrenodoxin
+
2
Synonyms
CYP27C1 , cytochrome P450 27C1,
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CYP27C1
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2 = all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
?
-
all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
?
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-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
-
-
-
?
all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2
all-trans-3,4-didehydroretinol + 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
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
cytochrome P450
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
-
UniProt
brenda
-
UniProt
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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 )
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Select items on the left to see more content.
html completed
BRENDA home
History
Enzyme Nomenclature
1.14.19.53 all-trans-retinol 3,4-desaturase
top
