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Information on EC 1.14.19.53 - all-trans-retinol 3,4-desaturase

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EC Tree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.19 With oxidation of a pair of donors resulting in the reduction of O₂ to two molecules of water

1.14.19.53 all-trans-retinol 3,4-desaturase

IUBMB Comments

A cytochrome P-450 (heme thiolate) enzyme found in vertebrates. The enzyme is also active with retinal and retinoic acid.

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1.14.19.53
retinal
retinoids
photoreceptors
red-shifted
zebrafish
chromophore
long-wavelength
tuning
epithelium
desaturated
orphan
vision

The enzyme appears in viruses and cellular organisms

Reaction Schemes

all-trans-3,4-didehydroretinol

oxidized adrenodoxin

H2O

reduced adrenodoxin

oxidized adrenodoxin

Synonyms

CYP27C1, cytochrome P450 27C1, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

CYP27C1

cytochrome P450 27C1

CYP27C1

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2 = all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Retinol metabolism

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SYSTEMATIC NAME

IUBMB Comments

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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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O

2 entries

all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O

2 entries

all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O

3 entries

additional information

2 entries

all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O

Danio rerio

A8WGA0

744751

all-trans-retinal + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinal + 2 oxidized adrenodoxin + 2 H2O

Homo sapiens

Q4G0S4

744905

all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O

Danio rerio

A8WGA0

744751

all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O

Homo sapiens

Q4G0S4

744905

all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O

Danio rerio

A8WGA0

744751

all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O

Homo sapiens

Q4G0S4

744905, 745368

all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2

all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O

Homo sapiens

745368

additional information

Homo sapiens

Q4G0S4

kinetic isotope effects of 1.5–2.3 (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

745368

additional information

Homo sapiens

745368

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

cytochrome P450

cytochrome P450

cytochrome P450

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.00035

all-trans-retinal

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

0.00087

all-trans-retinoic acid

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

0.0005 - 0.0011

all-trans-retinol

2 entries

0.0005

all-trans-retinol

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

0.0011

all-trans-retinol

pH 7.4, 37°C

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.004

all-trans-retinal

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

0.023

all-trans-retinoic acid

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

0.068 - 0.38

all-trans-retinol

2 entries

0.068

all-trans-retinol

Homo sapiens

Q4G0S4

pH 7.4, 37°C

745368

0.38

all-trans-retinol

Homo sapiens

Q4G0S4

pH 7.4, temperature not specified in the publication

744905

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kcat/KM VALUE [1/mMs^-1]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

800

all-trans-retinal

Danio rerio

A8WGA0

37°C, pH not specified in the publication

744751

800

all-trans-retinoic acid

Danio rerio

A8WGA0

37°C, pH not specified in the publication

744751

61 - 1900

all-trans-retinol

all-trans-retinol

pH 7.4, 37°C

1900

all-trans-retinol

Danio rerio

A8WGA0

37°C, pH not specified in the publication

744751

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Danio rerio

744751

A8WGA0

UniProt

brenda

Homo sapiens

744905, 745368

Q4G0S4

UniProt

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

physiological function

2 entries

physiological function

Danio rerio

A8WGA0

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

744751

physiological function

Homo sapiens

Q4G0S4

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

745368

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

SEQUENCE

LOCALIZATION PREDICTION

The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).

Q4G0S4 pBLAST

C27C1_HUMAN

Homo sapiens

542

60920

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 2)

P0DOX0 pBLAST

C27C1_LITCT

Lithobates catesbeianus

537

61621

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 1)

A8WGA0 pBLAST

C27C1_DANRE

Danio rerio

540

61492

Swiss-Prot

Show Sequence

other Location (Reliability: 5)

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

744751

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.

3048-3057

2015

Danio rerio (A8WGA0), Danio rerio

26549260

brenda

744905

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