Information on EC 1.14.19.25 - acyl-lipid omega-3 desaturase (cytochrome b5)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.19.25
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RECOMMENDED NAME
GeneOntology No.
acyl-lipid omega-3 desaturase (cytochrome b5)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
alpha-linolenate biosynthesis I (plants and red algae)
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hydroxylated fatty acid biosynthesis (plants)
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icosapentaenoate biosynthesis III (fungi)
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phospholipid desaturation
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SYSTEMATIC NAME
IUBMB Comments
(9Z,12Z)-octadeca-9,12-dienoyl-[glycerolipid],ferrocytochrome b5:oxygen oxidoreductase (15,16 cis-dehydrogenating)
This microsomal enzyme introduces a cis double bond three carbons away from the methyl end of a fatty acid incorporated into a glycerolipid. The distance from the carboxylic acid end of the molecule does not have an effect. The plant enzyme acts on carbon 15 of linoleoyl groups incorporated into both the sn-1 and sn-2 positions of the glycerol backbone of phosphatidylcholine and other phospholipids, converting them into alpha-linolenoyl groups. The enzyme from the fungus Mortierella alpina acts on gamma-linolenoyl and arachidonoyl groups, converting them into stearidonoyl and icosapentaenoyl groups, respectively [3]. cf. EC 1.14.19.35, acyl-lipid omega-3 desaturase (ferredoxin).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene fad3
UniProt
Manually annotated by BRENDA team
Brassica oleracea var. alboglabra
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
cv. SRl, gene fad3
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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accumulation of linoleoyl (18:2) groups at the expense of linolenoyl groups (18:3) is the only substantial difference in membrane lipid biosynthesis in leaves and roots of fad3-2 plants relative to wild type
metabolism
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
a dihomo-gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
a gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a stearidonoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
an arachidonoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
arachidonic acid + ferrocytochrome b5 + O2 + H+
eicosapentaenoic acid + ferricytochrome b5 + H2O
show the reaction diagram
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?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
omega-6 linoleic acid + ferrocytochrome b5 + O2 + H+
linolenic acid + ferricytochrome b5 + H2O
show the reaction diagram
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best substrate
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
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?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae
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expressed in Saccharomyces cerevisiae strain InvSc1
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expressed in Saccharomyces cerevisiae strain K601; expressed in Saccharomyces cerevisiae strain K601; expressed in Saccharomyces cerevisiae strain K601
expressed in Saccharomyces verevisiae strain InvSc1
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expression in Saccharomyces cerevisiae
gene fad3, DNA and amino acid sequence determination and analysis
gene fad3, recombinant expression of a fad3-LUC fusion construct in Arabidopsis thaliana plants through trabsfection with Agrobacterium tumefaciens strain C58 pGV3850
isolation of a gene and functionally complementation of a mutant of Arabidopsis deficient in omega-3 unsaturated fatty acids
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
auxin and cytokinin induce the enzyme expression ectopically in roots when applied during vegetative growth but not during repoductive growth or germination, the induction is repressed by abscisic acid
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
food industry
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combinations of mutations in the three FAD3 enzyme genes are capable of producing soybean seeds containing only 1% linolenic acid in the seed oil
additional information
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a mutant protein lacking 110 amino acids at its C terminus exhibits a drastic decline in its DELTA-15 desaturase activity compared to the wild type protein