Information on EC 1.14.19.3 - acyl-CoA 6-desaturase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.19.3
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RECOMMENDED NAME
GeneOntology No.
acyl-CoA 6-desaturase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
alpha-linolenoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = stearidonoyl-CoA + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
(2)
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-
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linoleoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = gamma-linolenoyl-CoA + 2 ferricytochrome b5+ 2 H2O
show the reaction diagram
(1)
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate biosynthesis (6-desaturase)
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Biosynthesis of unsaturated fatty acids
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docosahexaenoate biosynthesis III (6-desaturase, mammals)
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gamma-linolenate biosynthesis II (animals)
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icosapentaenoate biosynthesis II (6-desaturase, mammals)
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Linoleic acid metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
linoleoyl-CoA,hydrogen-donor:oxygen oxidoreductase
An iron protein. The enzyme introduces a cis double bond at carbon 6 of acyl-CoAs. It is a front-end desaturase, introducing the new double bond between a pre-existing double bond and the carboxyl-end of the fatty acid. The human enzyme has a broad substrate range. It also acts on palmitoyl-CoA, generating sapienoyl-CoA [4], and on (9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoyl-CoA, converting it to (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoyl-CoA as part of a pathway that produces docosahexaenoate [3]. The enzyme contains a cytochrome b5 domain that is assumed to act in vivo as the electron donor to the active site of the desaturase.
CAS REGISTRY NUMBER
COMMENTARY hide
9014-34-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
Heynh
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Manually annotated by BRENDA team
Heynh
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Manually annotated by BRENDA team
gene fat-3
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Manually annotated by BRENDA team
strain MIAN6
UniProt
Manually annotated by BRENDA team
strain MIAN6
UniProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
soybean, cv Tracy
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Manually annotated by BRENDA team
linseed, cultivar Punjab
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Manually annotated by BRENDA team
gene PiDesD6
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
Muraenesox cinereus pike eel
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UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
gene ObD6Des
UniProt
Manually annotated by BRENDA team
; DELTA6-desaturase
SwissProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
strain Sprague-Dawley
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-
Manually annotated by BRENDA team
strain Wistar
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain As.3.2806
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Manually annotated by BRENDA team
strain As3.2806
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
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
24-carbon fatty acid + AH2 + O2
? + A + H2O
show the reaction diagram
alpha-linolenic acid + AH2 + O2
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid + A + H2O
show the reaction diagram
preferred substrate
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-
?
alpha-linolenic acid + AH2 + O2
?
show the reaction diagram
alpha-linolenic acid + AH2 + O2
octadec-6,9,12,15-tetraenoic acid + A + H2O
show the reaction diagram
alpha-linolenic acid + AH2 + O2
octadeca-6,9,12,15-tetraenoic acid + A + H2O
show the reaction diagram
-
-
-
?
alpha-linolenic acid + AH2 + O2
octadecatetraenoic acid + A + H2O
show the reaction diagram
-
-
-
-
?
alpha-linolenic acid + AH2 + O2
stearidonic acid + A + H2O
show the reaction diagram
alpha-linolenoyl-CoA + ferrocytochrome b5 + O2 + H+
stearidonoyl-CoA + ferricytochrome b5 + H2O
show the reaction diagram
alpha-linoleoyl-CoA + AH2 + O2
stearidonoyl-CoA + A + 2 H2O
show the reaction diagram
gamma-linoleic acid + AH2 + O2
gamma-linolenic acid + A + H2O
show the reaction diagram
-
39% conversion efficiency
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-
?
gamma-linolenic acid + AH2 + O2
cis-6,9,12,15-octadecatetraenoic acid + A + H2O
show the reaction diagram
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-
-
-
?
gamma-linolenic acid methyl ester + O2
?
show the reaction diagram
heptadec-9-enoic acid + AH2 + O2
heptadec-6,9-dienoic acid + A + H2O
show the reaction diagram
-
conversion rate is 17%
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-
?
linoleic acid + AH2 + O2
?
show the reaction diagram
linoleic acid + AH2 + O2
gamma-linoleic acid + A + H2O
show the reaction diagram
-
-
-
-
?
linoleic acid + AH2 + O2
gamma-linolenic acid + A + H2O
show the reaction diagram
linolenic acid + AH2 + O2
arachidonic acid + A + H2O
show the reaction diagram
linoleoyl phosphatidylcholine + AH2 + O2
gamma-linolenoylphosphatidylcholine + A + H2O
show the reaction diagram
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-
-
-
?
linoleoyl-CoA + AH2 + O2
gamma-linolenoyl-CoA + A + 2 H2O
show the reaction diagram
linoleoyl-CoA + ferrocytochrome b5 + O2 + H+
gamma-linolenoyl-CoA + ferricytochrome b5 + H2O
show the reaction diagram
monogalactosydiacylglycerol + AH2 + O2
? + A + H2O
show the reaction diagram
octadec-9,12-dienoic acid + AH2 + O2
octadec-6,9,12-trienoic acid + A + H2O
show the reaction diagram
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conversion rate is 11.5%
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?
octadec-9-enoic acid + AH2 + O2
octadec-6,9-dienoic acid + A + H2O
show the reaction diagram
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conversion rate is 19.1%
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?
octadeca-9,12-dienoic acid + AH2 + O2
gamma-linolenic acid + A + H2O
show the reaction diagram
octadecanoate + AH2 + O2
? + A + H2O
show the reaction diagram
oleic acid + AH2 + O2
?
show the reaction diagram
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?
palmitate + AH2 + O2
sapienate + A + H2O
show the reaction diagram
palmitic acid + AH2 + O2
hexadec-6-enoic acid + A + H2O
show the reaction diagram
palmitoyl-[acyl-carrier protein] + reduced acceptor + O2
6-hexadecenoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
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-
?
stearoyl-[acyl-carrier protein] + reduced acceptor + O2
6-octadecenoyl-[acyl-carrier protein] + 9-octadecenoyl-[acyl-carrier protein]acceptor + H2O
show the reaction diagram
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ratio of activity: 2/1
?
tetracosapentaenoic acid + AH2 + O2
tetracosahexaenoic acid + A + H2O
show the reaction diagram
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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
alpha-linolenic acid + AH2 + O2
octadec-6,9,12,15-tetraenoic acid + A + H2O
show the reaction diagram
alpha-linolenoyl-CoA + ferrocytochrome b5 + O2 + H+
stearidonoyl-CoA + ferricytochrome b5 + H2O
show the reaction diagram
alpha-linoleoyl-CoA + AH2 + O2
stearidonoyl-CoA + A + 2 H2O
show the reaction diagram
E1U2Q3
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-
?
linoleic acid + AH2 + O2
gamma-linolenic acid + A + H2O
show the reaction diagram
linoleoyl-CoA + AH2 + O2
gamma-linolenoyl-CoA + A + 2 H2O
show the reaction diagram
E1U2Q3
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-
?
linoleoyl-CoA + ferrocytochrome b5 + O2 + H+
gamma-linolenoyl-CoA + ferricytochrome b5 + H2O
show the reaction diagram
palmitate + AH2 + O2
sapienate + A + H2O
show the reaction diagram
O95864
the enzyme is a component of the lipid metabolic pathway that converts the essential fatty acids linoleate and alpha-linolenate into long-chain polyunsaturated fatty acids. The DELTA-6 desaturase/FADS2 expressed in human sebocytes catalyzes the conversion of palmitate into sapienate
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?
palmitic acid + AH2 + O2
hexadec-6-enoic acid + A + H2O
show the reaction diagram
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key enzyme required for numerous vital functions involving distinct polyunsaturated fatty acids and polyunsaturated fatty acid-derived bioactive lipids. It seems that the biological importance of DELTA6-desaturase activity should also be considered for its newly identified role in the control of the biosynthesis of a monoenoic fatty acid (C16:1 n-10), particularly in tissues with low DELTA9-desaturase activity
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
Ferredoxin
heme
contains a cytochrome b5 heme-binding domain
linoleoyl-CoA
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absolutely essential for DELTA6-desaturation
NADH
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absolutely essential for DELTA6-desaturation
NADPH
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absolutely essential for DELTA6-desaturation
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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DELTA6-desaturase contains 15.1 nmol iron/mg protein
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-chloro-5-dimethylamino-2-phenyl-3(2H)-pyridazinone
bathophenanthroline sulfonate
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mild inhibition
beta-mercaptoethanol
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mild inhibition
cholesterol
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conjugated linoleic acid
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all CLA isomers inhibits significantly the activity of DELTA6-desaturase, the c9,t11 isomer is the most potent inhibitor
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dithiothreitol
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mild inhibition
Iron chelators
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N-ethylmaleimide
p-chloromercuribenzene sulfonate
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saturated fatty acids
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trans-fats
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
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1-10 mg/ml, stimulates enzyme activity of unwashed microsomes by 50%
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catalase
NADH-cytochrome b5 reductase
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EC 1.6.2.2, absolutely essential for DELTA6-desaturation
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NADPH-cytochrome b5 reductase
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EC 1.6.2.2, absolutely essential for DELTA6-desaturation
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O2
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absolutely essential for DELTA6-desaturation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045
linoleoyl-CoA
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.1
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substrate palmitoyl-[acyl-carrier protein]
additional information
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0.3 mM exogenously added NADPH to Escherichia coli cells co-expressing DELTA6 desaturase and cytochrome b5 leads to an increase of the level of gamma-linoleic acid product by 50%, but no effect in Escherichia coli co-expressing DELTA6 desaturase and ferredoxin under the same conditions; co-addition of NADPH and FAD to Escherichia coli cells co-expressing DELTA6 desaturase and ferredoxin leads to an increase of the level of gamma-linoleic acid product; no activity when expressed in Escherichia coli alone, co-expression of cytochrome b5 is needed
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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expression is higher in salmon fed a diet containing vegetable oil than in fish fed a diet containing fish oil
Manually annotated by BRENDA team
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skin fibroblast
Manually annotated by BRENDA team
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much lower activity than in Sertoli cells
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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treatment with myristic acid specifically increases DELTA6-desaturase activity
Manually annotated by BRENDA team
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high expression, expression is higher in salmon fed a diet containing vegetable oil than in fish fed a diet containing fish oil
Manually annotated by BRENDA team
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mRNA level is upregulated by dexamethasone, follicle-stimulating hormone or cAMP
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
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recombinant DELTA6-desaturase expressed in COS-7 cells, analysed by Western blot
47000
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Western Blot, detection of histidine-tagged DELTA6 desaturase expressed in Escherichia coli using a monoclonal antibody against the histidine-tag
52000
calculated from amino acid sequence
52410
calculated from amino acid sequence
65000 - 68000
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gel filtration
66000
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SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phospholipoprotein
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, stored under nitrogen the enzyme is unstable, loses 80% of its activity after repeated freezing and thawing
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15°C, full-length enzyme in 100 mM sodium phosphate, pH 7.0, 4 h, 16% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
D6D, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis; D6D-V, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
DELTA6-desaturase gene identified in human chromosome 11
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DELTA6-desaturase II cDNA expressed in Aspergillus oryzae
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, functional expression in Saccharomyces cerevisiae strain INVSc1
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expressed in Camelina sativa
expressed in Escherichia coli DH5alpha, co-expressed with cytochrome b5 and ferredoxin, no enzyme activity when expressed in Escherichia coli alone
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expressed in HEK-293 cells
expressed in Pichia pastoris GS115; phylogenetic tree, expression in Pichia pastoris GS115, molecular mechanisms underlying the elevated expression of fatty acid desaturases induced by a decrease in the environmental temperature
expressed in Pichia pastoris strain GS115
expressed in Saccharomyces cerevisiae
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expressed in Saccharomyces cerevisiae strain BY4741, two different mRNA variants
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expressed in Saccharomyces cerevisiae strain InvSc1
expressed in Saccharomyces cerevisiae strain InvSc1; expression in Saccharomyces cerevisiae
expressed in Saccharomyces cerevisiae strain INVScl
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expressed in Saccharomyces cerevisiae, strain DBY746 with and without supplementation with linoleic acid
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expression in Saccharomyces cerevisaiae
expression in Saccharomyces cerevisiae
expression of N-terminal truncated enzyme in Escherichia coli
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expression of wild-type, A181T/A188G/Y189F/S205N/L206T/G207A, A188G/Y189F, A181T/A200F and A181T/A200F/S205N/L206T/G207A mutant enzyme in Escherichia coli
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gene DELTA6fad_a, several variants, genetic structure, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression in Saccharomyces cerevisiae; gene DELTA6fad_b, several variants, genetic structure, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression in Saccharomyces cerevisiae; gene DELTA6fad_c, several variants, genetic structure, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression in Saccharomyces cerevisiae
gene desD, functional analysis of the Spirulina promoter in Escherichia coli, the -10 sequence, TATAAT, located at -33 bp relative to the translation start site, is essential for D6D promoter function, an ‘AT-rich inverted repeat’ -192 to -164 serves as a target-binding site for a transcriptional regulator
gene fat-3, quantitative real-time PCR expression analysis, overview
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gene ObD6Des, DNA and amino acid sequence determination and analysis, sequence comparisons, functional expression in Saccharomyces cerevisiae strain W303-a
gene PiDesD6, DNA and amino acid sequence determination and analysis, phylogenetic analysis, functional expression in Saccharomyces cerevisiae strain W303, real-time quantitative PCR expression analysis
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human sequence determined
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plasmid coding for rat delta6-desaturase constructed using pCMV for expression in mammalian cells, rat delta6-desaturase sequence, GenBank accession number AB02 1980 PCR amplified, expressed by transiently transforming COS-7 cells
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RT-PCR analysis of INS-1 beta-cell content of mRNA, primer pairs basedon known rat sequence
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Saccharomyces cerevisiae transformed with fungal DELTA6-desaturase gene
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transformed into Agrobacterium tumefaciens and expressed in Glycine max
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H129G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity, can be rescued by 150 mM exogenous imidazole
H129R
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity using linoleic acid as substrate
H305G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity, can be rescued by 150 mM exogenous imidazole
H305R
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity using linoleic acid as substrate
H89G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, very low enzyme activity, can be rescued by 150 mM exogenous imidazole
H89R
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, very low enzyme activity using linoleic acid as substrate
H129G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity, can be rescued by 150 mM exogenous imidazole
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H129R
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity using linoleic acid as substrate
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H305G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, no enzyme activity, can be rescued by 150 mM exogenous imidazole
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H89G
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, very low enzyme activity, can be rescued by 150 mM exogenous imidazole
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H89R
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expressed in Saccharomyces cerevisiae, grown in SD medium in the presence of 50 microM of linoleic acid substrate, very low enzyme activity using linoleic acid as substrate
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G390D
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amino acid replacement in isoenzyme DELTA6I of DELTA6 desaturase-defective mutant strain YB214
T375K
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amino acid replacement in isoenzyme DELTA6I of DELTA6 desaturase-defective mutant strain HR95
W314Stop
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amino acid replacement in isoenzyme DELTA6I of DELTA6 desaturase-defective mutant strain ST66
A181T/A188G/Y189F/S205N/L206T/G207A
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compared to wild-type: reduced DELTA6 desaturase activity with palmitoyl-[acyl-carrier protein] as substrate, strong DELTA9 desaturase activity with stearoyl-[acyl-carrier protein] as substrate, exhibits DELTA9 desaturase activity with palmitoyl-[acyl-carrier protein] as substrate
A181T/A200F
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increase in DELTA6 desaturase activity with palmitoyl-[acyl-carrier protein] as substrate, strong DELTA9 desaturase activity with stearoyl-[acyl-carrier protein] as substrate
A181T/A200F/S205N/L206T/G207A
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reduced DELTA6 desaturase activity with palmitoyl-[acyl-carrier protein] as substrate, very low DELTA9 desaturase activity, no DELTA6 desaturase activity with stearoyl-[acyl-carrier protein] as substrate
A188G/Y189F
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reduced DELTA6 desaturase activity with palmitoyl-[acyl-carrier protein] as substrate
additional information
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genetic polymorphism of DELTA6 desaturase are naturally occuring in humans, a delivery of the gene for D6 desaturase to endothelial cells at atherosclerosis prone areas is expected to prevent/arrest the development of atherosclerosis despite the presence of hyperlipidemia, hypertension, diabetes mellitus, and at sites of shear stress of blood flow
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
the enzyme is a biological target for the discovery and development of pharmaceuticals to treat atherosclerosis
synthesis
Show AA Sequence (223 entries)
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