Information on EC 1.14.19.6 - acyl-CoA (9+3)-desaturase

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

EC NUMBER
COMMENTARY hide
1.14.19.6
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RECOMMENDED NAME
GeneOntology No.
acyl-CoA (9+3)-desaturase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
oleoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = linoleoyl-CoA + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
(1)
-
-
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palmitoleoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = (9Z,12Z)-hexadeca-9,12-dienoyl-CoA + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
(2)
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-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of unsaturated fatty acids
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linoleate biosynthesis II (animals)
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sorgoleone biosynthesis
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arachidonate biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA,ferrocytochrome b5:oxygen oxidoreductase (12,13 cis-dehydrogenating)
This microsomal enzyme introduces a cis double bond at position 12 of fatty-acyl-CoAs that contain a cis double bond at position 9. When acting on 19:1Delta10 fatty acyl-CoA the enzyme from the pathogenic protozoan Trypanosoma brucei introduces the new double bond at position 13, indicating that the new double bond is introduced three carbons from the existing cis double bond, towards the methyl-end of the fatty acid. Requires cytochrome b5 as the electron donor [4].
CAS REGISTRY NUMBER
COMMENTARY hide
84628-81-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
female moth
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-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
strain TD#822-2, gene Cop-odeA; TD822-2
TrEMBL
Manually annotated by BRENDA team
strain TD#822-2, gene Cop-odeA
TrEMBL
Manually annotated by BRENDA team
TD822-2
TrEMBL
Manually annotated by BRENDA team
gene Cs-fad2
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain NK1
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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TrEMBL
Manually annotated by BRENDA team
CBS 1807
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-
Manually annotated by BRENDA team
CBS 1807
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-
Manually annotated by BRENDA team
cultivar Nipponbare
UniProt
Manually annotated by BRENDA team
PtFAD2; PtFAD6
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-
Manually annotated by BRENDA team
gene Pc-fad2
UniProt
Manually annotated by BRENDA team
sweet quandong
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-
Manually annotated by BRENDA team
functional expression of a DELTA12 fatty acid desaturase gene from Spinacia oleracea in transgenic Sus scrofa
SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
wild-type and 12 fatty acid desaturase mutant strains
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-
Manually annotated by BRENDA team
gene Ssd12
UniProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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
(10Z)-nonadec-10-enoic acid + reduced acceptor + O2
(10Z,13Z)-nonadeca-10,13-dienoic acid + acceptor + H2O
show the reaction diagram
(Z)-9-tetradecenoic acid + ?
tetradec-9,12-dienoic acid
show the reaction diagram
1-oleoyl-2-acyl-[glycerolipid] + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
1-linoleoyl-2-acyl-[glycerolipid] + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
5,8,11,14-eicosatetraenoyl-CoA + reduced acceptor + O2
5,8,11,14,17-eicosadecapentaenoyl-CoA + acceptor + H2O
show the reaction diagram
6,9,12-octadecatrienoyl-CoA + reduced acceptor + O2
6,9,12,15-octadecatetraenoyl-CoA + acceptor + H2O
show the reaction diagram
9,12-octadecadienoyl-CoA + reduced acceptor + O2
9,12,15-octadecatrienoyl-CoA + acceptor + H2O
show the reaction diagram
9-hexadecenoyl-CoA + reduced acceptor + O2
9,12-hexadecadienoyl-CoA + acceptor + H2O
show the reaction diagram
low activity
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-
?
9-octadecenoyl-CoA + reduced acceptor + O2
9,12-octadecadienoyl-CoA + acceptor + H2O
show the reaction diagram
-
-
-
?
acyl-CoA + reduced acceptor + O2
DELTA12-acyl-CoA + acceptor + H2O
show the reaction diagram
-
-
-
?
cis-7-hexadecenoic acid + reduced acceptor + O2
cis,cis-7,10-hexadecadienoic acid + acceptor + H2O
show the reaction diagram
-
5.2% desaturation
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-
?
cis-9-heptadecenoic acid + reduced acceptor + O2
cis,cis-9,12-heptadecadienoic acid + acceptor + H2O
show the reaction diagram
-
22.3% desaturation
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-
?
cis-9-hexadecenoic acid + reduced acceptor + O2
cis,cis-9,12-hexadecadienoic acid + acceptor + H2O
show the reaction diagram
cis-9-icosenoic acid + reduced acceptor + O2
cis,cis-11,14-icosadienoic acid + acceptor + H2O
show the reaction diagram
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4.1% desaturation
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-
?
cis-9-octadecenoic acid + reduced acceptor + O2
cis,cis-9,12-octadecadienoic acid + acceptor + 2 H2O
show the reaction diagram
eicosenoic acid + reduced acceptor + O2
20:2DELTA11,14 + acceptor + H2O
show the reaction diagram
62% conversion
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-
?
heptadecyloleic acid + reduced acceptor + O2
C17:2DELTA9,12 + acceptor + H2O
show the reaction diagram
-
-
-
?
myristoleic acid + reduced acceptor + O2
C14:2DELTA9,12 + acceptor + H2O
show the reaction diagram
-
-
-
?
oleic acid + ?
linoleic acid + ?
show the reaction diagram
oleic acid + reduced acceptor + O2
linoleic acid + acceptor + H2O
show the reaction diagram
oleic acid + reduced acceptor + O2
linoleic acid + alpha-linolenic acid + acceptor + H2O
show the reaction diagram
oleoyl-CoA + reduced acceptor + O2
9,12-octadecadienoyl-CoA + acceptor + 2 H2O
show the reaction diagram
oleoyl-CoA + reduced acceptor + O2
octadec-9,11-dienoyl-CoA + acceptor + 2 H2O
show the reaction diagram
palmitoleic acid + reduced acceptor + O2
(9Z,12Z)-hexadeca-9,12-dienoic acid + acceptor + H2O
show the reaction diagram
pentadecyloleic acid + reduced acceptor + O2
C15:2DELTA9,12 + acceptor + H2O + acceptor
show the reaction diagram
-
-
-
?
stearolic acid + reduced acceptor + O2
trans-12-octadecen-9-ynoic acid + acceptor + H2O
show the reaction diagram
additional information
?
-
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
(Z)-9-tetradecenoic acid + ?
tetradec-9,12-dienoic acid
show the reaction diagram
-
biosynthetic pathway for producing the sex pheromone component (Z,E)-9,12-tetradecadienyl acetate in moths involves a DELTA12 desaturase
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-
?
1-oleoyl-2-acyl-[glycerolipid] + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
1-linoleoyl-2-acyl-[glycerolipid] + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
cis-9-octadecenoic acid + reduced acceptor + O2
cis,cis-9,12-octadecadienoic acid + acceptor + 2 H2O
show the reaction diagram
-
PtFAD2 is involved in the biosynthesis of eicosapentaenoic acid
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-
?
eicosenoic acid + reduced acceptor + O2
20:2DELTA11,14 + acceptor + H2O
show the reaction diagram
A0A088MFF4
62% conversion
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?
oleic acid + ?
linoleic acid + ?
show the reaction diagram
oleic acid + reduced acceptor + O2
linoleic acid + acceptor + H2O
show the reaction diagram
oleoyl-CoA + reduced acceptor + O2
9,12-octadecadienoyl-CoA + acceptor + 2 H2O
show the reaction diagram
oleoyl-CoA + reduced acceptor + O2
octadec-9,11-dienoyl-CoA + acceptor + 2 H2O
show the reaction diagram
-
the DELTA12 desaturase provides the key step for the cockroach to become nutritionally independent of dietary lipid and to synthesize eicosanoids de novo
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?
palmitoleic acid + reduced acceptor + O2
(9Z,12Z)-hexadeca-9,12-dienoic acid + acceptor + H2O
show the reaction diagram
stearolic acid + reduced acceptor + O2
trans-12-octadecen-9-ynoic acid + acceptor + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
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Ferredoxin
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additional information
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does not contain cytochrome b 5
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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activation, DELTA12-desaturase system, enzymatic complex
Mn2+
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activation, DELTA12-desaturase system, enzymatic complex
Zn2+
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activation, DELTA12-desaturase system, enzymatic complex
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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DELTA12-desaturase system, enzymatic complex
Hg2+
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DELTA12-desaturase system, enzymatic complex
Iodine
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DELTA12-desaturase system, enzymatic complex
iodoacetic acid
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DELTA12-desaturase system, enzymatic complex
N-bromosuccinimide
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DELTA12-desaturase system, enzymatic complex
N-ethyl-5-phenylisoxazolium 3'-sulfonate
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DELTA12-desaturase system, enzymatic complex
NEM
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DELTA12-desaturase system, enzymatic complex
rifampicin
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trifluoroacetic acid
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DELTA12-desaturase system, enzymatic complex
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8
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DELTA12-desaturase system, enzymatic complex
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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assay at
40
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DELTA12-desaturase system, enzymatic complex
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
very low expression level in roots
Manually annotated by BRENDA team
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low activity
Manually annotated by BRENDA team
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most of the activity
Manually annotated by BRENDA team
4.2fold increase in mRNA level in mature fruiting bodies compared to mycelium
Manually annotated by BRENDA team
3.5fold increase in mRNA level in fruiting body primordia and 4.2fold increase in mRNA level in mature fruiting bodies compared to mycelium
Manually annotated by BRENDA team
3.5fold increase in mRNA level in fruiting body primordia compared to mycelium
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36000
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x * 36000, SDS-PAGE
40500
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x * 40500, DesA, SDS-PAGE, x * 66000, about, recombinant DesA-LicBM3 hybrid protein, SDS-PAGE
40700
x * 40700, calculated from amino acid sequence
51100
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x * 51100, FLAG-tagged enzyme, SDS-PAGE
66000
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x * 40500, DesA, SDS-PAGE, x * 66000, about, recombinant DesA-LicBM3 hybrid protein, SDS-PAGE; x * 66000, DesA As hybrid with lichenase LicBM3, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
soluble recombinant enzyme from Escherichia coli strains JM109 and BL21(DE3)
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, high level expression in Escherichia coli strains JM109 and BL21(DE3)
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expressed in Anacystis nidulans strain R2-SPc
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli strains XL1Blue and BL21 and Solanum tuberosum cells; gene desA, recombinant expression of the desA-licBM3 hybrid in transgenic Escherichia coli strains XL1Blue and BL21 and Solanum tuberosum plants
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expressed in Mus musculus strains C57BL/6 and DBA/2
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expressed in Nicotiana tabacum cultivar Wisconsin
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expressed in Saccharomyces cerevisiae
expressed in Saccharomyces cerevisiae and in Arabidopsis thaliana
expressed in Saccharomyces cerevisiae and in the Arabidopsis thaliana fad2-1 mutant (knockout mutants lacking the single FAD2 gene)
expressed in Saccharomyces cerevisiae EH1315, 7.9% oleic acid and 29% linoleic acid in yeast expressing DELTA12 desaturase compared with 37% oleic acid and no detectable linoleic acid in control yeast, fatty acid composition analyzed by gas-liquid chromatography; gene Cop-odeA, DNA and amino acid sequence determination and analysis, functional expression in Saccharomyces cerevisiae strain EH1315
expressed in Saccharomyces cerevisiae INVSc1 cells and Aurantiochytrium limacinum mh0186 cells
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expressed in Saccharomyces cerevisiae INVScI and Pichia pastoris GS115 cells
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expressed in Saccharomyces cerevisiae strain IFO10150
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expressed in Saccharomyces cerevisiae strain InvSc1
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expressed in Solanum lycopersicum cultivar Desnitsa
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expressed in Solanum tuberosum cultivar Desnitsa
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expressed in wild-type Yarrowia lipolytica and its DELTA12 desaturase knockout mutant, 62.6 weight percent of total fatty acid was linoleic acid produced in the mutant
expression in Saccharomyces cerevisiae
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expression in Saccharomyces cerevisiae leads to endogenous production of linoleic acid, the proportion of linoleic acid in the total fatty acids produced by transformed Saccharomyces cerevisiae increases from 1.1 mol% when grown at 30°C to 2.9 mol% when grown at 15°C
expression in Saccharomyces cerevisiae strain BYdesa
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expression in Saccharomyces cerevisiae strain YHU3046-4A results in endogenous production of linoleic acid, increasement in production of linoleic acid from 0.66 to 1.19 microg/mg dry cell weight when 0.5 microM oleic acid as a substrate was exogenously added
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expression of DELTA12-fatty acid desaturase genes in Escherichia coli strain BL21 and Saccharomyces cerevisiae strain IN-VSc1 leads to production of an active enzyme which converts 17.876% and 17.604% of oleic acid to linoleic acid, GC-MS detection in vitro and in vivo
functional expression of a DELTA12 fatty acid desaturase gene from Spinacia oleracea in transgenic Sus scrofa. Levels of linoleic acid (18:2n-6) in adipocytes that have differentiated in vitro from cells derived from the transgenic pigs are about 10times higher than those from wild-type pigs. In addition, the white adipose tissue of transgenic pigs contained about 20% more linoleic acid (18:2n-6) than that of wild-type pigs
gene An1, DNA and amino acid sequence determination and analysis, functional expression in Arabidopsis thaliana; gene An2, DNA and amino acid sequence determination and analysis, functional expression in Arabidopsis thaliana
gene Cs-fad2, DNA and amino acid sequence determination and analysis, transcriptional analysis, and functional expression in and complementation of enzyme-deficient Saccharomyces cerevisiae S288C mutant strain NBRC1136
gene FAD6, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, expression in Saccharomyces cerevisiae strain INVSc1, expression analysis; gene FAD6, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, expression in Saccharomyces cerevisiae strain INVSc1, expression analysis
gene Pc-fad2, DNA and amino acid sequence determination and analysis
gene Ssd12, DNA and amino acid sequence determination and analysis, two genomic copies, expression in Saccharomyces cerevisiae
heterologous expression in Saccharomyces cerevisiae and Aspergillus oryzae
heterologous expression in yeast Saccharomyces cerevisiae and Synechococcus
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression of FAD6 increases fourfold at 4°C compared to expression at 25°C. FAD6 transcription is sensitive to saline stress with a 20fold increase at 6% NaCl; expression of FAD6 increases fourfold at 4°C compared to expression at 25°C. FAD6 transcription is sensitive to saline stress with a 20fold increase at 6% NaCl
FAD2 mRNA accumulates in leaf mesophyll cells and in root epidermis cells when exposed to 15°C for 4 days in dark conditions
induction of FAD2 expression following a 24 h incubation at 10°C is light dependent, no difference in FAD2 expression is found in plants grown between 32°C and 20°C
mRNA accumulation shows a periodic behaviour, decreasing to the 22°C levels following a 48 h incubation and re-establishing ist 24 h induction after 96 h
no enhancement of enzyme transcript is observed when cells are incubated in the dark at 22°C
shifting of the Mucor rouxii culture from anaerobic to aerobic conditions upregulates levels of expressions of the DELTA9-, DELTA12- and DELTA6-desaturases genes, overview. The transcriptional response is rapid and transient, with the maximal mRNA levels between 0.5 h and 1.0 h after the shift
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the induction of FAD2 is inhibited by incubation at 10°C under dark conditions but appears unaffected by light intensity
the level of the enzyme transcript increases 10fold within 1 h upon a decrease in temperature from 36°C to 22°C
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H109R
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inactive
H129R
-
inactive
H287R
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inactive
H290R
-
inactive
H90R
-
inactive
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
after functional expression of a DELTA12 fatty acid desaturase gene from Spinacia oleracea in transgenic Sus scrofa levels of linoleic acid (18:2n-6) in adipocytes that have differentiated in vitro from cells derived from the transgenic pigs are about 10 times higher than those from wild-type pigs. In addition, the white adipose tissue of transgenic pigs contained about 20% more linoleic acid (18:2n-6) than that of wild-type pigs. These results demonstrate the functional expression of a plant gene for a fatty acid desaturase in mammals, opening up the possibility of modifying the fatty acid composition of products from domestic animals by transgenic technology, using plant genes for fatty acid desaturases