Information on EC 1.14.19.2 - stearoyl-[acyl-carrier-protein] 9-desaturase

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

EC NUMBER
COMMENTARY hide
1.14.19.2
-
RECOMMENDED NAME
GeneOntology No.
stearoyl-[acyl-carrier-protein] 9-desaturase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
stearoyl-[acyl-carrier protein] + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+ = oleoyl-[acyl-carrier protein] + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonate biosynthesis
-
-
Biosynthesis of unsaturated fatty acids
-
-
Fatty acid biosynthesis
-
-
oleate biosynthesis I (plants)
-
-
palmitoleate biosynthesis II (plants and bacteria)
-
-
SYSTEMATIC NAME
IUBMB Comments
stearoyl-[acyl-carrier protein],reduced ferredoxin:oxygen oxidoreductase (9,10 cis-dehydrogenating)
The enzyme is found in the lumen of plastids, where de novo biosynthesis of fatty acids occurs, and acts on freshly synthesized saturated fatty acids that are still linked to acyl-carrier protein. The enzyme determines the position of the double bond by its distance from the carboxylic acid end of the fatty acid. It also acts on palmitoyl-[acyl-carrier-protein] [4,5].
CAS REGISTRY NUMBER
COMMENTARY hide
37256-86-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
milkweed
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Bignonia unguis-cati
cat's claw
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
coriander
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
H37Rv, variants DesA1
SwissProt
Manually annotated by BRENDA team
Mycobacterium tuberculosis H37Rv,variant DesA2
H37Rv,variant DesA2
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
avocado
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
the enzyme catalyzes the conversion of stearic acid (18:0) to oleic acid (18:1) in fatty acid biosynthesis. Enzyme overexpression enhances the synthesis of oleic acid 2.4fold
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
10-(heptyloxy)-decanoyl-[acyl-carrier protein] + reduced acceptor + O2
9-hydroxynonanoyl-[acyl-carrier protein] + n-octanal + acceptor + H2O
show the reaction diagram
-
-
-
?
7-(decyloxy)-heptanoyl-[acyl-carrier protein] + reduced acceptor + O2
7-dec-1-enyloxyheptanoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
-
-
-
?
8-(nonyloxy)-octanoyl-[acyl-carrier protein] + reduced acceptor + O2
8-hydroxyoctanoyl-[acyl-carrier protein] + 1-nonanal + acceptor + H2O
show the reaction diagram
-
-
-
?
9-(octyloxy)-nonanoyl-[acyl-carrier protein] + reduced acceptor + O2
9-hydroxynonanoyl-[acyl-carrier protein] + 1-octanal + acceptor + H2O
show the reaction diagram
-
-
-
?
heptadecanoyl-[acyl-carrier protein] + reduced ferredoxin + O2
9-heptadecenoyl-[acyl-carrier protein] + oxidized ferredoxin + H2O
show the reaction diagram
-
very low activity, vegetative ferredoxin from Anabaena
-
?
nonadecanoyl-[acyl-carrier protein] + reduced ferredoxin + O2
9-nonadecenoyl-[acyl-carrier protein] + oxidized ferredoxin + H2O
show the reaction diagram
-
low activity, vegetative ferredoxin from Anabaena
-
?
palmitoyl-[acyl-carrier protein] + AH2 + O2
palmitoleoyl-[acyl-carrier protein] + A + H2O
show the reaction diagram
palmitoyl-[acyl-carrier protein] + reduced acceptor + O2
9-hexadecenoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
pentadecanoyl-[acyl-carrier protein] + reduced ferredoxin + O2
9-pentadecenoyl-[acyl-carrier protein] + oxidized ferredoxin + H2O
show the reaction diagram
-
very low activity, vegetative ferredoxin from Anabaena
-
?
stearoyl-CoA + electron donor + O2
9-octadecenoyl-CoA + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + electron donor + O2
oleoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + electron donor + O2
oleoyl-[acyl-carrier protein] + electron acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + ferredoxin + O2
oleoyl-[acyl-carrier protein] + oxidized ferredoxin + H2O
show the reaction diagram
-
-
-
?
stearoyl-[acyl-carrier protein] + reduced acceptor + O2
9-octadecenoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + reduced acceptor + O2
oleoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + reduced ferredoxin [iron-sulfur] cluster + O2 + H(+)
oleoyl-[acyl-carrier protein] + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-
-
-
-
?
stearoyl-[acyl-carrier-protein] + reduced acceptor + O2
oleoyl-[acyl-carrier-protein] + acceptor + H2O
show the reaction diagram
tetradecanoyl-[acyl-carrier protein] + reduced acceptor + O2
9-tetradecenoyl-[acyl-carrier protein] + 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
stearoyl-[acyl-carrier protein] + electron donor + O2
oleoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + electron donor + O2
oleoyl-[acyl-carrier protein] + electron acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + ferredoxin + O2
oleoyl-[acyl-carrier protein] + oxidized ferredoxin + H2O
show the reaction diagram
Q4JIJ4
-
-
-
?
stearoyl-[acyl-carrier protein] + reduced acceptor + O2
oleoyl-[acyl-carrier protein] + acceptor + H2O
show the reaction diagram
stearoyl-[acyl-carrier protein] + reduced ferredoxin [iron-sulfur] cluster + O2 + H(+)
oleoyl-[acyl-carrier protein] + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-
-
-
-
?
stearoyl-[acyl-carrier-protein] + reduced acceptor + O2
oleoyl-[acyl-carrier-protein] + acceptor + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ferredoxin
additional information
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
beta-mercaptoethanol
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cytochrome c3
-
-
cytochrome c553
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
catalase
dithiothreitol
enhances activity
reduced glutathione
enhances activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0074
10-(heptyloxy)-decanoyl-[acyl-carrier protein]
-
-
0.0066
7-(decyloxy)-heptanoyl-[acyl-carrier protein]
-
-
0.0059
heptadecanoyl-[acyl-carrier protein]
-
-
0.00055 - 0.0083
hexadecanoyl-[acyl-carrier protein]
0.0013
nonadecanoyl-[acyl-carrier protein]
-
-
0.00046 - 0.0039
octadecanoyl-[acyl-carrier protein]
0.00051
palmitoyl-[acyl-carrier protein]
-
-
0.069
pentadecanoyl-[acyl-carrier protein]
-
-
0.0083
stearoyl-CoA
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-
0.00038
stearoyl-[acyl-carrier protein]
-
-
0.001 - 0.0058
tetradecanoyl-[acyl-carrier protein]
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.5
10-(heptyloxy)-decanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.2
7-(decyloxy)-heptanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.04
8-(nonyloxy)-octanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.02
9-(octyloxy)-nonanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.233
heptadecanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.0467 - 0.422
hexadecanoyl-[acyl-carrier protein]
0.2
nonadecanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.0817 - 0.817
octadecanoyl-[acyl-carrier protein]
0.0317
pentadecanoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.333 - 0.5
stearoyl-[acyl-carrier protein]
Ricinus communis
-
-
0.0065 - 0.817
tetradecanoyl-[acyl-carrier protein]
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000016
activity in extracts from Escherichia coli M15 transformed with pQESAD, uninduced, with reduced spinach ferredoxin
0.000002
activity in extracts from Escherichia coli M15 transformed with pQESAD, uninduced, without reduced spinach ferredoxin
0.000003
His-tag fusion protein overexpressed in Escherichia coli M15 without ferredoxin, without IPTG-induction
0.0000075
activity in extracts from Escherichia coli M15 transformed with pQESAD, induced, with reduced spinach ferredoxin
0.000079
activity in extracts from Escherichia coli M15 transformed with pQESAD, induced, without reduced spinach ferredoxin
0.000082
His-tag fusion protein overexpressed in Escherichia coli M15 without ferredoxin, IPTG-induced
0.00157
His-tag fusion protein overexpressed in Escherichia coli M15 with exogenous spinach ferredoxin, without IPTG-induction
0.00795
His-tag fusion protein overexpressed in Escherichia coli M15 with exogenous spinach ferredoxin, without IPTG-induced
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 7.7
-
pH 5.5: about 50% activity, pH 7.7: about 50% activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.4
calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highly expressed in developing fruits
Manually annotated by BRENDA team
-
flax ovary, RT-PCR
Manually annotated by BRENDA team
RT-PCR, gene-specific primers for the isoform; RT-PCR, gene-specific primers for the isoform; RT-PCR, gene-specific primers for the isoform; RT-PCR, gene-specific primers for the isoform; RT-PCR, gene-specific primers for the isoform; RT-PCR, gene-specific primers for the isoform
Manually annotated by BRENDA team
additional information
-
bolls at different developmental stages, RT-PCR
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43000
SDS-PAGE, overexpressed His-tag fusion protein
43500
recombinant 6 x His-SAD, determined by SDS-PAGE
44180
calculated from amino acid sequence
45020
calculated from amino acid sequence
45290
calculated from amino acid sequence
45480
calculated from amino acid sequence
45510
precursor
45690
calculated from amino acid sequence
45860
calculated from amino acid sequence
46950
calculated from amino acid sequence
50500
-
determined by SDS-PAGE
68000
-
gel filtration
75000
-
recombinant enzyme lacking a putative transit peptide
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DesA2 crystals grown by the method of hanging drop vapor diffusion, one metal bound per subunit which is likely Mn2+, native and selenomethionine-substituted, 2.0 A resolution X-ray structure
hanging drop vapor diffusion, 12-18 mg/ml enzyme solution, reservoir solution contains 100 mM cacodylate buffer, pH 5.4, 200 mM magnesium acetate and 12-18% polyethyleneglycol 8000, needle shaped crystals too thin for X-ray study
-
in complex with azide or acetae, apo- and single-iron form
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
-
1 min, inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
unstable to dialysis
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, 50% glycerol, 0.1% bovine serum albumin, 100 mM potassium phosphate buffer, pH 6.8, at least 2 months, no loss of activity
-
0°C, 10 h, 50% loss of activity
-
4°C, overnight, 30% loss of activity
-
frozen state, 1 month, complete loss of activity
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
aceton powder, anion-exchange, affinity chromatography on acyl-carrier protein-Sepharose
-
by Ni-NTA purification system
-
DesA2 isoform purified by ion exchange and gel filtration chromatographies
overexpressed S-ACP-DES1 enzyme; overexpressed S-ACP-DES3 enzyme; overexpressed S-ACP-DES4 enzyme; overexpressed S-ACP-DES5 enzyme
recombinant enzyme
recombinant enzyme lacking a putative transit peptide
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a Brassica napus bacterial artificial chromosome, BAC, library is constructed
-
cloned in pQE-30 vector and expressed in Escherichia coli strain M15, His-tag
cloning of isoform 1; cloning of isoform 2
DesA1 overexpressed in Escherichia coli BL21-(DE3) with the natural N-terminal methionine residue as the first amino acid; DesA2 overexpressed in Escherichia coli BL21-(DE3) with the natural N-terminal methionine residue as the first amino acid
expressed in Escherichia coli BL21 Star (DE3) cells
-
expressed in Escherichia coli BL21(DE3) cells
expression in Escherichia coli
expression of 2 isoforms in Escherichia coli
-
expression of cDNA in Escherichia coli
full-length cDNA clone
-
into the pUCm-T vector and subcloned into the vector pET30a for expression in Escherichia coli BL21DE3 cells
-
into the vector pQE-30 for expression in Escherichia coli M15 cells
OeSAD2 is not expressed as a soluble protein
-
S-ACP-DES1 expressed in Escherichia coli; S-ACP-DES3 enzyme expressed in Escherichia coli; S-ACP-DES4 enzyme expressed in Escherichia coli; S-ACP-DES5 enzyme expressed in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
12-24 h after cold stress the enzyme expression is strongly increased and decreases thereafter
ahSAD3 is expressed exclusively during seed development
-
exposure to HL (0.4 mM photons m-2 s-1) significantly increases the enzyme's mRNA level. Nitrogen deficiency also markedly up-regulates the expression of the enzyme. mRNA levels of the enzyme are drastically upregulated, reaching their maximum at 48 h after glucose induction
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L118F/P179I
-
15fold higher activity with palmitoyl-[acyl-carrier protein] than wild-type enzyme, low DELTA10 desaturase activity
L118W
-
100% activity with palmitoyl-[acyl-carrier protein], 89% activity with stearoyl-[acyl-carrier protein] and 8.2% activity with myristoyl-[acyl-carrier protein], wild-type is only active with stearoyl-[acyl-carrier protein]
T117R/G188L
-
82fold higher specificity for palmitoyl-[acyl-carrier protein] with respect to wild-type
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
-
mutant strain showing contents of up to 20% of unusual acyl chains such as 16:1DELTA9, 16:2DDELTA9,12, 18:1DELTA11, increase of enzyme activity in mutant
biofuel production
-
biodiesel production
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