Information on EC 1.14.19.5 - acyl-CoA 11-(Z)-desaturase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.19.5
-
RECOMMENDED NAME
GeneOntology No.
acyl-CoA 11-(Z)-desaturase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + reduced acceptor + O2 = Delta11-acyl-CoA + acceptor + 2 H2O
show the reaction diagram
an acyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = an (11Z)-enoyl-CoA + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
bombykol biosynthesis
-
-
Spodoptera littoralis pheromone biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
acyl-CoA,ferrocytochrome b5:oxygen oxidoreductase (11,12 cis-dehydrogenating)
The enzyme introduces a cis double bond at position C-11 of saturated fatty acyl-CoAs. In moths the enzyme participates in the biosynthesis of their sex pheromones. The enzyme from the marine microalga Thalassiosira pseudonana is specific for palmitoyl-CoA (16:0) [4], that from the leafroller moth Choristoneura rosaceana desaturates myristoyl-CoA (14:0) [5], while that from the moth Spodoptera littoralis accepts both substrates [1]. The enzyme contains three histidine boxes that are conserved in all desaturases [2]. It is membrane-bound, and contains a cytochrome b5-like domain at the N-terminus that serves as the electron donor for the active site of the desaturase.
CAS REGISTRY NUMBER
COMMENTARY hide
199543-17-4
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77000-04-5
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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functional expression of Dpu-DELTA11-APSQ cDNA belonging to the D11-subfamily, shows that is catalyses the formation of unsaturated fatty acyls that can be chain-shortened by beta-oxidation and subsequently reduced to the alcohol components; functional expression of Dpu-DELTA11-LPAE cDNA belonging to the D11-subfamily, shows that is catalyses the formation of unsaturated fatty acyls that can be chain-shortened by beta-oxidation and subsequently reduced to the alcohol components
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
(Z)-11-tetradecenoyl-CoA + reduced acceptor + O2
(E,E)-10,12-tetradecadienoyl-CoA + acceptor + H2O
show the reaction diagram
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(E,E)-10,12-tetradecadienoic acid is produced from (Z)-11-tetradecenoic acid by desaturation and concomitant migration of the precursor double bond
-
-
?
methyl myristate + reduced electron acceptor + O2
methyl (11E)-tetradec-11-enoate + methyl (11Z)-tetradec-11-enoate + acceptor + H2O
show the reaction diagram
myristic acid + NADH + ?
tetradec-11-enoic acid + NAD+ + ?
show the reaction diagram
-
50% of the activity with palmitic acid
-
-
?
myristic acid + reduced acceptor + O2
(Z)-tetradec-11-enoic acid + (E)-tetradec-11-enoic acid + acceptor + H2O
show the reaction diagram
-
-
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
show the reaction diagram
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + H2O
show the reaction diagram
myristoyl-CoA + reduced acceptor + O2
(Z)-tridec-11-enoyl-CoA + (E)-tridec-11-enoyl-CoA + acceptor + H2O
show the reaction diagram
-
reaction involves a first slow, isotpe-sensitive C11-H bond cleavage, with probable formation of an unstable intermediate, followed by a second fast C12-H bond removal
-
-
?
palmitic acid + NADH + ?
(Z)-hexadec-11-enoic acid + NAD+ + ?
show the reaction diagram
-
-
-
-
?
palmitic acid + reduced acceptor + O2
(Z)-11-hexadecenoic acid + acceptor + H2O
show the reaction diagram
-
-
-
-
?
palmitic acid + reduced acceptor + O2
(Z)-hexadec-11-enoic acid + acceptor + H2O
show the reaction diagram
palmitic acid + reduced acceptor + O2
hexadec-11-enoic acid + acceptor + 2 H2O
show the reaction diagram
palmitoyl-CoA + NADH + ?
(Z)-hexadec-11-enoyl-CoA + NAD+ + ?
show the reaction diagram
-
-
-
-
?
stearic acid + NADH + ?
oleic acid + NAD+ + ?
show the reaction diagram
-
18% of the activity with palmitic acid
-
-
?
stearoyl-CoA + reduced acceptor + O2
oleoyl-CoA + acceptor + 2 H2O
show the reaction diagram
-
-
-
?
tetradecanoic acid + O2 + AH2
(11E)-tetradec-11-enoic acid + A + 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
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
show the reaction diagram
palmitic acid + reduced acceptor + O2
hexadec-11-enoic acid + acceptor + 2 H2O
show the reaction diagram
Q6RT18
enzyme is not involved in production of polyunsaturated fatty acids
-
-
?
stearoyl-CoA + reduced acceptor + O2
oleoyl-CoA + acceptor + 2 H2O
show the reaction diagram
O44390
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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NADPH is a less effective elctron donor. Highest activity with 1 mM of electron donors, reduced activity below
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
11-fluorotetradecanoic acid
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50% inhibition at 1:1 substrate/inhibitor ratio
KCN
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83% inhibition by 1 mM, 95% inhibition by 5 mM
NaN3
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92% inhibition b
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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terminal abdominal segments with pheromone gland of female adults, RT-PCR
Manually annotated by BRENDA team
additional information
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in intersegmental membrane, 8th - 9th, in-situ hybridization; not in head, thorax, abdomen exclusive of the terminal abdominal segments
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37800
-
calculated from cDNA
39000
x * 39000, His-tagged enzyme, SDS-PAGE
40500
x * 40500, calculated from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 39000, His-tagged enzyme, SDS-PAGE; x * 40500, calculated from amino acid sequence
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, stable for at least 1 h
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C-terminal His-tagged fusion protein expressed using recombinant baculoviruses
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expressed as polyhistidine-tagged protein in elongase 1 and DELTA9 desaturase-deficient yeast cells; expression in Saccharomyces cerevisiae DELTAelo1/DELTAole mutant strain, which is both elongase 1 and DELTA9 desaturase-deficient, using a Cu+2 inducible expression vector, the recombinant expression leads to producing large quantities of C11-monounsaturated fatty acids, mainly (Z)-11-hexadecenoic acid, (E,E)-10,12-tetradecadienoic acid, minor amounts of (E,Z)-10,12-hexadecadienoic acid, and very low amounts of (E,Z)-10,12-tetradecadienoic isomer
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expressed in Sf9 insect cells
expressed in yeast
expression in yeast
gene d2, DNA and amino acid sequence determination and analysis, phylogenetic analysis, functional expression of MsexAPTQ desaturase in Saccharomyces cerevisiae strain W303
genetic trans-formation of a desaturase-deficient strain of the yeast Sac-charomyces cerevisiae with an expression plasmid encoding PDesat-Tn DELTA11Z results in complementation of the strain's fatty acid auxotrophy and the production of DELTA11 Z-unsaturated fatty acids
heterologously expressed in Saccharomyces cerevisiae
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into a copper-inducible pYEX vector to assess its desaturase activity and then transformed into a desaturase- and elongase-deficient mutant ole1 elo1 yeast strain
partial cDNAs are amplified and cloned into the vector pCold I DNA, recombinant proteins are produced by Escherichia coli BL21 cells and used as antigens to raise antibodies in mice