Information on EC 1.2.1.42 - hexadecanal dehydrogenase (acylating)

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

EC NUMBER
COMMENTARY hide
1.2.1.42
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RECOMMENDED NAME
GeneOntology No.
hexadecanal dehydrogenase (acylating)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
hexadecanal + CoA + NAD+ = hexadecanoyl-CoA + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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-
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
hexadecanal:NAD+ oxidoreductase (CoA-acylating)
Also acts, more slowly, on octadecanoyl-CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
72561-01-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
sp. strain M-1
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Manually annotated by BRENDA team
strain BD413
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Manually annotated by BRENDA team
strain BD413
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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-
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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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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
barn owl
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-methyl-1-hexadecanoyl-CoA + NADPH + H+
2-methyl-1-hexadecanal + CoA + NADP+
show the reaction diagram
arachidonoyl-CoA + NADPH + H+
arachidonic aldehyde + CoA + NADP+
show the reaction diagram
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86% activity compared to hexadecanoyl-CoA
-
-
?
cis-11-hexadecenal + CoA + NADP+
(E)-hexadec-11-enoyl-CoA + NADPh + H+
show the reaction diagram
-
-
-
-
?
decanoyl-CoA + NAD(P)H
decanal + NAD(P)+
show the reaction diagram
-
2.5% of activity with tetradecanoyl-CoA
-
?
docosanoyl-CoA + NADPH
docosanal + NADP+
show the reaction diagram
dodecanoyl-CoA + NAD(P)H
dodecanal + NAD(P)+
show the reaction diagram
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33% of activity with tetradecanoyl-CoA
-
?
dodecanoyl-CoA + NADPH + H+
dodecanal + CoA + NADP+
show the reaction diagram
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26% activity compared to hexadecanoyl-CoA
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-
?
eicosanoyl-CoA + NAD(P)H
eicosanal + NAD(P)+
show the reaction diagram
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2.5% of activity with tetradecanoyl-CoA
-
?
eicosanoyl-CoA + NADPH
eicosanal + NADP+
show the reaction diagram
heptadecanoyl-CoA + NADPH + H+
heptadecanal + CoA + NADP+
show the reaction diagram
-
-
-
-
?
hexadecanoyl-CoA + NAD(P)H
hexadecanal + NAD(P)+
show the reaction diagram
hexadecanoyl-CoA + NADH
hexadecanal + NAD+ + CoA
show the reaction diagram
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reduction of NAD+ is at most 5% of the rate of NADH oxidoreduction, the enzyme is primarily a reductase and not an aldehyde dehydrogenase
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?
hexadecanoyl-CoA + NADPH
hexadecanal + CoA + NADP+
show the reaction diagram
highest activity
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-
?
hexadecanoyl-CoA + NADPH
hexadecanal + NADP+
show the reaction diagram
hexadecanoyl-CoA + NADPH + H+
1-hexadecanal + CoA + NADP+
show the reaction diagram
hexadecanoyl-CoA + NADPH + H+
hexadecanal + CoA + NADP+
show the reaction diagram
octadecanoyl-CoA + NAD(P)H
octadecanal + NAD(P)+
show the reaction diagram
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44% of activity with tetradecanoyl-CoA
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?
octadecanoyl-CoA + NADH
octadecanal + NAD+ + CoA
show the reaction diagram
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slowly, octadecanoyl-CoA is identical with stearoyl-CoA
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-
?
octadecanoyl-CoA + NADPH
octadecanal + CoA + NADP+
show the reaction diagram
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-
-
?
octadecanoyl-CoA + NADPH
octadecanal + NADP+
show the reaction diagram
octadecanoyl-CoA + NADPH + H+
octadecanal + CoA + NADP+
show the reaction diagram
octanoyl-CoA + NADPH + H+
octanal + CoA + NADP+
show the reaction diagram
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9% activity compared to hexadecanoyl-CoA
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-
?
oleoyl-CoA + NADPH + H+
oleic aldehyde + CoA + NADP+
show the reaction diagram
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78% activity compared to hexadecanoyl-CoA
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-
?
palmitoleoyl-CoA + NADPH + H+
palmitoleic aldehyde + CoA + NADP+
show the reaction diagram
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99% activity compared to hexadecanoyl-CoA
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-
?
tetradecanoyl-CoA + NAD(P)H
tetradecanal + NAD(P)+
show the reaction diagram
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-
-
?
tetradecanoyl-CoA + NADPH
tetradecanal + CoA + NADP+
show the reaction diagram
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-
-
?
tetradecanoyl-CoA + NADPH
tetradecanal + NADP+
show the reaction diagram
tetradecanoyl-CoA + NADPH + H+
tetradecanal + CoA + NADP+
show the reaction diagram
[hexadecanoyl]-acyl carrier protein + NADPH + H+
?
show the reaction diagram
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preferred 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
2-methyl-1-hexadecanoyl-CoA + NADPH + H+
2-methyl-1-hexadecanal + CoA + NADP+
show the reaction diagram
arachidonoyl-CoA + NADPH + H+
arachidonic aldehyde + CoA + NADP+
show the reaction diagram
-
86% activity compared to hexadecanoyl-CoA
-
-
?
cis-11-hexadecenal + CoA + NADP+
(E)-hexadec-11-enoyl-CoA + NADPh + H+
show the reaction diagram
-
-
-
-
?
dodecanoyl-CoA + NADPH + H+
dodecanal + CoA + NADP+
show the reaction diagram
-
26% activity compared to hexadecanoyl-CoA
-
-
?
heptadecanoyl-CoA + NADPH + H+
heptadecanal + CoA + NADP+
show the reaction diagram
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-
-
-
?
hexadecanoyl-CoA + NADPH + H+
1-hexadecanal + CoA + NADP+
show the reaction diagram
hexadecanoyl-CoA + NADPH + H+
hexadecanal + CoA + NADP+
show the reaction diagram
octadecanoyl-CoA + NADPH + H+
octadecanal + CoA + NADP+
show the reaction diagram
octanoyl-CoA + NADPH + H+
octanal + CoA + NADP+
show the reaction diagram
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9% activity compared to hexadecanoyl-CoA
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-
?
oleoyl-CoA + NADPH + H+
oleic aldehyde + CoA + NADP+
show the reaction diagram
-
78% activity compared to hexadecanoyl-CoA
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-
?
palmitoleoyl-CoA + NADPH + H+
palmitoleic aldehyde + CoA + NADP+
show the reaction diagram
-
99% activity compared to hexadecanoyl-CoA
-
-
?
tetradecanoyl-CoA + NADPH + H+
tetradecanal + CoA + NADP+
show the reaction diagram
[hexadecanoyl]-acyl carrier protein + NADPH + H+
?
show the reaction diagram
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preferred substrate
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-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
NADH
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NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
HgCl2
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p-chloromercuribenzoate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
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Lipids
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150% increase in activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
cis-11-hexadecenal
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at pH 7.0 and 37C
0.0036 - 0.029
hexadecanoyl-CoA
0.0016 - 0.0151
NADH
0.0032 - 0.067
NADPH
0.00146
[hexadecanoyl]-acyl carrier protein
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in 100 mM phosphate buffer, pH 7.0, at 30C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0024
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alcohol-generating enzyme
0.015
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using octanoyl-CoA as substrate, at pH 7.0 and 37C
0.034
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using dodecanoyl-CoA as substrate, at pH 7.0 and 37C
0.04
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using octadecanoyl-CoA as substrate, at pH 7.0 and 37C
0.044
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using oleoyl-CoA as substrate, at pH 7.0 and 37C
0.049
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using arachidonoyl-CoA as substrate, at pH 7.0 and 37C
0.057
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using hexadecanoyl-CoA as substrate, at pH 7.0 and 37C; using palmitoleyl-CoA as substrate, at pH 7.0 and 37C
0.96
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aldehyde-generating enzyme
321
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additional information
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20.0 light emission units/mg after 4 min incubation in luciferase coupled assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
49000
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gel filtration
85000 - 95000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 56000, SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
alcohol-generating and aldehyde-generating acyl-CoA reductases, Blue A agarose, gel filtration, hexadecanoyl-CoA affinity chromatography
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amylose column chromatography, metal affinity column chromatography, and G25 Sephadex gel filtration
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Blue A agarose, Sephacryl S-100, palmitoyl-CoA agarose
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heating, ammonium sulfate, gel filtration
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HisTrap column chromatography and Ni2+ resin column chromatography
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solubilization from microsomal preparation with 20% glycerol and 3 M NaCl, affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Rosetta (DE3) cells; expressed in Escherichia coli Rosetta (DE3) cells; expressed in Escherichia coli Rosetta (DE3) cells
expressed in Escherichia coli strain TB1
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expressed in Saccharomyces cerevisiae
expressed in Saccharomyces cerevisiae strain H1246
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expressed in Saccharomyces cerevisiae strain W303-1A and in Nicotiana benthamiana leaves
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expression in Escherichia coli
expression in Escherichia coli and Brassica napus
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C171S
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99% of wild-type activity
C279S
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79% of wild -type activity
C286S
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2% of wild-type activity
C171S
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77% of wild-type activity
C279S
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90% of wild-type activity
C286S
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9% of wild-type activity