Information on EC 1.2.1.42 - hexadecanal dehydrogenase (acylating)

for references in articles please use BRENDA:EC1.2.1.42
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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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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
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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
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Manually annotated by BRENDA team
barn owl
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
AtFAR2 is highly similar in properties and substrate specificity to AtFAR6
malfunction
mutations in specific genes encoding fatty acid reductases (FAR) re­sponsible for fatty alcohol production cause abnormal development of pollen. A disrupted AtFAR2 (MS2) gene in Arabidopsis thaliana results in pollen developing an abnormal exine layer and a reduced fertility pheno­type
physiological function
AtFAR2 is a fatty acid reductase from Arabidopsis thaliana that reduces fatty acyl-CoA and -ACP substrates into fatty alcohols, cf. EC 1.2.1.80. Enzyme AtFAR2 is the major enzyme respon­sible for exine layer functionality, AtFAR6 might provide functional redundancy to AtFAR2
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
acetyl-CoA + NADH + H+
acetaldehyde + CoA + NAD+
show the reaction diagram
-
-
-
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r
arachidonoyl-CoA + NADPH + H+
arachidonic aldehyde + CoA + NADP+
show the reaction diagram
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86% activity compared to hexadecanoyl-CoA
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-
?
butanoyl-CoA + NADH + H+
butanal + CoA + NAD+
show the reaction diagram
-
-
-
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r
cis-11-hexadecenal + CoA + NADP+
(E)-hexadec-11-enoyl-CoA + NADPh + H+
show the reaction diagram
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-
-
-
?
decanoyl-CoA + NAD(P)H
decanal + NAD(P)+
show the reaction diagram
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2.5% of activity with tetradecanoyl-CoA
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?
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
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?
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
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?
eicosanoyl-CoA + NADPH
eicosanal + NADP+
show the reaction diagram
heptadecanoyl-CoA + NADPH + H+
heptadecanal + CoA + NADP+
show the reaction diagram
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-
-
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?
hexadecanal + CoA + NAD+
hexadecanoyl-CoA + NADH + H+
show the reaction diagram
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-
-
?
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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-
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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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-
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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
acetyl-CoA + NADH + H+
acetaldehyde + CoA + NAD+
show the reaction diagram
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-
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r
arachidonoyl-CoA + NADPH + H+
arachidonic aldehyde + CoA + NADP+
show the reaction diagram
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86% activity compared to hexadecanoyl-CoA
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?
butanoyl-CoA + NADH + H+
butanal + CoA + NAD+
show the reaction diagram
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-
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r
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
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?
heptadecanoyl-CoA + NADPH + H+
heptadecanal + CoA + NADP+
show the reaction diagram
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-
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?
hexadecanal + CoA + NAD+
hexadecanoyl-CoA + NADH + H+
show the reaction diagram
Q08891
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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
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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 + 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
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
0.076
acetyl-CoA
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recombinant enzyme, pH 7.15, 30°C
0.256
Butanoyl-CoA
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recombinant enzyme, pH 7.15, 30°C
0.05
cis-11-hexadecenal
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at pH 7.0 and 37°C
0.00531
hexadecanal
pH 7.0, 30°C, recombinant enzyme
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 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08
acetyl-CoA
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recombinant enzyme, pH 7.15, 30°C
0.19
Butanoyl-CoA
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recombinant enzyme, pH 7.15, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.1
acetyl-CoA
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recombinant enzyme, pH 7.15, 30°C
0.7
Butanoyl-CoA
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recombinant enzyme, pH 7.15, 30°C
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 37°C
0.034
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using dodecanoyl-CoA as substrate, at pH 7.0 and 37°C
0.04
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using octadecanoyl-CoA as substrate, at pH 7.0 and 37°C
0.044
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using oleoyl-CoA as substrate, at pH 7.0 and 37°C
0.049
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using arachidonoyl-CoA as substrate, at pH 7.0 and 37°C
0.057
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using hexadecanoyl-CoA as substrate, at pH 7.0 and 37°C; using palmitoleyl-CoA as substrate, at pH 7.0 and 37°C
0.96
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aldehyde-generating enzyme
2.2
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about, with butanoyl-CoA, pH 7.15, 30°C
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
6
with aldehyde substrates
7.2
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additional information
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
28000
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x * 28000, aldehyde-generating enzyme, SDS-PAGE
32000
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x * 32000, enzyme expressed in Escherichia coli, SDS-PAGE
33000
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x * 33000, enzyme expressed in Escherichia coli, SDS-PAGE
49000
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gel filtration
58000
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x * 58000, alcohol-generating enzyme, SDS-PAGE
85000 - 95000
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gel filtration
116000
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x * 116000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 56000, SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
the enzyme is oxygen-tolerant
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742372
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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recombinant His-tagged enzyme from Escherichia coli strain Rosetta (DE3) by nickel affinity chromatography
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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gene FAR2, recombinant expression of His-tagged enzyme in Escherichia coli strain Rosetta (DE3), transient expression of GFP-tagged FAR2 in Nicotiana benthamiana leaves under control of CaMV 35S promoter via Agrobacterium tumefaciens strain V3101::pMP90 transfection method
gene pduP, recombinant expression in Escherichia coli strain JCL166, strain JCL166 cannot grow anaerobically unless complemented by an exogenous fermentation pathway such as n-butanol biosynthesis. Recombinant coexpression of PduP with the enzymes of the n-butanol synthesis pathway in Synechococcus elongatus strain PCC 7942 does not result in autotrophic n-butanol production, the enzyme from Porphyromonas gingivalis cannot enable anaerobic growth rescue
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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