Information on EC 1.2.1.8 - betaine-aldehyde dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.2.1.8
-
RECOMMENDED NAME
GeneOntology No.
betaine-aldehyde dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
betaine aldehyde + NAD+ + H2O = betaine + NADH + 2 H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
choline degradation I
-
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glycine betaine biosynthesis II (Gram-positive bacteria)
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glycine betaine biosynthesis I (Gram-negative bacteria)
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glycine betaine biosynthesis III (plants)
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choline degradation IV
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glycine betaine biosynthesis
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Glycine, serine and threonine metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
betaine-aldehyde:NAD+ oxidoreductase
In many bacteria, plants and animals, the osmoprotectant betaine is synthesized in two steps: (1) choline to betaine aldehyde and (2) betaine aldehyde to betaine. This enzyme is involved in the second step and appears to be the same in plants, animals and bacteria. In contrast, different enzymes are involved in the first reaction. In plants, this reaction is catalysed by EC 1.14.15.7 (choline monooxygenase), whereas in animals and many bacteria it is catalysed by either membrane-bound EC 1.1.99.1 (choline dehydrogenase) or soluble EC 1.1.3.17 (choline oxidase) [5]. In some bacteria, betaine is synthesized from glycine through the actions of EC 2.1.1.156 (glycine/sarcosine N-methyltransferase) and EC 2.1.1.157 (sarcosine/dimethylglycine N-methyltransferase).
CAS REGISTRY NUMBER
COMMENTARY hide
9028-90-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
Amaranthus sp.
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Manually annotated by BRENDA team
P1
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Manually annotated by BRENDA team
P1
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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
544
UniProt
Manually annotated by BRENDA team
544
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
variety 634920 Zhe
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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
cultivar Xushu 18
UniProt
Manually annotated by BRENDA team
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UniProt
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
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
-
betaine aldehyde dehydrogenase 2 is a key enzyme in the synthesis of fragrance aroma compounds. The extremely low activity of the enzyme in catalyzing the oxidation of acetaldehyde is crucial for the accumulation of the volatile compound 2-acetyl-1-pyrroline in fragrant rice
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
1,3-diaminopropane + NAD+ + H2O
?
show the reaction diagram
-
-
-
-
?
3-aminopropionaldehyde + NAD(P)+ + H2O
?
show the reaction diagram
-
-
-
-
?
3-aminopropionaldehyde + NAD+ + H2O
3-aminopropanoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-aminopropionaldehyde + NAD+ + H2O
3-aminopropionate + NADH + H+
show the reaction diagram
3-aminopropionaldehyde + NAD+ + H2O
3-aminopropionic acid + NADH + H+
show the reaction diagram
3-aminopropionaldehyde + NAD+ + H2O
?
show the reaction diagram
3-dimethylsulfoniopropionaldehyde + NAD(P)+ + H2O
?
show the reaction diagram
-
-
-
-
?
3-dimethylsulfoniopropionaldehyde + NAD+ + H2O
?
show the reaction diagram
-
-
-
-
?
3-dimethylsulfoniopropionaldehyde + NAD+ + O2
3-dimethylsulfoniopropionate + NADH
show the reaction diagram
-
steady state bi bi mechanism with ordered addition of substrates and random release of products
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-
ir
3-N-trimethylaminopropionaldehyde + NAD+ + H2O
3-N-trimethylaminopropanoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-N-trimethylaminopropionaldehyde + NAD+ + H2O
3-N-trimethylaminopropionate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-N-trimethylaminopropionaldehyde + NAD+ + H2O
?
show the reaction diagram
4-aminobutanal + NAD+ + H2O
4-aminobutanoate + NADH
show the reaction diagram
-
-
-
-
?
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutanoate + NADH + H+
show the reaction diagram
-
-
-
-
?
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutyrate + NADH
show the reaction diagram
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutyrate + NADH + H+
show the reaction diagram
-
-
-
?
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutyric acid + NADH + H+
show the reaction diagram
4-gamma-aminobutyraldehyde + NAD+ + H2O
?
show the reaction diagram
4-guanidinobutyraldehyde + NAD+ + H2O
4-guanidinobutyrate + NADH + H+
show the reaction diagram
-
-
-
-
?
4-guanidinobutyraldehyde + NAD+ + H2O
?
show the reaction diagram
4-N-trimethylaminobutyraldehyde + NAD(P)+ + H2O
?
show the reaction diagram
-
-
-
-
?
4-N-trimethylaminobutyraldehyde + NAD+ + H2O
4-N-trimethylaminobutyrate + NADH + H+
show the reaction diagram
-
-
-
-
?
4-N-trimethylaminobutyraldehyde + NAD+ + H2O
4-N-trmethylaminobutanoate + NADH + H+
show the reaction diagram
-
-
-
-
?
4-N-trimethylaminobutyraldehyde + NAD+ + H2O
?
show the reaction diagram
4-trimethylaminobutyraldehyde + NAD+ + H2O
3-trimethylaminobutyrate + NADH
show the reaction diagram
-
-
-
-
?
acetaldehyde + NAD+ + H2O
acetate + NADH + H+
show the reaction diagram
acetaldehyde + NADP+ + H2O
acetate + NADPH + H+
show the reaction diagram
-
-
-
-
?
aminoacetaldehyde + NAD+ + H2O
aminoacetate + NADH + H+
show the reaction diagram
-
-
-
-
?
benzaldehyde + NAD+ + H2O
benzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
benzaldehyde + NADP+ + H2O
benzoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
betaine aldehyde + NAD(P)+ + H2O
betaine + NAD(P)H + H+
show the reaction diagram
-
-
-
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?
betaine aldehyde + NAD(P)+ + H2O
glycine betaine + NAD(P)H + 2 H+
show the reaction diagram
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-
-
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ir
betaine aldehyde + NAD(P)+ + H2O
glycine betaine + NAD(P)H + H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH + 2 H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH + H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
glycine betaine + NADH + 2 H+
show the reaction diagram
-
-
-
r
betaine aldehyde + NAD+ + H2O
glycine betaine + NADH + H+
show the reaction diagram
betaine aldehyde + NADP+ + H2O
betaine + NADPH
show the reaction diagram
betaine aldehyde + NADP+ + H2O
betaine + NADPH + H+
show the reaction diagram
betaine aldehyde + NADP+ + H2O
glycine betaine + NADPH + H+
show the reaction diagram
-
-
-
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ir
butyraldehyde + NAD+ + H2O
butyrate + NADH
show the reaction diagram
-
at 40% of the activity with betaine aldehyde
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-
?
butyraldehyde + NAD+ + H2O
butyrate + NADH + H+
show the reaction diagram
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-
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?
butyraldehyde + NADP+ + H2O
butyrate + NADPH + H+
show the reaction diagram
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-
-
-
?
DL-glyceraldehyde + NAD+ + H2O
glycerate + NADH + H+
show the reaction diagram
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-
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?
DL-glyceraldehyde + NADP+ + H2O
glycerate + NADPH + H+
show the reaction diagram
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-
-
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?
formaldehyde + NAD+ + H2O
formate + NADH + H+
show the reaction diagram
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-
-
-
?
formaldehyde + NADP+ + H2O
formate + NADPH + H+
show the reaction diagram
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-
-
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?
gamma-aminobutyraldehyde + NAD(P)+ + H2O
?
show the reaction diagram
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-
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?
glyceraldehyde + NAD+ + H2O
glycerate + NADH
show the reaction diagram
-
at 30% of the activity with betaine aldehyde
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?
glycine betaine aldehyde + NAD+ + H2O
glycine betaine + NADH
show the reaction diagram
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-
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?
glycine betaine aldehyde + NADP+ + H2O
glycine betaine + NADPH
show the reaction diagram
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-
-
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?
glycolaldehyde + NAD+ + H2O
glycolate + NADH
show the reaction diagram
glycolaldehyde + NAD+ + H2O
glycolate + NADH + H+
show the reaction diagram
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-
-
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?
glycolaldehyde + NADP+ + H2O
glycolate + NADPH + H+
show the reaction diagram
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-
-
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?
isovaleraldehyde + NAD+ + H2O
isovalerate + NADH + H+
show the reaction diagram
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-
-
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?
isovaleraldehyde + NADP+ + H2O
isovalerate + NADPH + H+
show the reaction diagram
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-
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?
methylglyoxal + NAD+ + H2O
pyruvate + NADH + H+
show the reaction diagram
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-
-
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?
methylglyoxal + NADP+ + H2O
? + NADPH + H+
show the reaction diagram
-
-
-
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?
N-acetyl-4-aminobutyraldehyde + NAD+ + H2O
?
show the reaction diagram
-
-
-
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?
p-nitrobenzaldehyde + NAD+ + H2O
p-nitrobenzoate + NADH + H+
show the reaction diagram
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-
-
-
?
p-nitrobenzaldehyde + NADP+ + H2O
p-nitrobenzoate + NADPH + H+
show the reaction diagram
-
-
-
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?
phenyl acetaldehyde + NAD+ + H2O
phenyl acetate + NADH + H+
show the reaction diagram
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-
-
-
?
phenyl acetaldehyde + NADP+ + H2O
phenyl acetate + NADPH + H+
show the reaction diagram
-
-
-
-
?
propionaldehyde + NAD+ + H2O
propionate + NADH
show the reaction diagram
-
-
-
-
?
propionaldehyde + NAD+ + H2O
propionate + NADH + H+
show the reaction diagram
-
-
-
-
?
propionaldehyde + NADP+ + H2O
propionate + NADPH + H+
show the reaction diagram
-
-
-
-
?
undecanal + NAD+ + H2O
undecanoate + NADH + H+
show the reaction diagram
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-
-
-
?
undecanal + NADP+ + H2O
undecanoate + NADPH + H+
show the reaction diagram
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-
-
-
?
valeraldehyde + NAD+ + H2O
valerate + NADH + H+
show the reaction diagram
-
-
-
-
?
valeraldehyde + NADP+ + H2O
valerate + NADPH + H+
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
3-aminopropionaldehyde + NAD+ + H2O
3-aminopropionate + NADH + H+
show the reaction diagram
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutyrate + NADH + H+
show the reaction diagram
B3VMC0, B3VMC1, B3VMC2
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-
-
?
4-aminobutyraldehyde + NAD+ + H2O
4-aminobutyric acid + NADH + H+
show the reaction diagram
betaine aldehyde + NAD(P)+ + H2O
glycine betaine + NAD(P)H + 2 H+
show the reaction diagram
-
-
-
-
ir
betaine aldehyde + NAD(P)+ + H2O
glycine betaine + NAD(P)H + H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH + 2 H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
betaine + NADH + H+
show the reaction diagram
betaine aldehyde + NAD+ + H2O
glycine betaine + NADH + 2 H+
show the reaction diagram
Q9HTJ1
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-
-
r
betaine aldehyde + NAD+ + H2O
glycine betaine + NADH + H+
show the reaction diagram
betaine aldehyde + NADP+ + H2O
betaine + NADPH + H+
show the reaction diagram
betaine aldehyde + NADP+ + H2O
glycine betaine + NADPH + H+
show the reaction diagram
-
-
-
-
ir
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
0.2 M, slight activation
additional information
-
high salt tolerance: 50% or more of its maximal activity is preserved at 1.0 M Na+ or K+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(NH4)2SO4
-
mutant enzyme is less sensitive to inhibition than wild-type enzyme
1,10-phenanthroline
2,2'-dipyridyl
3-dimethylsulfoniopropionaldehyde
-
at high concentrations
5,5'-dithiobis[2-nitrobenzoic acid]
-
the effect of the thiol reagent DTNB on the native enzyme structure of the wild type enzyme and the mutants is examined
acetaldehyde
Acetylcholine
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10 mM, 18% inhibition
AgNO3
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3 mM, 90-100% inhibition
benzaldehyde
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1 mM, 51% inhibition
benzyltrimethylamine iodide
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10 mM, 45% inhibition
betaine
Betaine aldehyde
bis[diethylthiocarbamyl]disulfide
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the effect of the thiol reagent disulfiram on the native enzyme structure of the wild type enzyme and the mutants is examined
Butyrylcholine
-
100 mM, 73% inhibition
choline
cimetidine
Disulfiram
DL-glyceraldehyde
-
-
ethanolamine
-
100 mM, 35% inhibition
Glutaraldehyde
-
10 mM, 83% inhibition
glyceraldehyde
-
100 mM, 83% inhibition
glycine betaine
H2O2
-
more than 50% inhibition at 0.1 mM H2O2, noncompetitive inhibition with respect to NAD+ or to betaine aldehyde at saturating concentrations of the other substrate at pH 7.0 or 8.0
iodoacetamide
iodoacetate
Iodosobenzoate
-
-
Isobutanal
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10 mM, 93% inhibition
isopentanal
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1 mM, 84% inhibition
Isovaleraldehyde
-
wild-type enzyme shows stronger inhibition than the mutant enzyme
K+
-
1.0 mM, 35% inhibition
methyl methanethiosulfonate
methyl methanethiosulphonate
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pH-dependence of the second-order rate constant of inactivation suggests that at low pH values the essential Cys exists as thiolate by the formation of an ion pair with a positively charged residue
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methyl(bis-beta-chloroethyl)amine
-
-
Mg2+
-
0.4 M, complete inhibition
N,N-dimethylethanolamine
-
100 mM, 57% inhibition
N,N-dimethylglycine
-
1 mM, 24% inhibition
n-butylaldehyde
-
10 mM, 96% inhibition
N-ethylmaleimide
-
-
N-Methylethanolamine
-
100 mM, 50% inhibition
N-methylglycine
-
1 mM, 24% inhibition
NAD(P)H
-
reversible inactivation
NADP+
-
substrate inhibition above 10 mM
NADPH
-
product inhibition
phenylacetaldehyde
-
1 mM, 54% inhibition
Phenylarsine oxide
-
PAO
phosphate
-
-
S-methyl-N,N-diethyldithiocarbamoyl sulfone
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most potent irreversible inhibition in vitro at 0.05 mM, but no inhibition in situ
S-methyl-N,N-diethyldithiocarbamoyl sulfoxide
-
irreversible inhibition
S-methyl-N,N-diethylthiocarbamoyl sulfone
-
irreversible inhibition
S-methyl-N,N-diethylthiocarbamoyl sulfoxide
-
-
S-methylmethanesulfonate
-
the effect of the thiol reagent MMTS on the native enzyme structure of the wild type enzyme and the mutants is examined
sodium meta-arsenite plus 2,3-dimercaptopropanol
-
arsenite-BAL
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tetraethylamine iodide
-
10 mM, 19% inhibition
tetramethylamine iodide
-
10 mM, 19% inhibition
tetramethylammonium hydroxide
-
100 mM, 57% inhibition
tetrapropylamine iodide
-
10 mM, 43% inhibition
trimethylacetaldehyde
-
100 mM, 89% inhibition
ZnCl2
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cys
-
activates, optimal concentration: 1 mM
dithiothreitol
-
enhances activity
glycine betaine
-
activates the wild-type enzyme but not the mutant enzyme
KCl
maximum activity at 0.5 M
methanol
used in the assay as activating compound in concentration of 0.5% for 96 h
NH4+
-
slight activation up to about 0.3 M
Pro
-
0.1 M, 35% activation, at high substrate concentrations
propan-2-yl 1-thio-beta-D-galactopyranoside
-
for the expressed protein, final concentration of 1 mmol in culture solution
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000054 - 3.7
3-aminopropionaldehyde
0.0027
3-dimethylsulfoniopropionaldehyde
-
-
0.035 - 0.34
3-N-trimethylaminopropionaldehyde
0.00196 - 1.1
4-Aminobutyraldehyde
0.000024 - 0.00005
4-Guanidinobutyraldehyde
0.0078 - 0.041
4-N-trimethylaminobutyraldehyde
0.0014
4-trimethylaminobutyraldehyde
-
cytoplasmic enzyme
0.014 - 28
acetaldehyde
0.1 - 6.7
benzaldehyde
0.0000041
beta-NAD+
-
-
0.000005 - 14.8
Betaine aldehyde
0.5 - 3.4
Butyraldehyde
11 - 48
D,L-glyceraldehyde
3.8
formaldehyde
-
pH 7.7, coenzyme NAD+
0.13
glycine betaine aldehyde
-
-
0.152 - 11.5
glycolaldehyde
0.2 - 15
Isovaleraldehyde
2.5 - 9
methylglyoxal
0.0025 - 3.42
NAD+
0.08 - 3.68
NADP+
0.5
p-nitrobenzaldehyde
-
pH 7.7, coenzyme NAD+
51 - 140
phenyl acetaldehyde
0.8 - 21
propionaldehyde
2 - 106
Undecanal
0.2 - 4.1
Valeraldehyde
additional information
additional information
-
for the mutants and wild-type enzymes KM NADP+ varies within 0.060 and 0.107 mM, KM NAD+ within 0.254 and 0.411 mM, KM betaine aldehyde within 0.270 and 0.434 mM
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1 - 11
Betaine aldehyde
0.39 - 261
NAD+
0.56 - 276
NADP+
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.053 - 64.7
Betaine aldehyde
22 - 243
NAD+