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1.2.1.8: betaine-aldehyde dehydrogenase

This is an abbreviated version!
For detailed information about betaine-aldehyde dehydrogenase, go to the full flat file.

Word Map on EC 1.2.1.8

Reaction

Betaine aldehyde
+
NAD+
+
H2O
=
betaine
+
NADH
+ 2 H+

Synonyms

AcBADH, ALD10, aldehyde dehydrogenase, ALDH10, ALDH10A8, ALDH10A9, AMADH, AMADH1, aminoaldehyde dehydrogenase, BADH, BADH1, BADH2, badh2-E2, badh2-E7, betaine aldehyde dehydrogenase, betaine aldehyde dehydrogenase 1, betaine aldehyde dehydrogenase 1, chloroplastic, betaine aldehyde dehydrogenase 2, betaine aldehyde dehydrogenase, chloroplastic, betaine aldehyde oxidase, betaine aldehyde: NAD(P)+ oxidoreductase, betaine aldehyde: NAD+ oxidoreductase, betaine aldehyde:NAD(P)+ oxidoreductase, betaine aldehyde:NAD+ oxidoreductase, betaine-aldehyde dehydrogenase, BetB, dehydrogenase, betaine aldehyde, JcBD1, LcBADH, More, OsALDH10-1, OsALDH10-2, OsBADH1, OsBADH2, PaBADH, PaBADH2, pkBADH, PND BADH2, SACOL2628, YdcW, ZBD1, Zoysia betaine aldehyde dehydrogenase 1

ECTree

     1 Oxidoreductases
         1.2 Acting on the aldehyde or oxo group of donors
             1.2.1 With NAD+ or NADP+ as acceptor
                1.2.1.8 betaine-aldehyde dehydrogenase

Inhibitors

Inhibitors on EC 1.2.1.8 - betaine-aldehyde dehydrogenase

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INHIBITOR
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
-
10 mM, 18% inhibition
AgNO3
-
3 mM, 90-100% inhibition
benzaldehyde
-
1 mM, 51% inhibition
benzyltrimethylamine iodide
-
10 mM, 45% inhibition
betaine
Betaine aldehyde
bis[diethylthiocarbamyl]disulfide
-
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
cyclophosphamide
CTX, an antineoplastic and immuno-suppressant pre-drug, the enzyme loses 43% and 69% of its activity at 0.2 mM and 2.0 mM CTX, respectively, after 120 min. Docking of CTX to pkBADH and molecular modeling. The pseudofirst-order rate constant of inactivation (kobs) is dependent on CTX concentration only at low concentrations (0.2 and 0.6 mM CTX), and then the kobs between 1.0 and 2.0 mM show similar values. CTX can have access more easily to the catalytic cysteine when NAD+ opens the active site for substrate betaine aldehyde binding according to the kinetic mechanism, kinetics of inactivation of pkBADH by CTX in the presence of NADH, overview. Reversibility of inactivation, pkBADH inactivated with 2 mM CTX and incubated with DTT recovers 96% of its activity, and 93% with 2-mercaptoethanol, but in the presence of glutathione (GSH), the enzyme is not reactivated
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
-
10 mM, 93% inhibition
isopentanal
-
1 mM, 84% inhibition
Isovaleraldehyde
-
wild-type enzyme shows stronger inhibition than the mutant enzyme
methyl methanethiosulfonate
methyl methanethiosulphonate
-
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
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
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
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
-