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(3-carboxypropyl)(trimethyl)arsanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + succinate + CO2
(3-carboxypropyl)(trimethyl)phosphanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + succinate + CO2
(3R)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + formylfluoride
(3R)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
?
-
weak substrate, below 5% turnover after 3 h
-
-
?
(3S)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
?
-
S-stereoisomer preferred substrate
-
-
?
(R)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3R)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
(S)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3S)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
(S)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
(3S)-3-carboxy-2,3-dihydroxy-N,N,N-trimethylpropan-1-aminium + succinate + CO2
-
-
-
?
2-carboxy-N,N,N-trimethylethan-1-aminium + 2-oxoglutarate + O2
4-carboxy-3-hydroxy-N,N,N-trimethylbutan-1-aminium + succinate + CO2
3-carboxy-N-(fluoromethyl)-N,N-dimethylpropan-1-aminium + 2-oxoglutarate + O2
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium + succinate + CO2
3-trimethylaminopropionic acid + 2-oxoglutarate + O2
?
-
20% of the hydroxylation rate of gamma-butyrobetaine
-
-
?
4-(trimethylammonio)butanoic acid + 2-oxoglutarate + O2
?
-
-
-
-
?
4-dimethylaminobutyric acid + 2-oxoglutarate + O2
4-dimethylamino-3-hydroxybutyric acid + succinate + CO2
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
4-trimethylammoniopropanoate + 2-oxoglutarate + O2
2-carboxy-2-hydroxy-N,N,N-trimethylethan-1-aminium + succinate + CO2
-
-
-
?
5,5-dimethylhexanoate + 2-oxoglutarate + O2
?
6-N-trimethyl-L-lysine + 2-oxoglutarate + O2
?
-
-
-
-
?
D-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
gamma-butyrobetaine + 2-oxoglutarate + O2
carnitine + succinate + CO2
L-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
mildronate + O2
?
both a relatively weak BBOX inhibitor in vitro and a competitive substrate producing multiple products
-
-
?
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)phosphanium + succinate + CO2
-
-
-
?
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2
-
-
-
?
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)phosphanium + succinate + CO2
-
-
-
?
additional information
?
-
(3-carboxypropyl)(trimethyl)arsanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + succinate + CO2
-
-
-
?
(3-carboxypropyl)(trimethyl)arsanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + succinate + CO2
-
-
-
?
(3-carboxypropyl)(trimethyl)phosphanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + succinate + CO2
-
-
-
?
(3-carboxypropyl)(trimethyl)phosphanium + 2-oxoglutarate + O2
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + succinate + CO2
-
-
-
?
(3R)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + formylfluoride
-
-
-
?
(3R)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + formylfluoride
-
-
-
?
(3R)-3-fluoro-4-(trimethylammonio)butanoate + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + formylfluoride
-
-
-
?
(R)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3R)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
-
-
-
?
(R)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3R)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
-
-
-
?
(S)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3S)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
-
-
-
?
(S)-2-amino-3-carboxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2
N-[(3S)-3-amino-3-carboxy-2-hydroxypropyl]-N,N-dimethylmethanaminium + succinate + CO2
-
-
-
?
2-carboxy-N,N,N-trimethylethan-1-aminium + 2-oxoglutarate + O2
4-carboxy-3-hydroxy-N,N,N-trimethylbutan-1-aminium + succinate + CO2
-
-
-
?
2-carboxy-N,N,N-trimethylethan-1-aminium + 2-oxoglutarate + O2
4-carboxy-3-hydroxy-N,N,N-trimethylbutan-1-aminium + succinate + CO2
-
-
-
?
3-carboxy-N-(fluoromethyl)-N,N-dimethylpropan-1-aminium + 2-oxoglutarate + O2
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium + succinate + CO2
-
-
-
?
3-carboxy-N-(fluoromethyl)-N,N-dimethylpropan-1-aminium + 2-oxoglutarate + O2
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium + succinate + CO2
-
-
-
?
4-dimethylaminobutyric acid + 2-oxoglutarate + O2
4-dimethylamino-3-hydroxybutyric acid + succinate + CO2
-
-
-
-
?
4-dimethylaminobutyric acid + 2-oxoglutarate + O2
4-dimethylamino-3-hydroxybutyric acid + succinate + CO2
-
-
-
-
?
4-dimethylaminobutyric acid + 2-oxoglutarate + O2
4-dimethylamino-3-hydroxybutyric acid + succinate + CO2
-
poor substrate
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
gamma-butyrobetaine, terminal reaction in the pathway of L-carnitine biosynthesis
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
catalytic domain and active site structure, overview
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
-
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
i.e. gamma-butyrobetaine
i.e. L-carnitine
?
4-trimethylammoniobutanoate + 2-oxoglutarate + O2
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2
-
-
-
?
5,5-dimethylhexanoate + 2-oxoglutarate + O2
?
-
poor substrate, 20% of the decarboxylation events lead to hydroxylation
-
-
?
5,5-dimethylhexanoate + 2-oxoglutarate + O2
?
-
poor substrate, 20% of the decarboxylation events lead to hydroxylation
-
-
?
D-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
-
-
-
?
D-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
-
-
-
?
D-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
-
-
-
-
r
gamma-butyrobetaine + 2-oxoglutarate + O2
carnitine + succinate + CO2
-
-
-
-
?
gamma-butyrobetaine + 2-oxoglutarate + O2
carnitine + succinate + CO2
-
-
-
-
?
L-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
-
-
-
?
L-carnitine + 2-oxoglutarate + O2
3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2
-
-
-
-
r
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2
-
-
-
?
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2
(3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2
-
-
-
?
additional information
?
-
-
L-carnithine is an uncoupler
-
-
?
additional information
?
-
no activity with trimethyllysine, acetylcholine, phosphocholine, thioacetylcholine, carbachol, and gamma-butyrobetaine analogues carboxy-N,N,N-trimethylmethanaminium, 5-carboxy-N,N,N-trimethylpentan-1-aminium, N,N,N-trimethyl-4-oxopentan-1-aminium, and 4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium, substrate specificity, overview
-
-
?
additional information
?
-
-
both enhancement of carnitine biosynthesis due to increased gamma-butyrobetaine dioxygenase activity, extra-hepatic gamma-butyrobetaine synthesis and increased hepatic carnitine import contributes to the increased hepatic carnitine levels after fasting
-
-
?
additional information
?
-
-
overview on properties of substrate analogues, binding sites
-
-
?
additional information
?
-
-
L-carnithine is an uncoupler
-
-
?
additional information
?
-
cation-Pi interactions contribute to substrate recognition in gamma-butyrobetaine hydroxylase catalysis. BBOX contains an aromatic cage for the recognition of the positively charged trimethylammonium group of the gamma-butyrobetaine substrate. Substrate analogues (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium with P and As substituting for N in the trimethylammonium group are good BBOX substrates, which follow the efficiency trend N+ >P+ >As+. An uncharged carbon analogue N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine of gamma-butyrobetaine is not a BBOX substrate. Importance of the energetically favorable cation-Pi interactions in productive substrate recognition. Homology modeling of binding modes and structures of (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium to psBBOX using an X-ray crystal structure of human BBOX in complex with ZnII, N-oxalylglycine, and gamma-butyrobetaine, PDB ID 3O2G, quantum mechanical calculations and docking simulations. Substrate specificity, overview
-
-
?
additional information
?
-
no activity with trimethyllysine, acetylcholine, phosphocholine, thioacetylcholine, carbachol, and gamma-butyrobetaine analogues carboxy-N,N,N-trimethylmethanaminium, 5-carboxy-N,N,N-trimethylpentan-1-aminium, N,N,N-trimethyl-4-oxopentan-1-aminium, and 4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium, substrate specificity, overview
-
-
?
additional information
?
-
cation-Pi interactions contribute to substrate recognition in gamma-butyrobetaine hydroxylase catalysis. BBOX contains an aromatic cage for the recognition of the positively charged trimethylammonium group of the gamma-butyrobetaine substrate. Substrate analogues (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium with P and As substituting for N in the trimethylammonium group are good BBOX substrates, which follow the efficiency trend N+ >P+ >As+. An uncharged carbon analogue N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine of gamma-butyrobetaine is not a BBOX substrate. Importance of the energetically favorable cation-Pi interactions in productive substrate recognition. Homology modeling of binding modes and structures of (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium to psBBOX using an X-ray crystal structure of human BBOX in complex with ZnII, N-oxalylglycine, and gamma-butyrobetaine, PDB ID 3O2G, quantum mechanical calculations and docking simulations. Substrate specificity, overview
-
-
?
additional information
?
-
no activity with trimethyllysine, acetylcholine, phosphocholine, thioacetylcholine, carbachol, and gamma-butyrobetaine analogues carboxy-N,N,N-trimethylmethanaminium, 5-carboxy-N,N,N-trimethylpentan-1-aminium, N,N,N-trimethyl-4-oxopentan-1-aminium, and 4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium, substrate specificity, overview
-
-
?
additional information
?
-
-
L-carnithine is an uncoupler
-
-
?
additional information
?
-
-
overview on properties of substrate analogues, binding sites
-
-
?
additional information
?
-
enzyme is involved in L-carnitine (3-hydroxy-4-N-trimethylaminobutyrate) biosynthesis
-
-
?
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(3-carboxy-2-oxopropyl)(trimethyl)arsanium
-
(3-carboxy-2-oxopropyl)(trimethyl)phosphanium
-
(3-carboxypropyl)(trimethyl)arsanium
-
(3-carboxypropyl)(trimethyl)phosphanium
-
(3R)-3-fluoro-4-(trimethylammonio)butanoate
-
(E)-4-(trimethylammonio)but-2-enoate
-
1,1,1-trimethyl-2-(2-phosphonoethyl)hydrazin-1-ium Iodide
-
1-(3-carboxypropyl)-1-methylpyrrolidin-1-ium
-
1-(3-carboxypropyl)pyrrolidin-1-ium
-
2-(1,1,1-trimethylhydrazin-1-ium-2-yl)ethanesulfonate
-
2-(2-carboxyethyl)-1,1-diethyl-1-methylhydrazin-1-ium chloride
-
2-(2-carboxyethyl)-1,1-dimethyl-1-(prop-2-yn-1-yl)-hydrazin-1-ium bromide
-
2-(2-carboxyethyl)-1-(2-chloroethyl)-1,1-dimethylhydrazin-1-ium bromide
-
2-oxoglutarate
-
at concentrations above 1 mM
3,4-dihydroxybenzoate
-
-
3-(1,1,1,2-tetramethylhydrazin-1-ium-2-yl)propanoate
-
3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate
3-(1,1,2-trimethyl-1-propylhydrazin-1-ium-2-yl)propanoate
-
3-(1,1-dimethyl-1-vinylhydrazin-1-ium-2-yl)propanoate
-
-
3-(1-allyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
-
3-(1-ethyl-1,1,2-trimethylhydrazin-1-ium-2-yl)propanoate
-
3-(1-ethyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
-
3-(1-isopropyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
-
3-(2,2,2-trimethylhydrazinium propionate dihydrate)
i.e. mildronate, a synthetic inhibitor of GBBH, is a non-hydroxylatable analog of gamma-butyrobetaine
3-(2,2,2-trimethylhydrazinium)propionate
-
complete inhibition at 0.05 mM
3-(2,2,2-trimethylhydrazinium)propionate dihydrate
-
-
3-(2,2-Dimethylcyclopropyl)propionic acid
-
mechanism-based inhibitor
3-(2-ethyl-1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate
-
3-(ethyldimethylammonio)propane-1-sulfonate
-
3-(trimethylammonio)cyclohexanecarboxylate
-
3-(trimethylammonio)propane-1-sulfonate
-
3-Bromo-2-oxoglutarate
-
noncompetitive inhibition, 2-oxoglutarate as variable substrate
3-carboxy-2-chloro-N,N,N-trimethylpropan-1-aminium
-
3-carboxy-N-(2-chloroethyl)-N,N-dimethylpropan-1-aminium
-
3-carboxy-N-(2-fluoroethyl)-N,N-dimethylpropan-1-aminium
-
3-carboxy-N-(fluoromethyl)-N,N-dimethylpropan-1-aminium
-
3-glutathione-2-oxoglutarate
-
noncompetitive to 2-oxoglutarate
3-hydroxy-N-(2-phenylethyl)pyridine-2-carboxamide
weak inhibition
3-trimethylaminopropyl-1-sulfonate
-
-
3-[1-(2-aminoethyl)-1,1-dimethylhydrazin-1-ium-2-yl]-propanoate
-
3-[1-(2-hydroxyethyl)-1,1-dimethylhydrazin-1-ium-2-yl]-propanoate
-
-
4-(allyldimethylammonio)butanoate
-
4-(benzyldimethylammonio)butanoate
-
4-(butyldimethylammonio)butanoate
-
4-(cyclobutyldimethylammonio)butanoate
-
4-(cyclopentyldimethylammonio)butanoate
-
4-(cyclopropyldimethylammonio)butanoate
-
4-(dimethylsulfonio)butanoate
-
4-(ethyldimethylammonio)butanoate
-
4-(trimethylammonio)pentanoate
-
4-([(2E)-3-carboxyprop-2-enoyl](hydroxy)amino)-N,N,N-trimethylbutan-1-aminium
i.e. RL190B
-
4-Trimethylammoniobutanoate
4-[(2-hydroxyethyl)dimethylammonio]butanoate
-
4-[(bromomethyl)dimethylammonio]butanoate
-
4-[(chloromethyl)dimethylammonio]butanoate
-
4-[(cyclobutylmethyl)dimethylammonio]butanoate
-
4-[(cyclopropylmethyl)dimethylammonio]butanoate
-
4-[(iodomethyl)dimethylammonio]butanoate
-
4-[(methoxymethyl)dimethylammonio]butanoate
-
4-[diethyl(methyl)ammonio]butanoate
-
4-[dimethyl(prop-2-yn-1-yl)ammonio]butanoate
-
4-[dimethyl(propyl)ammonio]butanoate
-
4-[dimethyl(vinyl)ammonio]butanoate
-
4-[isopropyl(dimethyl)ammonio]butanoate
-
5-(trimethylammonio)pentanoate
-
alpha,alpha'-bipyridyl
-
no activity at 2 mM
AR692B
a potent and selective inhibitor for human enzyme BBOX, binds in two modes, one of which adopts an unusual U-shape conformation stabilised by inter- and intra-molecular Pi-stacking interactions. Conformational changes observed on binding of the inhibitor to BBOX likely reflect those occurring in catalysis. The BBOX-AR692B with and without substrate/ inhibitor crystal structures (PDB ID 3O2G/3N6W) reveal substantial conformational differences
benzeneselenenyl bromide
-
benzeneselenenyl chloride
-
Clofibrate
-
activity of gamma-butyrobetaine dioxygenase in the liver is lower in pigs treated with clofibrate than in control pigs
cyclopropyl-substituted gamma-butyrobetaines
-
-
-
D-carnitine
-
uncoupling agent
ebselen
a relatively potent BBOX inhibitor and a Zn(II) ejector
FMN
-
in high concentrations
iodoacetate
-
less effective than p-chloromercuriphenylsulfonate
Iodosobenzoate
-
less effective than p-chloromercuriphenylsulfonate
N,N,N-trimethyl-3-(1H-tetrazol-5-yl)propan-1-aminium
-
N,N,N-trimethyl-3-phosphonopropan-1-aminium
-
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)-L-tryptophan
-
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
N-(2-bromoethyl)-3-carboxy-N,N-dimethylpropan-1-aminium
-
N-(2-hydroxybenzoyl)-L-phenylalanine
-
N-(2-hydroxybenzoyl)glycine
weak inhibition
N-(3-hydroxypyridine-2-carbonyl)-beta-alanine
weak inhibition
N-(3-hydroxypyridine-2-carbonyl)-D-phenylalanine
weak inhibition
N-(3-hydroxypyridine-2-carbonyl)-L-glutamic acid
-
N-(3-hydroxypyridine-2-carbonyl)-L-phenylalanine
-
N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine
N-(3-hydroxypyridine-2-carbonyl)glycine
weak inhibition
N-(pyridine-2-carbonyl)-L-phenylalanine
-
N-ethylmaleimide
-
less effective than p-chloromercuriphenylsulfonate
N-[(1-chloro-4-hydroxy-3-isoquinolinyl)carbonyl]-glycine
i.e. FG-2216, BIQ, or IOX3, an isoquinoline derivative, that inhibits BBOX and other 2-oxoglutarate dependent oxygenases through chelating active site Fe(II) and interacting with specific active site residues. Time course of Zn(II) ejection from BBOX by the inhibitors
p-aminomethylbenzoic acid
-
1.2 mmol/kg reduces the conversion of 4-dimethylaminobutyric acid to 4-dimethylamino-3-hydroxybutyric acid from 62.6% to 46.8%
p-chloromercuribenzoate
-
inactivates enzyme completely at 0.1 mM
p-chloromercuriphenylsulfonate
-
inactivates enzyme completely at 0.1 mM
Pyridine 2,4-dicarboxylate
-
-
Pyridine-2,4-dicarboxylate
-
-
structure analogues of gamma-butyrobetaine and 2-oxoglutarate
-
Succinic semialdehyde
-
-
ZnCl2
-
1 mM, complete inhibition
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium
-
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium
-
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium
-
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium
-
[3-(ethyldimethylammonio)propyl]phosphinate
-
[3-(trimethylammonio)propyl]phosphinate
-
3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate
-
3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate
i.e. mildronate, a clinically used and approved drug, but weak inhibitor. Enzyme-inhibitor interactions from structure PDB ID 3O2G
4-Trimethylammoniobutanoate
substrate inhibition at concentrations above 0.2 mM
4-Trimethylammoniobutanoate
substrate inhibition
4-Trimethylammoniobutanoate
substrate inhibition at high concentrations
4-Trimethylammoniobutanoate
substrate inhibition associated with age is observed at concentrations above 0.6 mM
ascorbate
-
irreversible inactivation during preincubation
DL-carnitine
-
uncouples the decarboxylation from the hydroxylation, mammalian enzyme
gamma-butyrobetaine
GBB, substrate inhibition at high concentrations
gamma-butyrobetaine
substrate inhibition at high concentrations. Enzyme-inhibitor interactions from structure PDB ID 3MS5
gamma-butyrobetaine
-
at concentrations above 0.2 mM
H2O2
-
-
mildronate
both a relatively weak BBOX inhibitor in vitro and a competitive substrate producing multiple products. The mode of action of mildronate may be nonselective
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
-
-
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
-
N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine
i.e AR692B
N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine
-
N-oxalylglycine
a 2-oxoglutarate mimic
N-oxalylglycine
binding structure modeling
Ni2+
-
-
Ni2+
binding structure modeling
structure analogues of gamma-butyrobetaine and 2-oxoglutarate
-
-
-
structure analogues of gamma-butyrobetaine and 2-oxoglutarate
-
-
-
additional information
identification of selective BBOX inhibitors, active against both isolated enzyme and in cells, docking study, overview. The identified template BBOX inhibitor binds to the active site iron via its carbonyl group and either its pyridine-nitrogen or C-3 hydroxyl group, the pyridine-nitrogen, C-3 hydroxyl group and side chain carboxylate are essential for binding. Examination of scaffolds with bicyclic aromatic rings, i.e. with quinoline and isoquinoline derivatives substituting for the (hydroxyl)pyridine ring reveal that quinolines have rather weak potency, while isoquinolines are relatively good inhibitors with the IC50 values in the low micromolar range. In the isoquinoline series, C-alpha side chains with the (S)-stereochemistry are preferred over those with the (R)-stereochemistry. In contrast to the pyridine series small side chains are preferred with the hydroxy-isoquinolines, with the methyl group having the best inhibitory properties
-
additional information
discovery of inhibitors of gamma-butyrobetaine hydroxylase, design, synthesis, and properties of 51 compounds, which include both gamma-butyrobetaine and mildronate analogues, structure-activity relationships, overview
-
additional information
development and application of 1H NMR GBB/2OG reporter based assays employing paramagnetic relaxation enhancement to monitor inhibitor binding to the BBOX active site, method development and evaluation, overview. The method assesses inhibitors for competitive binding with 2-oxoglutarate or gamma-butyrobetaine, or both, and is exemplified with a set of isoquinoline-based inhibitors, structure-activity relationships. Docking simulation showing possible conformational changes as a result of binding inhibitors N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine or N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)-L-tryptophan. NMR spectroscopic structures
-
additional information
-
inhibition by cyclopropyl-substituted gamma-butyrobetains
-
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0.02 - 0.412
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium
1.37
(3-carboxypropyl)(trimethyl)arsanium
pH 7.5, 23°C
1.2
(3-carboxypropyl)(trimethyl)phosphanium
pH 7.5, 23°C
0.02 - 0.623
(3R)-3-fluoro-4-(trimethylammonio)butanoate
0.012 - 0.083
(3S)-3-fluoro-4-(trimethylammonio)butanoate
0.125
2-oxo-glutarate
-
-
0.018 - 0.82
2-oxoglutarate
0.16
4-(trimethylammonio)butanoic acid
-
co-substrate: 2-oxoglutarate, pH 7.5, 25°C, NMR assay
0.04
4-Dimethylaminobutyric acid
-
in 20mM potassium phosphate buffer (pH 7.4) containing 50 mM KCl, 3mM 2-oxoglutarate, 10 mM sodium ascorbate, 0.5 mM DTT, 0.5 mM ammonium iron sulfate, 2.5 mg/ml bovine serum albumin, 0.01% (w/v) Triton X-100 and 2 mM 6-N-trimethyllysine
0.0042 - 2.474
4-Trimethylammoniobutanoate
0.029 - 2.4
gamma-butyrobetaine
additional information
additional information
-
0.02
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium
pH 7.5, temperature not specified in the publication
0.412
(2S)-3-carboxy-N-(fluoromethyl)-2-hydroxy-N,N-dimethylpropan-1-aminium
pH 7.5, temperature not specified in the publication
0.02
(3R)-3-fluoro-4-(trimethylammonio)butanoate
pH 7.5, temperature not specified in the publication
0.623
(3R)-3-fluoro-4-(trimethylammonio)butanoate
pH 7.5, temperature not specified in the publication
0.012
(3S)-3-fluoro-4-(trimethylammonio)butanoate
-
co-substrate: 2-oxoglutarate, pH 7.5, 25°C, NMR assay
0.083
(3S)-3-fluoro-4-(trimethylammonio)butanoate
-
co-substrate: 2-oxoglutarate, pH 7.5, 25°C, fluoride assay
0.018
2-oxoglutarate
-
-
0.026
2-oxoglutarate
-
co-substrate: 4-(trimethylammonio)butanoic acid, pH 7.5, 25°C, NMR assay
0.063
2-oxoglutarate
-
in 20mM potassium phosphate buffer (pH 7.4) containing 50 mM KCl, 3mM 2-oxoglutarate, 10 mM sodium ascorbate, 0.5 mM DTT, 0.5 mM ammonium iron sulfate, 2.5 mg/ml bovine serum albumin, 0.01% (w/v) Triton X-100 and 2 mM 6-N-trimethyllysine
0.1 - 0.13
2-oxoglutarate
-
gamma-butyrobetaine, values about the same for all three isozymes
0.15
2-oxoglutarate
-
co-substrate: (3S)-3-fluoro-4-(trimethylammonio)butanoate, pH 7.5, 25°C, NMR assay
0.153
2-oxoglutarate
pH 7.5, temperature not specified in the publication
0.47
2-oxoglutarate
-
co-substrate: (3S)-3-fluoro-4-(trimethylammonio)butanoate, pH 7.5, 25°C, fluoride assay
0.532
2-oxoglutarate
pH 7.5, temperature not specified in the publication
0.0042
4-Trimethylammoniobutanoate
pH 7.5, temperature not specified in the publication
0.013
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 1-day-old domestic pig, pH 7.4, 37°C
0.025
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 7-day-old domestic pig, pH 7.4, 37°C
0.026
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 56-day-old domestic pig, pH 7.4, 37°C
0.0275
4-Trimethylammoniobutanoate
pH 7.0, 37°C, recombinant enzyme
0.032
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 1-day-old domestic pig, pH 7.4, 37°C
0.037
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 56-day-old domestic pig, pH 7.4, 37°C
0.038
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 21-day-old domestic pig, pH 7.4, 37°C
0.041
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 35-day-old domestic pig, pH 7.4, 37°C
0.053
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of newborn domestic pig, pH 7.4, 37°C
0.06
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in liver of 210-day-old domestic pig, pH 7.4, 37°C
0.061
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 7-day-old domestic pig, pH 7.4, 37°C
0.063
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 21-day-old domestic pig, pH 7.4, 37°C
0.074
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 210-day-old domestic pig, pH 7.4, 37°C
0.086
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of 35-day-old domestic pig, pH 7.4, 37°C
0.119
4-Trimethylammoniobutanoate
apparent kinetic constant (Km), in kidney of newborn domestic pig, pH 7.4, 37°C
0.163
4-Trimethylammoniobutanoate
pH 7.5, temperature not specified in the publication, only the Michaelis-Menten range is fitted
1
4-Trimethylammoniobutanoate
pH 7.5, 23°C
2.474
4-Trimethylammoniobutanoate
pH 7.5, temperature not specified in the publication, the whole range is fitted
0.029
gamma-butyrobetaine
-
-
0.08
gamma-butyrobetaine
-
-
0.51
gamma-butyrobetaine
-
-
2.4
gamma-butyrobetaine
-
-
additional information
additional information
-
-
-
additional information
additional information
-
-
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
kinetic analysis, overview
-
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0.0038
(E)-4-(trimethylammonio)but-2-enoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.117
1,1,1-trimethyl-2-(2-phosphonoethyl)hydrazin-1-ium Iodide
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00049
1-(3-carboxypropyl)-1-methylpyrrolidin-1-ium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
1-(3-carboxypropyl)pyrrolidin-1-ium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.087
2-(1,1,1-trimethylhydrazin-1-ium-2-yl)ethanesulfonate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
2-(2-carboxyethyl)-1,1-diethyl-1-methylhydrazin-1-ium chloride
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.024
2-(2-carboxyethyl)-1,1-dimethyl-1-(prop-2-yn-1-yl)-hydrazin-1-ium bromide
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0102
2-(2-carboxyethyl)-1-(2-chloroethyl)-1,1-dimethylhydrazin-1-ium bromide
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00009
3-(1,1,1,2-tetramethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0031
3-(1,1,2-trimethyl-1-propylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0068
3-(1,1-dimethyl-1-vinylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
-
0.119
3-(1-allyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0072
3-(1-ethyl-1,1,2-trimethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.14
3-(1-ethyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
3-(1-isopropyl-1,1-dimethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.062
3-(2,2,2-trimethylhydrazinium propionate dihydrate)
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0028
3-(2-ethyl-1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0067
3-(ethyldimethylammonio)propane-1-sulfonate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
3-(trimethylammonio)cyclohexanecarboxylate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0017
3-(trimethylammonio)propane-1-sulfonate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.459
3-carboxy-2-chloro-N,N,N-trimethylpropan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00026
3-carboxy-N-(2-chloroethyl)-N,N-dimethylpropan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00061
3-carboxy-N-(2-fluoroethyl)-N,N-dimethylpropan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
3-hydroxy-N-(2-phenylethyl)pyridine-2-carboxamide
Homo sapiens
above, pH and temperature not specified in the publication
1
3-[1-(2-aminoethyl)-1,1-dimethylhydrazin-1-ium-2-yl]-propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
3-[1-(2-hydroxyethyl)-1,1-dimethylhydrazin-1-ium-2-yl]-propanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
-
0.0027
4-(allyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-(benzyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-(butyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00081
4-(cyclobutyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-(cyclopentyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0021
4-(cyclopropyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.388
4-(dimethylsulfonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0033
4-(ethyldimethylammonio)butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.343
4-(trimethylammonio)pentanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.015
4-([(2E)-3-carboxyprop-2-enoyl](hydroxy)amino)-N,N,N-trimethylbutan-1-aminium
Homo sapiens
pH and temperature not specified in the publication
-
1
4-[(2-hydroxyethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[(bromomethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.268
4-[(chloromethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[(cyclobutylmethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[(cyclopropylmethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[(iodomethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[(methoxymethyl)dimethylammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.1
4-[diethyl(methyl)ammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0014
4-[dimethyl(prop-2-yn-1-yl)ammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
4-[dimethyl(propyl)ammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.127
4-[dimethyl(vinyl)ammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0057
4-[isopropyl(dimethyl)ammonio]butanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
1
5-(trimethylammonio)pentanoate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.000153
AR692B
Homo sapiens
pH and temperature not specified in the publication
0.019
benzeneselenenic acid
Homo sapiens
pH 7.0, 22°C, 20 min
0.003
benzeneselenenyl bromide
Homo sapiens
pH 7.0, 22°C, 20 min
0.0029
benzeneselenenyl chloride
Homo sapiens
pH 7.0, 22°C, 20 min
0.0047
benzeneseleninic acid
Homo sapiens
pH 7.0, 22°C, 20 min
0.042
diphenyldiselane
Homo sapiens
pH 7.0, 22°C, 20 min
0.00083
ebselen
Homo sapiens
pH 7.0, 22°C, 20 min
0.0009
Isoquinoline
Homo sapiens
pH and temperature not specified in the publication
0.06
mildronate
Homo sapiens
pH and temperature not specified in the publication
1
N,N,N-trimethyl-3-(1H-tetrazol-5-yl)propan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0001
N,N,N-trimethyl-3-phosphonopropan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.026
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)-L-tryptophan
Homo sapiens
pH 7.5, temperature not specified in the publication, recombinant enzyme
0.0012 - 0.018
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
0.0012
N-(2-bromoethyl)-3-carboxy-N,N-dimethylpropan-1-aminium
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.088
N-(2-hydroxybenzoyl)-L-phenylalanine
Homo sapiens
pH and temperature not specified in the publication
0.537
N-(2-hydroxybenzoyl)glycine
Homo sapiens
pH and temperature not specified in the publication
0.522
N-(3-hydroxypyridine-2-carbonyl)-beta-alanine
Homo sapiens
pH and temperature not specified in the publication
0.15
N-(3-hydroxypyridine-2-carbonyl)-D-phenylalanine
Homo sapiens
pH and temperature not specified in the publication
0.0018
N-(3-hydroxypyridine-2-carbonyl)-L-glutamic acid
Homo sapiens
pH and temperature not specified in the publication
0.0005 - 0.002
N-(3-hydroxypyridine-2-carbonyl)-L-phenylalanine
0.0002
N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine
Homo sapiens
pH and temperature not specified in the publication
0.006 - 1
N-(3-hydroxypyridine-2-carbonyl)glycine
0.0125
N-(pyridine-2-carbonyl)-L-phenylalanine
Homo sapiens
pH and temperature not specified in the publication
0.032
N-[(1-chloro-4-hydroxy-3-isoquinolinyl)carbonyl]-glycine
Homo sapiens
pH 7.0, 22°C, 20 min
0.082
Pyridine 2,4-dicarboxylate
Homo sapiens
-
pH 7.5, 25°C
0.0079
thiram
Homo sapiens
pH 7.0, 22°C, 20 min
0.00053
[3-(ethyldimethylammonio)propyl]phosphinate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.00052
[3-(trimethylammonio)propyl]phosphinate
Homo sapiens
pH 7.0, 37°C, recombinant enzyme
0.0012
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
Homo sapiens
pH 7.5, temperature not specified in the publication, recombinant enzyme
0.018
N-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)glycine
Homo sapiens
-
pH 7.5, 25°C
0.0005
N-(3-hydroxypyridine-2-carbonyl)-L-phenylalanine
Homo sapiens
pH and temperature not specified in the publication
0.002
N-(3-hydroxypyridine-2-carbonyl)-L-phenylalanine
Homo sapiens
pH and temperature not specified in the publication
0.006
N-(3-hydroxypyridine-2-carbonyl)glycine
Homo sapiens
pH and temperature not specified in the publication
1
N-(3-hydroxypyridine-2-carbonyl)glycine
Homo sapiens
above, pH and temperature not specified in the publication
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