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1'-methylthiamine + aniline
4-methyl-5-(2-hydroxyethyl)-thiazole + 4-amino-5-(anilinomethyl)-1,2-dimethylpyrimidin-1-ium
-
22% of activity with thiamine
-
-
?
2'-ethylthiamine + aniline
4-methyl-5-(2-hydroxyethyl)-thiazole + 5-(anilinomethyl)-2-ethylpyrimidin-4-amine
-
63% of activity with thiamine
-
-
?
2-(1-hydroxyethyl)thiamine + aniline
4-methyl-2-(1-hydroxyethyl)-5-(2-hydroxyethyl)-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
92% of activity with thiamine
-
-
?
5-chloroethylthiamine + aniline
4-methyl-5-chloroethyl-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
67% of activity with thiamine
-
-
?
5-nor-thiamine + aniline
4-methyl-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
88% of activity with thiamine
-
-
?
O-(beta-D-galactosyl)thiamine + aniline
4-methyl-5-(2-hydroxyethyl-O-beta-D-galactosyl)-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
63% of activity with thiamine
-
-
?
O-benzoylthiamine + aniline
2-(4-methyl-1,3-thiazol-5-yl)ethyl benzoate + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
91% of activity with thiamine
-
-
?
O-S-diacetylthiamine + aniline
1-acetyl-4-methyl-5-(2-hydroxyethyl-O-acetyl)-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
50% of activity with thiamine
-
-
?
O-succinylthiamine + aniline
4-methyl-5-(2-hydroxyethyl-O-succinyl)-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
83% of activity with thiamine
-
-
?
pyrithiamine + aniline
2-(2-methylpyridin-3-yl)ethanol + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
72% of activity with thiamine
-
-
?
tetrahydrothiamine + aniline
?
-
84% of activity with thiamine
-
-
?
thiamine + 2-aminopyridine
?
-
-
-
-
?
thiamine + 2-hydroxyaniline
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(2-hydroxyphenyl)amine
-
-
-
-
?
thiamine + 2-mercaptobenzoic acid
?
-
-
-
-
?
thiamine + 2-mercaptoethanol
?
thiamine + 2-methylbenzeneamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(2-methylphenyl)amine
-
i.e. o-toluidine
-
-
?
thiamine + 2-pyridinecarboxylic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxypyridinium
-
i.e. alpha-picolinic acid
-
-
?
thiamine + 3-aminopyridine
?
thiamine + 3-hydroxyaniline
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(3-hydroxyphenyl)amine
-
-
-
-
?
thiamine + 3-methylbenzeneamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(3-methylphenyl)amine
-
i.e. m-toluidine
-
-
?
thiamine + 3-nitroaniline
?
-
-
-
-
?
thiamine + 3-pyridinecarboxylic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-carboxypyridinium
-
i.e. beta-picolinic acid
-
-
?
thiamine + 4-aminopyridine
?
thiamine + 4-hydroxyaniline
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(4-hydroxyphenyl)amine
-
-
-
-
?
thiamine + 4-methylbenzeneamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(4-methylphenyl)amine
-
i.e. p-toluidine
-
-
?
thiamine + 4-nitrothiophenolate
4-methyl-5-(2-hydroxyethyl)thiazole + 2-methyl-5[[(4-nitrophenyl)sulfanyl]methyl]pyrimidin-4-amine
no activity with thiaminase II
-
-
?
thiamine + 4-nitrothiophenolate
?
-
-
-
?
thiamine + 4-pyridinecarboxylic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-carboxypyridinium
-
i.e. gamma-picolinic acid
-
-
?
thiamine + 6-aminohexanoic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 6-[[(4-amino-2-methylpyrimidin-5-yl)methyl]amino]hexanoic acid
-
-
-
-
?
thiamine + adenine
?
-
-
-
-
?
thiamine + alpha-picoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]alpha-picolinium
-
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
thiamine + beta-picoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]beta-picolinium
-
-
-
-
?
thiamine + cysteine
?
-
-
-
-
?
thiamine + gamma-picoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]gamma-picolinium
-
-
-
-
?
thiamine + hydroxyproline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]4-hydroxypyrrolidine-2-carboxylic acid
thiamine + imidazole
4-methyl-5-(2-hydroxyethyl)-thiazole + 5-(1H-imidazol-1-yl-methyl)-2-methylpyrimidin-4-amine
thiamine + L-cysteine
4-methyl-5-(2-hydroxyethyl)-thiazole + 2-[[(4-amino-2-ethylpyrimidin-5-yl)methyl]amino]-3-mercaptopropanoic acid
thiamine + L-lysine
?
-
-
-
-
?
thiamine + m-aminobenzoic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 3-[[(4-amino-2-methylpyrimidin-5-yl)methyl]amino]benzoic acid
-
-
-
-
?
thiamine + m-phenylene diamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(3-aminophenyl)amine
-
-
-
-
?
thiamine + methylamine
?
-
-
-
-
?
thiamine + nicotinic acid
?
thiamine + o-aminobenzoic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 2-[[(4-amino-2-methylpyrimidin-5-yl)methyl]amino]benzoic acid
-
-
-
-
?
thiamine + o-phenylene diamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(2-aminophenyl)amine
-
-
-
-
?
thiamine + p-aminobenzoic acid
4-methyl-5-(2-hydroxyethyl)-thiazole + 4-[[(4-amino-2-methylpyrimidin-5-yl)methyl]amino]benzoic acid
-
-
-
-
?
thiamine + p-phenylene diamine
4-methyl-5-(2-hydroxyethyl)-thiazole + [(4-amino-2-methylpyrimidin-5-yl)methyl]-N-(4-aminophenyl)amine
-
-
-
-
?
thiamine + proline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyrrolidine-2-carboxylic acid
thiamine + pyridine
1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyridinium + 4-methyl-5-(2-hydroxyethyl)thiazole
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
thiamine + pyridoxine
?
-
-
-
-
?
thiamine + quinoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]quinolinium
thiamine + sulfanilamide
?
-
-
-
-
?
thiamine + sulfanilic acid
?
-
-
-
-
?
thiamine + Tris
?
-
-
-
-
?
thiamine + veratrylamine
bis-(4-amino-2-methyl)pyrimidinyl-3,4-dimethoxybenzylamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
the reaction can occur without base substrate
-
?
thiamine disulfide + aniline
?
-
26% of activity with thiamine
-
-
?
thiamine phosphate + aniline
2-(4-methyl-1,3-thiazol-5-yl)ethyl dihydrogenphosphate + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
64% of activity with thiamine
-
-
?
thiothiamine + aniline
4-methyl-5-(2-hydroxyethyl)-2-thio-thiazole + 5-(anilinomethyl)-2-methylpyrimidin-4-amine
-
12% of activity with thiamine
-
-
?
additional information
?
-
thiamine

?
-
there is activity without base substrate
-
-
?
thiamine
?
there is degradation of thiamine without a base substrate, possibly the ring-opened form of thiamine functions as the nucleophile
-
-
?
thiamine
?
-
there is activity without base substrate
-
-
?
thiamine + 2-mercaptoethanol

?
-
-
-
-
?
thiamine + 2-mercaptoethanol
?
-
63% of activity with aniline
-
-
?
thiamine + 2-mercaptoethanol
?
-
-
-
-
?
thiamine + 3-aminopyridine

?
-
-
-
-
?
thiamine + 3-aminopyridine
?
-
-
-
-
?
thiamine + 4-aminopyridine

?
-
-
-
-
?
thiamine + 4-aminopyridine
?
-
-
-
-
?
thiamine + aniline

5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
activity found
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
taken as 100% of activity of purified enzyme
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
one molecule of thiamine is cleaved releasing one molecule of methylhydroxyethylthiazole for one molecule of enzyme
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
activity found
-
?
thiamine + aniline
5-(anilinomethyl)-2-methylpyrimidin-4-amine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + hydroxyproline

4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]4-hydroxypyrrolidine-2-carboxylic acid
-
-
-
-
?
thiamine + hydroxyproline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]4-hydroxypyrrolidine-2-carboxylic acid
-
-
-
-
?
thiamine + imidazole

4-methyl-5-(2-hydroxyethyl)-thiazole + 5-(1H-imidazol-1-yl-methyl)-2-methylpyrimidin-4-amine
-
24% of activity with aniline
-
-
?
thiamine + imidazole
4-methyl-5-(2-hydroxyethyl)-thiazole + 5-(1H-imidazol-1-yl-methyl)-2-methylpyrimidin-4-amine
-
-
-
-
?
thiamine + L-cysteine

4-methyl-5-(2-hydroxyethyl)-thiazole + 2-[[(4-amino-2-ethylpyrimidin-5-yl)methyl]amino]-3-mercaptopropanoic acid
-
50% of activity with aniline
-
-
?
thiamine + L-cysteine
4-methyl-5-(2-hydroxyethyl)-thiazole + 2-[[(4-amino-2-ethylpyrimidin-5-yl)methyl]amino]-3-mercaptopropanoic acid
-
-
-
-
?
thiamine + nicotinic acid

?
-
-
-
-
?
thiamine + nicotinic acid
?
-
-
-
-
?
thiamine + nicotinic acid
?
-
-
-
-
?
thiamine + proline

4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyrrolidine-2-carboxylic acid
-
-
-
-
?
thiamine + proline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyrrolidine-2-carboxylic acid
-
-
-
-
?
thiamine + pyridine

1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyridinium + 4-methyl-5-(2-hydroxyethyl)thiazole
-
-
-
-
?
thiamine + pyridine
1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyridinium + 4-methyl-5-(2-hydroxyethyl)thiazole
-
the reaction rate measured by pyridine as the second substrate is three times higher in pI 7-9 enzymes compared with pI 5.7 enzyme
-
-
?
thiamine + pyridine

heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
best substrate with aniline
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + pyridine
heteropyrithiamine + 4-methyl-5-(2-hydroxyethyl)-thiazole
-
-
-
?
thiamine + quinoline

4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]quinolinium
-
-
-
-
?
thiamine + quinoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]quinolinium
-
-
-
-
?
thiamine + quinoline
4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]quinolinium
-
-
-
-
?
additional information

?
-
-
no activity with 4'-deaminothiamine and 4'-oxythiamine suggest that 4'-amino group is essential for enzyme activity
-
-
?
additional information
?
-
-
primary substrates inactivate the enzyme at 0.006 mM and secondary substrates or acceptor bases reactivate the enzyme at 10 mM, each substrate at high concentrations eliminates the inactivation of the other substrate
-
-
?
additional information
?
-
-
primary substrates inactivate the enzyme at 0.006 mM and secondary substrates or acceptor bases reactivate the enzyme at 10 mM, each substrate at high concentrations eliminates the inactivation of the other substrate
-
-
?
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4-Amino-5-(anilinomethyl)-6-chloro-2-methylpyrimidine
-
complete irreversible inhibition 2 times faster than 4-amino-6-chloro-2-methylpyrimidine
4-Amino-6-chloro-2-methylpyrimidine
Ag+
-
100% inhibition at 1 mM
aromatic amines
-
inhibited by or without effect
-
Cd2+
-
the degree of cadmium inhibition, when aniline is the cosubstrate, shows obvious differences between pI isozymes
Dimethialium
-
inactivation at 0.006 mM
heterocyclic amines
-
-
-
thiamine diphosphate
-
inactivation at 0.006 mM
4-Amino-6-chloro-2-methylpyrimidine

-
complete irreversible inhibition, activity protected by thiamine and quinolone
4-Amino-6-chloro-2-methylpyrimidine
inhibitory
4-Amino-6-chloro-2-methylpyrimidine
this suicide substrate is linked to Cys113 of the enzyme
4-aminopyrimidines

-
mostly inhibitory
4-aminopyrimidines
-
mostly inhibitory
aniline

-
highly inhibitory above 2.4 mM
aniline
-
inactivation at 0.006 mM; reactivation at 2 mM
Cu2+

-
different inhibitory effects at 1 mM
Cu2+
-
different inhibitory effects at 1 mM
Cu2+
Celosia crista
-
different inhibitory effects at 1 mM
Cu2+
Dicranopteris sp.
-
different inhibitory effects at 1 mM
Cu2+
-
50% of inhibition at 1 mM
Cu2+
-
different inhibitory effects at 1 mM
Cu2+
-
different inhibitory effects at 1 mM
Fe2+

-
different inhibitory effects at 1 mM
Fe2+
-
different inhibitory effects at 1 mM
Fe2+
Celosia crista
-
different inhibitory effects at 1 mM
Fe2+
Dicranopteris sp.
-
different inhibitory effects at 1 mM
Fe2+
-
70% of inhibition at 1 mM
Fe2+
-
different inhibitory effects at 1 mM
Fe2+
-
different inhibitory effects at 1 mM
Heteropyrithiamine

-
inhibitory at 0.006 mM
Heteropyrithiamine
-
inactivation at 0.006 mM that is restored by pyridine at 25 mM and inhibition of restoration of activity by pyridine at 1 mM
HgCl2

-
potent inhibitor at 0.001 mM
HgCl2
-
potent inhibitor at 0.001 mM
HgCl2
-
potent inhibitor at 0.001 mM
HgCl2
-
potent inhibitor at 0.001 mM
Mersalyl acid

-
potent inhibitor at 0.001 mM
Mersalyl acid
-
potent inhibitor at 0.001 mM
Mersalyl acid
-
potent inhibitor at 0.001 mM
Mersalyl acid
-
potent inhibitor at 0.001 mM
Mn2+

-
different inhibitory effects at 1 mM
Mn2+
-
different inhibitory effects at 1 mM
Mn2+
Celosia crista
-
different inhibitory effects at 1 mM
Mn2+
Dicranopteris sp.
-
different inhibitory effects at 1 mM
Mn2+
-
different inhibitory effects at 1 mM
Mn2+
-
different inhibitory effects at 1 mM
Mn2+
-
different inhibitory effects at 1 mM
p-chloromercuribenzoate

-
complete inhibition at 0.001 mM
p-chloromercuribenzoate
-
complete inhibition at 0.001 mM
p-chloromercuribenzoate
-
50% of inhibition at 0.2 mM and inhibits reactivation by pyridine
p-chloromercuribenzoate
-
complete inhibition at 0.001 mM
p-chloromercuribenzoate
-
complete inhibition at 0.001 mM
thiamine

-
slightly inhibitory above 0.035 mM
thiamine
-
reversible inactivation above 0.0003 mM
thiamine
-
inactivation at 0.006 mM
thiamine
-
inactivation is proportional to thiamine concentration and the thiamine/enzyme ratio is 1 mol/1 mol
additional information

-
not inhibited by EDTA
-
additional information
-
chloramphenicol does not affect activity suggesting that the enzyme has an inactive form
-
additional information
-
primary substrates inactivate the enzyme at 0.006 mM, the lost activity can be restored by incubation at 37°C for 60 min after dialysis or by incubation with secondary substrates or acceptor bases, each substrate at high concentrations abolishes the inactivation of the other substrate
-
additional information
-
acidic conditions prevent inactivation but low pH does not restore activity after inactivation, quaternary nitrogen linked to a substituted pyrimidine ring through a methylene bridge is shared by compounds that inactivates the enzyme, inactivation alters either the net charge or the structure of the protein or both
-
additional information
-
4-amino-2-methyl pyrimidine does not inactivate nor competitively inhibits the enzyme
-
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