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thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+

classical ping-pong mechanism
-
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
classical ping-pong mechanism
-
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
in silico docking of various ligands into the active site of the X-ray structure of the enzyme suggests an unusual catalytic mechanism involving an arginine residue as a proton donor
-
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
in silico docking of various ligands into the active site of the X-ray structure of the enzyme suggests an unusual catalytic mechanism involving an arginine residue as a proton donor
-
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
in silico docking of various ligands into the active site of the X-ray structure of the enzyme suggests an unusual catalytic mechanism involving an arginine residue as a proton donor, proposed mechanism for the reaction catalyzed by ketimine reductase/CRYM, overview
-
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
the enzyme binds 2-oxo acids, such as pyruvate, in solution, and catalyzes the formation of N-alkyl-amino acids from alkylamines and 2-oxo acids via reduction of imine intermediates. Mechanistically, ketimine reductase/CRYM acts as a classical imine reductase
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
proposed catalytic mechanism of ketimine reductase
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
proposed catalytic mechanism of ketimine reductase
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
-
-
-
-
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1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
aminoethyl cysteine ketimine + NADPH + H+
thiomorpholine-3-carboxylate
-
-
-
?
cystathionine ketimine + NADH
cyclothionine + NAD+
cystathionine ketimine + NADPH
cyclothionine + NADP+
DELTA1-piperideine 2-carboxylate + NADH
? + NAD+
DELTA1-piperideine 2-carboxylate + NADPH
? + NADP+
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
glyocylate + methylamine + NADPH + H+
sarcosine + NADP+
-
-
-
?
lanthionine ketimine + NADH
1,4-thiomorpholine 3,5-dicarboxylic acid + NAD+
lanthionine ketimine + NADPH
1,4-thiomorpholine 3,5-dicarboxylic acid + NADP+
lanthionine ketimine + NADPH + H+
thiomorpholine-3,5-dicarboxylate
phenylpyruvate + methylamine + NADPH + H+
N-methyl-L-phenylalanine + NADP+
-
-
-
?
pyruvate + ethylamine + NADPH + H+
N-ethyl-L-alanine + NADP+
-
-
-
?
pyruvate + methylamine + NADPH + H+
N-methyl-L-alanine + NADP+
-
-
-
?
pyruvate + NH3 + NADPH + H+
L-alanine + NADP+
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
S-aminoethylcysteine ketimine + NADH
1,4-thiomorpholine 3-carboxylic acid + NAD+
S-aminoethylcysteine ketimine + NADPH
1,4-thiomorpholine 3-carboxylic acid + NADP+
thiomorpholine 3-carboxylate + NAD(P)+
3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
additional information
?
-
cystathionine ketimine + NADH

cyclothionine + NAD+
-
-
-
-
?
cystathionine ketimine + NADH
cyclothionine + NAD+
-
-
-
ir
cystathionine ketimine + NADPH

cyclothionine + NADP+
-
-
-
-
?
cystathionine ketimine + NADPH
cyclothionine + NADP+
-
-
-
ir
DELTA1-piperideine 2-carboxylate + NADH

? + NAD+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADH
? + NAD+
-
-
-
-
ir
DELTA1-piperideine 2-carboxylate + NADPH

? + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH
? + NADP+
-
-
-
-
ir
DELTA1-piperideine 2-carboxylate + NADPH + H+

L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+

L-proline + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+

? + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
-
-
-
-
?
lanthionine ketimine + NADH

1,4-thiomorpholine 3,5-dicarboxylic acid + NAD+
-
-
-
-
?
lanthionine ketimine + NADH
1,4-thiomorpholine 3,5-dicarboxylic acid + NAD+
-
-
-
ir
lanthionine ketimine + NADPH

1,4-thiomorpholine 3,5-dicarboxylic acid + NADP+
-
-
-
-
?
lanthionine ketimine + NADPH
1,4-thiomorpholine 3,5-dicarboxylic acid + NADP+
-
-
-
ir
lanthionine ketimine + NADPH + H+

thiomorpholine-3,5-dicarboxylate
-
-
-
?
lanthionine ketimine + NADPH + H+
thiomorpholine-3,5-dicarboxylate
low activity
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+

1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-aminoethylcysteine ketimine + NADH

1,4-thiomorpholine 3-carboxylic acid + NAD+
-
-
-
-
?
S-aminoethylcysteine ketimine + NADH
1,4-thiomorpholine 3-carboxylic acid + NAD+
-
-
L-enantiomer
ir
S-aminoethylcysteine ketimine + NADPH

1,4-thiomorpholine 3-carboxylic acid + NADP+
-
-
-
-
?
S-aminoethylcysteine ketimine + NADPH
1,4-thiomorpholine 3-carboxylic acid + NADP+
-
-
-
ir
thiomorpholine 3-carboxylate + NAD(P)+

3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
-
-
-
?
thiomorpholine 3-carboxylate + NAD(P)+
3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
-
-
-
?
additional information

?
-
-
the non-sulfur substrates exist in equilibrium with open chain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
-
the non-sulfur substrates exist in equilibrium with open chain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
human ketimine reductase/CRYM can utilize alkylamines (such as methylamine and ethylamine) and 2-oxo acids (such as pyruvate and phenylpyruvate) as enzyme substrates. Analysis of reaction intermediates, overview. Mammalian ketimine reductase reaction is known to be enantiospecific and only the L-enantiomer product is formed in vivo. A ketimine reductase/CRYM-catalyzed reaction at neutral pH in the reverse direction is not determined
-
-
?
additional information
?
-
-
in silico docking of substrates and inhibitors using ketimine reductase/CRYM cyrstal structure, PDB ID 4BVA, overview
-
-
?
additional information
?
-
reciprocal relationship between thyroid hormone binding and DELTA1-piperideine-2-carboxylate (P2C) binding to ketimine reductase
-
-
-
additional information
?
-
purified recombinant human CRYM possesses substantial KR activity. Ketimine reductase is a typical imine reductase. Substrate specificity of recombinant human ketimine reductase (KR) toward DELTA1-piperideine-2-carboxylate (P2CR) and various noncyclized imine intermediates, overview. N-methyl-L-alanine is produced when human KR is incubated in the presence of methylamine, NADPH and pyruvate. Human KR catalyzes the reductive alkylamination of phenylpyruvate and glyoxylate in the presence of methylamine
-
-
-
additional information
?
-
-
the non-sulfur substrates exist in equilibrium with openchain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
reciprocal relationship between thyroid hormone binding and DELTA1-piperideine-2-carboxylate (P2C) binding to ketimine reductase
-
-
-
additional information
?
-
purified recombinant human CRYM possesses substantial KR activity. Ketimine reductase is a typical imine reductase
-
-
-
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1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
aminoethyl cysteine ketimine + NADPH + H+
thiomorpholine-3-carboxylate
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
lanthionine ketimine + NADPH + H+
thiomorpholine-3,5-dicarboxylate
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
thiomorpholine 3-carboxylate + NAD(P)+
3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
additional information
?
-
DELTA1-piperideine 2-carboxylate + NADPH + H+

L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+

L-proline + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
-
-
-
-
?
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+

? + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
-
-
-
-
?
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+

1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
-
-
-
-
?
thiomorpholine 3-carboxylate + NAD(P)+

3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
-
-
-
?
thiomorpholine 3-carboxylate + NAD(P)+
3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
-
-
-
?
additional information

?
-
-
the non-sulfur substrates exist in equilibrium with open chain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
-
the non-sulfur substrates exist in equilibrium with open chain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
reciprocal relationship between thyroid hormone binding and DELTA1-piperideine-2-carboxylate (P2C) binding to ketimine reductase
-
-
-
additional information
?
-
-
the non-sulfur substrates exist in equilibrium with openchain forms at low acidic pH. At neutral pH, they exist predominantly as the enzymatically favorable cyclic ketimine form (in which the ring double bond is in the C=N form), while sulfur-containing cyclic ketimine substrates exist predominantly as the enzymatically unfavorable enamine form (in which the ring double bond is in the C=C form) at neutral pH
-
-
?
additional information
?
-
reciprocal relationship between thyroid hormone binding and DELTA1-piperideine-2-carboxylate (P2C) binding to ketimine reductase
-
-
-
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3,3',5'-L-triiodothyronine
3,5,3'-L-triiodothyronine
3,5-diiodothyronine
-
competitive inhibition
3,5-L-diiodothyronine
-
-
4,5-dibromopyrrole-2-carboxylate
DELTA1-piperideine 2-carboxylate
-
substrate inhibition
S-(2-aminoethyl)-L-cysteine ketimine
-
substrate inhibition
Triton X-100
-
irreversible inactivation
3,3',5'-L-triiodothyronine

-
competitive inhibition
3,3',5'-L-triiodothyronine
-
3,5,3'-L-triiodothyronine

-
competitive inhibition
3,5,3'-L-triiodothyronine
-
3,5,3'-triiodothyronine

-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3
3,5,3'-triiodothyronine
-
-
3,5,3'-triiodothyronine
-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3
3,5,3'-triiodothyronine
the enzyme shows strong binding to 3,5,3'-triiodothyronine (T3), the active form of thyroxine
3,5,3'-triiodothyronine
-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3
3,5,3'-triiodothyronine
-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3
3,5,3'-triiodothyronine
-
-
3,5,3'-triiodothyronine
-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3, especially at neutral pH, reversible inhibition
3,5,3'-triiodothyronine
-
the ketimine reductase activity of CRYM is strongly inhibited by the thyroid hormone T3
3,5-diiodo-L-tyrosine

-
low competitive inhibition
4,5-dibromopyrrole-2-carboxylate

-
-
4,5-dibromopyrrole-2-carboxylate
-
-
4,5-dibromopyrrole-2-carboxylate
-
-
L-thyroxine

-
competitive inhibition
L-tyrosine

-
competitive inhibition
picolinate

-
-
picolinate
-
competitive inhibition, picolinate is a much poorer inhibitor than pyrrole-2-carboxylate because it does not possess a ring -NH and relies on a relatively weak ring interaction
pyrrole-2-carboxylate

-
-
pyrrole-2-carboxylate
-
competitive inhibition, pyrrole-2-carboxylate is an effective inhibitor of ketimine reductase/CRYM mainly as a result of the -NH hydrogen bonding to an active site residue
pyrrole-2-carboxylate
-
-
additional information

-
in silico docking of substrates and inhibitors using ketimine reductase/CRYM cyrstal structure, PDB ID 4BVA, overview
-
additional information
the P2C reductase activity is potently inhibited by thyroid hormones, thyroid hormones and analogues docked into the active site of the crystal structure of human KR, overview
-
additional information
the P2C reductase activity is potently inhibited by thyroid hormones
-
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