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Information on EC 1.5.1.21 - 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase (NADPH)
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1.5.1.21 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase (NADPH)IUBMB Comments
The enzyme is involved in the catabolism of D-lysine and D-proline in bacteria that belong to the Pseudomonas genus. In contrast to EC 1.5.1.1, 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase [NAD(P)H], which shows similar activity with NADPH and NADH, this enzyme is specific for NADPH.
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
pip2cr, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,2-didehydropipecolate reductase
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1,2-didehydropipecolic reductase
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CRYM
DELTA1-piperideine-2-carboxylate reductase
DELTA1-piperideine-2-carboxylate/DELTA1-pyrroline-2-carboxylate reductase
EC 1.5.1.14
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formerly
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ketimine reductase
L-pipecolate:NADP+ 2-oxidoreductase
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mu-crystallin
P2C reductase
P2C/Pyr2C reductase
Pip2CR
reductase, DELTA 1-piperideine-2-carboxylate
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DELTA1-piperideine-2-carboxylate reductase
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DELTA1-piperideine-2-carboxylate/DELTA1-pyrroline-2-carboxylate reductase
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DELTA1-piperideine-2-carboxylate/DELTA1-pyrroline-2-carboxylate reductase
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P2C reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-pipecolate + NADP+ = 1-piperideine-2-carboxylate + NADPH + H+
(1)
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L-proline + NADP+ = 1-pyrroline-2-carboxylate + NADPH + H+
(2)
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
L-pipecolate/L-proline:NADP+ 2-oxidoreductase
The enzyme is involved in the catabolism of D-lysine and D-proline in bacteria that belong to the Pseudomonas genus. In contrast to EC 1.5.1.1, 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase [NAD(P)H], which shows similar activity with NADPH and NADH, this enzyme is specific for NADPH.
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CAS REGISTRY NUMBER
COMMENTARY
52037-88-4
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-pyrroline-(4R)-hydroxy-2-carboxylate + NADPH + H+
(4R)-hydroxy-L-proline + NADP+
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r
alpha-ketobutanoate + methylamine + NADPH
N-methyl-2-aminobutanoate + NADP+ + H2O
10% of the rate with pyruvate
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?
alpha-ketohexanoate + methylamine + NADPH
N-methyl-2-aminohexanoate + NADP+ + H2O
23% of the rate with pyruvate
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?
cis-3-hydroxy-L-proline + NADPH + H+
? + NADP+
low activity
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r
DELTA1-pyrroline-5-carboxylate + NADPH + H+
?
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very little activity
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r
fluoropyruvate + methylamine + NADPH
N-methylfluoroalanine + NADP+ + H2O
14% of the rate with pyruvate
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?
L-pipecolate + NADP+
1-piperideine-2-carboxylate + NADPH + H+
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
L-proline + NADP+
1-pyrroline-2-carboxylate + NADPH + H+
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
phenylpyruvate + methylamine + NADPH
N-methylphenylalanine + NADP+ + H2O
6.3% of the rate with pyruvate
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?
trans-3-hydroxy-L-proline + NADPH + H+
? + NADP+
moderate activity
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r
1-piperideine-2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
1-piperideine-2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
1-pyrroline-2-carboxylate + NADPH + H+
L-proline + NADP+
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r
1-pyrroline-2-carboxylate + NADPH + H+
L-proline + NADP+
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
cis-4-hydroxy-L-proline + NADPH + H+
? + NADP+
low activity
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
the equilibrium position lies far toward formation of the six-membered ring structure L-pipecolate at neutral pH
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?
DELTA1-piperideine-2-carboxylate + NADH
L-pipecolate + NAD+
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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ir
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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D-lysine metabolism
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
NADH is a poor electron donor, lower activity in the reverse reaction direction
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r
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
NADH is a poor electron donor, lower activity in the reverse reaction direction
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r
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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?
DELTA1-pyrroline-2-carboxylate + NADPH
L-proline + NADP+
NADH is a poor electron donor, lower activity in the reverse reaction direction
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r
DELTA1-pyrroline-2-carboxylate + NADPH
L-proline + NADP+
NADH is a poor electron donor, lower activity in the reverse reaction direction
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r
additional information
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the same enzyme catalyzes the reduction of both DELTA1-piperideine-2-carboxylate and DELTA1-pyrrolidine-2-carboxylate, but is unable to catalyze the reduction of DELTA1-pyrroline-5-carboxylate and DELTA1-piperideine-6-carboxylate, which may be regarded as double bond positional isomers of DELTA1-piperideine-2-carboxylate and DELTA1-pyrrolidine-2-carboxylate, respectively
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?
additional information
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PaLhpD shows 32.8%, 14.4% and 12.2% activity for trans-3-hydroxy-L-proline, cis-4-hydroxy-L-proline, and cis-3-hydroxy-L-proline as a percent of L-proline in the oxidation reaction, respectively. Both L-proline and L-pipecolate undergo NADP+-dependent oxidization, but their kcat/Km values are 500 and 350fold lower than those with 1-pyrroline-2-carboxylate and 1-piperideine-2-carboxylate, respectively. No activity with trans-4-hydroxy-D-proline, D-proline, cis-4-hydroxy-D-proline, and cis-3-hydroxy-D-proline, poor activity with trans-4-hydroxy-L-proline
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?
additional information
?
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poor substrates: DELTA1-pyrroline-5-carboxylate, pyroglutamate
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?
additional information
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
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?
additional information
?
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
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?
additional information
?
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substrate specificity, enzyme shows no malate or lactate dehydrogenase activity
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?
additional information
?
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substrate specificity, enzyme shows no malate or lactate dehydrogenase activity
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?
additional information
?
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
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?
additional information
?
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substrate specificity, enzyme shows no malate or lactate dehydrogenase activity
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?
additional information
?
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no substrate: alpha-ketovalerate, ammonia
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-pyrroline-(4R)-hydroxy-2-carboxylate + NADPH + H+
(4R)-hydroxy-L-proline + NADP+
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r
1-piperideine-2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
1-pyrroline-2-carboxylate + NADPH + H+
L-proline + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
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r
DELTA1-piperideine-2-carboxylate + NADH
L-pipecolate + NAD+
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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D-lysine metabolism
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?
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
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?
additional information
?
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the same enzyme catalyzes the reduction of both DELTA1-piperideine-2-carboxylate and DELTA1-pyrrolidine-2-carboxylate, but is unable to catalyze the reduction of DELTA1-pyrroline-5-carboxylate and DELTA1-piperideine-6-carboxylate, which may be regarded as double bond positional isomers of DELTA1-piperideine-2-carboxylate and DELTA1-pyrrolidine-2-carboxylate, respectively
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?
additional information
?
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
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?
additional information
?
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
-
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?
additional information
?
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enzyme is involved in the catabolism of D-lysine and D-proline, pathway overview
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
specific activity with NADPH is 88fold higher than with NADH. Preferrence of NADPH over NADH is explained by cofactor binding site architecture
NADPH
specific activity with NADPH is 88fold higher than with NADH. Preferrence of NADPH over NADH is explained by cofactor binding site architecture
additional information
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the enzyme purified from bovine cerebellum exhibits a marked preference for NADPH over NADH with substrate 1-piperideine-2-carboxylate
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additional information
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the enzyme purified from porcine kidney exhibits a marked preference for NADPH over NADH
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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the enzyme activity is potently inhibited by thyroid hormones
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additional information
the enzyme activity is potently inhibited by thyroid hormones
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additional information
the enzyme activity is potently inhibited by thyroid hormones
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additional information
the enzyme activity is potently inhibited by thyroid hormones
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additional information
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no effect: 0.1 mM L-cysteine, 0.1 mM iodoacetate
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additional information
the enzyme activity is potently inhibited by thyroid hormones
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additional information
the enzyme activity is potently inhibited by thyroid hormones
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.57
1-piperideine-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.835
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.447
1-pyrroline-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
34.8
L-pipecolate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
18.5
L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
132
trans-3-hydroxy-L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
1.4
DELTA1-piperideine-2-carboxylate
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at pH 6.5 temperature not specified in the publication
1.6
DELTA1-piperideine-2-carboxylate
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at pH 6.5, temperature not specified in the publication
0.034
NADPH
pH 8.0, 35°C, with substrate DELTA1-pyrroline-2-carboxylate
0.14
NADPH
pH 8.0, 35°C, with substrate DELTA1-piperideine-2-carboxylate
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
35.3
1-piperideine-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
14.5
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
41.67
1-pyrroline-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
2.25
L-pipecolate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
3.42
L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
4.53
trans-3-hydroxy-L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
22.5
1-piperideine-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C