Information on EC 1.5.1.21 - 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase (NADPH)

for references in articles please use BRENDA:EC1.5.1.21
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.5.1.21
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RECOMMENDED NAME
GeneOntology No.
1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase (NADPH)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-pipecolate + NADP+ = 1-piperideine-2-carboxylate + NADPH + H+
show the reaction diagram
(1)
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-
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L-proline + NADP+ = 1-pyrroline-2-carboxylate + NADPH + H+
show the reaction diagram
(2)
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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-
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
lysine metabolism
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Lysine degradation
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Tropane, piperidine and pyridine alkaloid biosynthesis
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Metabolic pathways
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
52037-88-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
strain ATCC12633, gene dpkA
Uniprot
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
enzyme Pyr2C reductase is a member of the ornithine cyclodeaminase/micro-crystallin superfamily and behaves similar to DkpA
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-piperideine-2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
1-pyrroline-(4R)-hydroxy-2-carboxylate + NADPH + H+
(4R)-hydroxy-L-proline + NADP+
show the reaction diagram
-
-
-
r
1-pyrroline-2-carboxylate + NADPH + H+
L-proline + NADP+
show the reaction diagram
alpha-ketobutanoate + methylamine + NADPH
N-methyl-2-aminobutanoate + NADP+ + H2O
show the reaction diagram
10% of the rate with pyruvate
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-
?
alpha-ketohexanoate + methylamine + NADPH
N-methyl-2-aminohexanoate + NADP+ + H2O
show the reaction diagram
23% of the rate with pyruvate
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-
?
cis-3-hydroxy-L-proline + NADPH + H+
? + NADP+
show the reaction diagram
low activity
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-
r
cis-4-hydroxy-L-proline + NADPH + H+
? + NADP+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADH + H+
L-pipecolate + NAD+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
DELTA1-piperideine-2-carboxylate + NADH
L-pipecolate + NAD+
show the reaction diagram
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADH + H+
L-pipecolate + NAD+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
DELTA1-pyrroline-2-carboxylate + NADPH
L-proline + NADP+
show the reaction diagram
fluoropyruvate + methylamine + NADPH
N-methylfluoroalanine + NADP+ + H2O
show the reaction diagram
14% of the rate with pyruvate
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-
?
L-pipecolate + NADP+
1-piperideine-2-carboxylate + NADPH + H+
show the reaction diagram
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
L-proline + NADP+
1-pyrroline-2-carboxylate + NADPH + H+
show the reaction diagram
the reaction equilibrium favors the direction toward NADPH-dependent reduction
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r
phenylpyruvate + methylamine + NADPH
N-methylphenylalanine + NADP+ + H2O
show the reaction diagram
6.3% of the rate with pyruvate
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?
pyruvate + methylamine
N-methylalanine
show the reaction diagram
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-
?
trans-3-hydroxy-L-proline + NADPH + H+
? + NADP+
show the reaction diagram
moderate activity
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r
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-piperideine-2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
1-pyrroline-(4R)-hydroxy-2-carboxylate + NADPH + H+
(4R)-hydroxy-L-proline + NADP+
show the reaction diagram
Q9I492
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-
-
r
1-pyrroline-2-carboxylate + NADPH + H+
L-proline + NADP+
show the reaction diagram
cis-4-hydroxy-L-proline + NADPH + H+
? + NADP+
show the reaction diagram
Q9I492
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-
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r
DELTA1-piperideine 2-carboxylate + NADH + H+
L-pipecolate + NAD+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
DELTA1-piperideine-2-carboxylate + NADH
L-pipecolate + NAD+
show the reaction diagram
DELTA1-piperideine-2-carboxylate + NADPH
L-pipecolate + NADP+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADH + H+
L-pipecolate + NAD+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ca2+
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slight inhibition
Co2+
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almost total inhibition at 0.1 mM
Hg2+
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almost total inhibition at 0.1 mM
KCN
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slight inhibition
Mg2+
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slight inhibition
Mn2+
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almost total inhibition at 0.1 mM
NADPH
p-chloromercuribenzoate
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almost total inhibition at 0.1 mM
pyrrole-2-carboxylate
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pyrroline-2-carboxylate
inhibits the reverse reaction
Zn2+
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almost total inhibition at 0.1 mM
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dithiothreitol
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slight activation at 1 mM
EDTA
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slight activation at 1 mM
Sodium diphosphate
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slight activation at 1 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
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0.447
1-pyrroline-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.23 - 1.6
DELTA1-piperideine-2-carboxylate
0.4
DELTA1-Pyrroline-5-carboxylate
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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
0.034 - 0.14
NADP+
0.034 - 0.14
NADPH
0.28
pyroglutamate
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132
trans-3-hydroxy-L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
additional information
additional information
kinetics
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
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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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
22.5
1-piperideine-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
17.3
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
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93.2
1-pyrroline-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.065
L-pipecolate
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.185
L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.034
trans-3-hydroxy-L-proline
purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
substrate and product inhibition kinetics, overview
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.33
purified recombinant enzyme, substrates DELTA1-pyrroline-2-carboxylate and NADH
0.49
purified recombinant His-tagged enzyme, substrate trans-3-hydroxy-L-proline , pH 7.0, 30°C
0.67
purified recombinant enzyme, substrates DELTA1-piperideine-2-carboxylate and NADH
0.679
purified recombinant His-tagged enzyme, substrate L-pipecolate, pH 7.0, 30°C
1.4
purified recombinant enzyme, substrates L-pipecolate and NADP+
1.98
purified recombinant His-tagged enzyme, substrate L-proline, pH 7.0, 30°C
12.1
purified recombinant His-tagged enzyme, substrates 1-pyrroline-(4R)-hydroxy-2-carboxylate and NADH, pH 7.0, 30°C
42.3
purified recombinant His-tagged enzyme, substrate 1-piperideine-2-carboxylate, pH 7.0, 30°C; purified recombinant His-tagged enzyme, substrate 1-pyrroline-2-carboxylate, pH 7.0, 30°C
51
purified recombinant enzyme, substrates DELTA1-pyrroline-2-carboxylate and NADPH
92
purified recombinant enzyme, substrates DELTA1-piperideine-2-carboxylate and NADPH
140
substrate pyruvate, 30°C, pH 10.0
150
substrate DELTA1-piperideine-2-carboxylate, 30°C, pH 10.0
390
substrate DELTA1-pyrroline-2-carboxylate, 30°C, pH 10.0
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5
-
reduction of 1-piperideine-2-carboxylate
7
reduction reaction of 1-pyrroline-2-carboxylate and 1-piperideine-2-carboxylate
8
assay at, forward reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36000
2 * 36000, SDS-PAGE, crystallization data
50000
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70000
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78000
recombinant enzyme, gel filtration
200000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
2 * 36000, SDS-PAGE, crystallization data
homodimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
unliganded form, in complex with NADPH, and with NADPH and pyrrole-2-carboxylate. subunit consists of domain I, NADPH-binding domain II, and domain III. Identification of catalytic Asp-Ser-His triad
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 35
stable for at least 30 min, pH 7.0
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dithiothreitol, 1 mM, protects during storage
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EDTA, 1 mM, protects during storage and against heat inactivation at 50°C
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NADP+, no protection during storage
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NADPH, protection during storage
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sodium diphosphate, 1 mM, protects during storage
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very unstable during purification
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, total loss of activity of the partially purified enzyme after 8 h, loss of activity can be prevented by adding low concentrations of EDTA, sodium diphosphate, dithiothreitol or L-pipecolic acid
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme from kidney
recombinant enzyme from Escherichia coli, to homogeneity
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA sequence determination and analysis, overexpression in Escherichia coli
gene lhpD, DNA and amino acid sequence determination and analysis, phylogenetic tree, genetic organization of genes encoding enzyme involved in the trans-3-hydroxy-L-proline pathway and networks with D-lysine and D-proline, overview. Recombinant expression of His6-tagged enzyme in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
dpk disruption mutant is unable to grow on D-lysine or D-proline as sole carbon source
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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enzymatic system for synthesis of L-pipecolic acid from L-lysine by commercial L-lysine alpha-oxidase and extract of Escherichia coli producing recombinant enzyme and glucose dehydrogenase. System provides 27g/l of L-pipecolic acid in laboratory scale, with 99.7% enantiomeric excess