Information on EC 1.5.1.1 - 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase [NAD(P)H]

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.5.1.1
-
RECOMMENDED NAME
GeneOntology No.
1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase [NAD(P)H]
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-pipecolate + NAD(P)+ = 1-piperideine-2-carboxylate + NAD(P)H + H+
show the reaction diagram
(1)
-
-
-
L-proline + NAD(P)+ = 1-pyrroline-2-carboxylate + NAD(P)H + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
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-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
L-lysine degradation II (L-pipecolate pathway)
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-
L-lysine degradation V
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L-pipecolate biosynthesis
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L-proline biosynthesis IV
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trans-3-hydroxy-L-proline degradation
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proline metabolism
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Lysine degradation
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Arginine and proline metabolism
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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:NAD(P)+ 2-oxidoreductase
The enzymes, characterized from the bacterium Azospirillum brasilense, is involved in trans-3-hydroxy-L-proline metabolism. In contrast to EC 1.5.1.21, 1-piperideine-2-carboxylate/1-pyrroline-2-carboxylate reductase (NADPH), which is specific for NADPH, this enzyme shows similar activity with NADPH and NADH.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-16-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
beagle
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-
Manually annotated by BRENDA team
Cercocebus sp.
monkey
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
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, different from known dpkA protein, and there are several significant differences in the enzymatic properties between Azospirillum brasilense and another bacteria: substrate and coenzyme specificities, phylogenetic analysis
malfunction
disruption of LhpI gene from Azospirillum brasilense leads to loss of growth on trans-3-hydroxy-L-proline (T3LHyp), D-proline and D-lysine
metabolism
the enzyme is involved in the trans-3-hydroxy-L-proline pathway and the metabolic networks with D-lysine and D-proline, overview. The trans-3-hydroxy-L-proline pathway is not linked to trans-4-hydroxy-L-proline and L-proline metabolism
physiological function
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 + NAD(P)H + H+
L-pipecolate + NAD(P)+
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 + NAD(P)H + H+
L-proline + NAD(P)+
show the reaction diagram
cis-3-hydroxy-L-proline + NADP+
? + NADPH + H+
show the reaction diagram
low activity
-
-
r
cis-4-hydroxy-L-proline + NADP+
? + NADPH + H+
show the reaction diagram
low activity
-
-
r
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
-
-
-
-
?
DELTA1-piperidine-2-carboxylate + NAD(P)H
L-pipecolic acid + NAD(P)+
show the reaction diagram
DELTA1-pyrroline-2-carboxylate + NAD(P)H
L-proline + NAD(P)+
show the reaction diagram
L-pipecolate + NAD(P)+
1-piperideine-2-carboxylate + NAD(P)H + H+
show the reaction diagram
-
-
-
r
L-pipecolic acid + NAD(P)+
DELTA1-piperidine-2-carboxylate + NAD(P)H
show the reaction diagram
-
at 26% of the rate with L-proline
-
-
r
L-proline + NAD(P)+
1-pyrroline-2-carboxylate + NAD(P)H + H+
show the reaction diagram
-
-
-
r
L-proline + NAD(P)+
DELTA1-pyrroline-2-carboxylate + NAD(P)H + H+
show the reaction diagram
-
-
-
-
r
trans-4-hydroxy-L-proline + NADP+
? + NADPH + H+
show the reaction diagram
low activity
-
-
r
additional information
?
-
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 + NAD(P)H + H+
L-pipecolate + NAD(P)+
show the reaction diagram
1-pyrroline-2-carboxylate + NAD(P)H + H+
L-proline + NAD(P)+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
-
-
-
-
?
DELTA1-piperidine-2-carboxylate + NAD(P)H
L-pipecolic acid + NAD(P)+
show the reaction diagram
DELTA1-pyrroline-2-carboxylate + NAD(P)H
L-proline + NAD(P)+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
additional information
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
N-formyl-L-methionine
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non competitive inhibition, EDTA decreases the inhibition rate
additional information
-
not: p-hydroxymercuribenzoate
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.474 - 0.6
1-piperideine-2-carboxylate
0.491
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 6.5, 30C
-
0.628 - 0.837
1-pyrroline-2-carboxylate
0.06 - 0.21
DELTA1-piperidine-2-carboxylate
0.082 - 0.86
DELTA1-pyrroline-2-carboxylate
80
L-pipecolate
purified recombinant His-tagged enzyme, with NADP+, pH 6.5, 30C
18.3 - 18.8
L-proline
0.02 - 0.43
NADH
0.038
NADPH
-
+ DELTA1-pyrroline-2-carboxylate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
161.5 - 166
1-piperideine-2-carboxylate
10.35
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 6.5, 30C
-
523 - 615
1-pyrroline-2-carboxylate
0.0213
L-pipecolate
purified recombinant His-tagged enzyme, with NADP+, pH 6.5, 30C
0.0069 - 1.09
L-proline
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
269 - 350
1-piperideine-2-carboxylate
21.1
1-pyrroline-(4R)-hydroxy-2-carboxylate
purified recombinant His-tagged enzyme, with NADPH, pH 6.5, 30C
-
735 - 833
1-pyrroline-2-carboxylate
0.00027
L-pipecolate
purified recombinant His-tagged enzyme, with NADP+, pH 6.5, 30C
0.00037 - 0.06
L-proline
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.18
N-formyl-L-methionine
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0005
purified recombinant His-tagged enzyme, substrates L-pipecolate and NAD+, pH 6.5, 30C
0.0044
purified recombinant His-tagged enzyme, substrates L-pipecolate and NADP+, pH 6.5, 30C
0.0045
purified recombinant His-tagged enzyme, substrates L-proline and NAD+, pH 6.5, 30C
0.33
-
reduction of DELTA1-pyrroline-2-carboxylate, cosubstrate NADPH, pH 8.0, 30C
0.63
purified recombinant His-tagged enzyme, substrates L-proline and NADP+, pH 6.5, 30C
0.67
-
reduction of DELTA1-piperidine-2-carboxylate, cosubstrate NADH, pH 8.0, 30C
1.4
-
oxidation of L-pipecolate, cosubstrate NADP+, pH 8.0, 30C
5.4
-
oxidation of L-proline, cosubstrate NADP+, pH 8.0, 30C
12
purified recombinant His-tagged enzyme, substrates 1-pyrroline-(4R)-hydroxy-2-carboxylate and NADH, pH 6.5, 30C
51
-
reduction of DELTA1-pyrroline-2-carboxylate, cosubstrate NADPH, pH 8.0, 30C
92
-
reduction of DELTA1-piperidine-2-carboxylate, cosubstrate NADPH, pH 8.0, 30C
177
purified recombinant His-tagged enzyme, substrates 1-piperideine-2-carboxylate and NADH, pH 6.5, 30C
220
purified recombinant His-tagged enzyme, substrates 1-piperideine-2-carboxylate and NADPH, pH 6.5, 30C
584
purified recombinant His-tagged enzyme, substrates 1-pyrroline-2-carboxylate and NADPH, pH 6.5, 30C
600
purified recombinant His-tagged enzyme, substrates 1-pyrroline-2-carboxylate and NADH, pH 6.5, 30C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.2
-
DELTA1-pyrroline-2-carboxylate
5.4
-
DELTA1-piperidine-2-carboxylate
6
-
DELTA1-piperidine-2-carboxylate
6.5
reduction reaction
6.8
-
DELTA1-pyrroline-2-carboxylate
10.5
oxidation reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
the organsim can grow on trans-3-hydroxy-L-proline and trans-4-hydroxy-L-proline as sole carbom sources, but also on D-proline and D-lysine
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
62000
recombinant enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
crystallization data
homodimer
2 * 33313, sequence calculation, 2 * 37000, recombinant enzyme, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
unliganded enzyme, in complex with NADPH, and in complex with NADPH and pyrrole-2-carboxylate
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme from kidney
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native enzyme partially
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native enzyme partially from kidney
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene lhpI, 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
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
trans-3-hydroxy-L-proline dehydratase and NAD(P)H-dependent DELTA1-pyrroline-2-carboxylate reductase activity is induced by trans-3-hydroxy-L-proline, D-proline, and D-lysine, but not by trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information