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BRENDA support

Ligand L-proline

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Basic Ligand Information

Molecular Structure
Picture of L-proline (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H9NO2
L-proline
ONIBWKKTOPOVIA-BYPYZUCNSA-N
Synonyms:
(2S)-pyrrolidinium-2-carboxylate, L-Pro, L-proline[side 2], Pro, proline
Pathway Source
Pathways
BRENDA
(5R)-carbapenem carboxylate biosynthesis, arginine metabolism, fumitremorgin biosynthesis, ornithine metabolism, proline metabolism
KEGG
ABC transporters, Aminoacyl-tRNA biosynthesis, Arginine and proline metabolism, Biosynthesis of amino acids, Biosynthesis of secondary metabolites more
MetaCyc
(5R)-carbapenem carboxylate biosynthesis, actinomycin D biosynthesis, apratoxin A biosynthesis, aureobasidin A biosynthesis, brominated pyrroles biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for L-proline

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (22 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-proline + 2-oxoglutarate + O2 = cis-3-hydroxy-L-proline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = cis-4-hydroxy-L-proline + succinate + CO2
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L-proline + 2-oxoglutarate + O2 = trans-4-hydroxy-L-proline + succinate + CO2
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L-Pro + H2O + O2 = ?
show the reaction diagram
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L-proline + NAD+ = DELTA1-pyrroline-2-carboxylate + NADH + H+
show the reaction diagram
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thiamine + proline = 4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyrrolidine-2-carboxylic acid
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ATP + H2O + proline/out = ADP + phosphate + proline/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (20 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-pyrroline-2-carboxylate + NADPH + H+ = L-proline + NADP+
show the reaction diagram
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DELTA1-pyrrolidine 2-carboxylate + NADPH + H+ = L-proline + NADP+
show the reaction diagram
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Gly-Pro + H2O = Glycine + proline
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Z-Gly-Pro-Leu-Gly-Pro + H2O = Z-Gly-Pro + L-Leu + Gly + L-Pro
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L-ornithine = L-proline + NH3
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Substrate in Enzyme-catalyzed Reactions (105 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-proline + 2-oxoglutarate + O2 = 4-hydroxyproline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = cis-3-hydroxy-L-proline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = trans-3-hydroxyproline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = cis-4-hydroxy-L-proline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = trans-4-hydroxy-L-proline + succinate + CO2
show the reaction diagram
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L-proline + 2-oxoglutarate + O2 = trans 3-hydroxy-L-proline + succinate
show the reaction diagram
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L-proline + H2O + NAD+ = ? + NH3 + NADH
show the reaction diagram
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L-proline + H2O + NAD+ = ? + NH3 + NADH + H+
show the reaction diagram
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L-Pro + H2O + O2 = 2-oxopentanoic acid + NH3 + H2O2
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L-Pro + H2O + oxidized 2,6-dichlorophenolindophenol = ?
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L-proline + NADP+ = 1-pyrroline-2-carboxylate + NADPH + H+
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L-proline + NAD+ = DELTA1-pyrroline-2-carboxylate + NADH + H+
show the reaction diagram
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L-proline + O2 = ?
show the reaction diagram
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L-proline + O2 = ?
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L-proline + coenzyme Q1 = ?
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thiamine + proline = 4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]pyrrolidine-2-carboxylic acid
show the reaction diagram
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L-proline + 2-oxoglutarate = ?
show the reaction diagram
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L-Pro = ?
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L-proline = D-proline
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ATP + L-proline + tRNAGlu = AMP + diphosphate + L-prolyl-tRNAGlu
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ATP + H2O + Pro/out = ADP + phosphate + Pro/in
show the reaction diagram
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ATP + H2O + proline/out = ADP + phosphate + proline/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (241 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-pyrroline-5-carboxylate + NADH + H+ = L-proline + NAD+
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1-pyrroline-5-carboxylate + NADH + H+ = L-proline + NAD+
show the reaction diagram
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DELTA1-pyrrolidine 2-carboxylate + NADPH + H+ = L-proline + NADP+
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L-Pro benzyl ester + H2O = L-Pro + benzoic acid
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Pro-Trp + H2O = Pro + Trp
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Met-Pro + H2O = Met + Pro
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L-Pro-7-amido-4-methylcoumarin + H2O = L-Pro + 7-amino-4-methylcoumarin
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L-prolyl 4-nitroanilide + H2O = L-proline + 4-nitroaniline
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L-prolyl 4-nitroanilide + H2O = L-proline + 4-nitroaniline
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Lys-Ala-Pro + H2O = Lys-Ala + Pro
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Ala-Ala-Ala-Pro + H2O = Ala-Ala-Ala + Pro
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(2-aminobenzoyl)-FFFP + H2O = (2-aminobenzoyl)-FFF + Pro
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Pro-beta-naphthylamide + H2O = Pro + 2-naphthylamine
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Z-Gly-Pro-Leu-Gly-Pro + H2O = Z-Gly-Pro + L-Leu + Gly + L-Pro
show the reaction diagram
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Z-Gly-Pro-Leu-Gly-Pro + H2O = Z-Gly-Pro + L-Leu + Gly + L-Pro
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angiotensin I + H2O = Asp-Arg-Val-Tyr-Ile-His + Pro + Phe-His-Leu
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Gly-Pro + H2O = Glycine + proline
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L-proline amide + H2O = L-proline + NH3
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Pro-NH2 + H2O = Pro + NH3
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N-alpha-acetyl-L-proline + H2O = acetate + L-proline
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N-acetylproline + H2O = acetate + proline
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prolinamide + H2O = NH3 + proline
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L-proline-beta-naphthylamide + H2O = L-proline + 2-naphthylamine
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L-ornithine = L-proline + NH3
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5-L-glutamyl-L-proline = 5-oxoproline + L-proline
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D-proline = L-proline
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ATP + H2O + Pro/out = ADP + phosphate + Pro/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (8 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 M, 35% activation, at high substrate concentrations
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in the presence of L-proline, high POX activity is sufficient to induce mitochondria-mediated apoptosis
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increased uptake leads to activation
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stimulates, stimulation pattern of MtrA is similar to that of MtrB
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at low temperatures the inhibition switches over into allosteric activation and the biosynthesis of proline is started
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with proline the residual activity of AK after incubation in guanidine hydrochloride is higher than without proline
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0.4 M, 72.2% residual activity after 60°C heat treatment
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Inhibitor in Enzyme-catalyzed Reactions (60 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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30% inhibition at 250 mM, with glycine
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concentrations of 0.1 M have a slight accelerating effect on thermal aggregation of glycogen phosphorylase b. The suppression aggregation at high proline concentrations is mainly due to the protective action of proline on the stage of unfolding of the molecule
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hyperprolinemia type II is an autosomal recessive disorder caused by severe deficiency of enzyme DELTA1-pyrroline-5-carboxylic acid dehydrogenase leading to tissue accumulation of proline. Proline has direct inhibitory effect on aspartate transaminase activity of different brain regions leading to lesser synthesis of glutamate thereby causing neurological dysfunctions
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inhibits enzyme self-association and interaction with glycogen and phosphorylase b
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inhibits the enzyme at 35-50°C and concentrations of 1-3 M
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at micromolar concentrations
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competitive
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10 mM: 30% inhibition
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weak
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competitive inhibition of cysteinylation. A 40fold excess over L-cysteine concentration reduces the cysteinylation activity by over 80%, no inhibition of mutant E103A
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weak, gamma-glutamyl transferase activity
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the uncompetitive nature of the inhibition of the dead-end inhibitor, L-proline, versus ATP is consistent with a mechanism with ordered substrate binding where ATP binds first followed by (2S,5S)-carboxymethylproline
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (122 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.2
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100 mM N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid pH 7.0, 5 mM 2-oxoglutarate, 5 mM L-proline, 5 mM L-ascorbate, 1 mM FeSO4, 35°C
20.8
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pH 9, 30°C
212.8
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3.42
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purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
0.0003
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wild-type, 37°C, pH not specified in the publication

KM Value (173 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.445
-
-
0.54
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pH 7.5, 25°C
0.445
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pH 7.5, 35°C
0.64
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pH 9, 30°C
18.5
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purified recombinant His-tagged enzyme, with NADPH, pH 7.0, 30°C
98
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wild-type, 37°C, pH not specified in the publication
3
3.5
pH 8.0, 30°C, recombinant enzyme
111
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Ki Value (28 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.145
-
pH 7.5, 37°C, recombinant wild-type enzyme, competitive inhibition
5.5
-
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0.198
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pH 7.0, 25°C

IC50 Value (42 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

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Links to other databases for L-proline

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ChEBI
PubChem
ChEBI
PubChem