Ligand D-alanine

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Basic Ligand Information

Molecular Structure
Picture of D-alanine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H7NO2
D-alanine
QNAYBMKLOCPYGJ-UWTATZPHSA-N
Synonyms:
D-2-aminopropionic acid, D-Ala, D-alpha-alanine, R-alanine


Show all pahtways known for Show all BRENDA pathways known for D-alanine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-alanine + H2O + O2 = pyruvate + NH3 + H2O2
show the reaction diagram
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D-alanine + H2O + FAD = pyruvate + NH3 + FADH2
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D-alanine + 2-oxoglutarate = pyruvate + D-glutamate
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D-alanine + pyridoxal 5'-phosphate = pyridoxamine 5'-phosphate + pyruvate
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D-alanine = L-alanine
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D-alanine + (R)-lactate + ATP = D-alanyl-(R)-lactate + ADP + phosphate
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ATP + D-Ala + membrane-acceptor = ?
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D-alanine + D-serine + ATP = D-alanyl-D-serine + ADP + phosphate
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In Vivo Product in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[(4-D-Ala)-(2-GlcNAc)-Rib-ol-P]n-[Gro-P]m-ManNAc-GlcNAc-PP-peptidoglycan + H2O = [(2-GlcNAc)-Rib-ol-P]n-[Gro-P]m-ManNAc-GlcNAc-PP-peptidoglycan + D-alanine
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D-Ala-D-Ala + H2O = D-Ala + D-Ala
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L-Ala-gamma-D-Glu-meso-diaminopimelyl-D-Ala + H2O = L-Ala-gamma-D-Glu-meso-diaminopimelyl + D-Ala
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UDP-MurNAc-pentapeptide + H2O = UDP-MurNAc-tetrapeptide + D-Ala
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L-alanine = D-alanine
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Substrate in Enzyme-catalyzed Reactions (220 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-alanine + L-ascorbate + O2 = ?
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D-Ala + H2O + NAD+ = pyruvate + NH3 + NADH
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D-alanine + H2O + 2 ferricytochrome = pyruvate + NH3 + 2 ferrocytochrome + 2 H+
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D-alanine + H2O + O2 = ?
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D-alanine + oxidized 2,6-dichloroindophenol + H2O = pyruvate + NH3 + reduced 2,6-dichloroindophenol
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choloyl-CoA + D-alpha-alanine = CoA + D-alpha-alanylcholate
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2-phosphonoacetaldehyde + D-alanine = (2-aminoethyl)phosphonate + pyruvate
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D-alanine + 4,5-dioxopentanoate = 5-aminolevulinate + pyruvate
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D-Ala + pyruvate = L-Ala + ? + CO2
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D-alanine + pyridoxal 5'-phosphate = pyridoxamine 5'-phosphate + pyruvate
show the reaction diagram
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D-alanine = L-alanine
show the reaction diagram
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D-Ala = L-Ala
show the reaction diagram
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D-alanine = L-alanine
show the reaction diagram
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D-Ala = L-Ala
show the reaction diagram
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D-alanine = L-alanine
show the reaction diagram
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ATP + gamma-L-Glu-L-Cys + D-Ala = ADP + phosphate + gamma-Glu-L-Cys-D-Ala
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Product in Enzyme-catalyzed Reactions (302 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
pyruvate + NH3 + NADPH + H+ = D-alanine + NADP+
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5'-phospho-pyridoxyl-D-alanine + H2O + O2 = pyridoxal 5'-phosphate + D-alanine + H2O2
show the reaction diagram
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N-methyl D-alanine + 2,6-dichlorophenolindophenol + H2O = D-alanine + formaldehyde + reduced 2,6-dichlorophenolindophenol
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alpha-methylserine + tetrahydrofolate = D-alanine + 5,10-methylenetetrahydrofolate
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GlcNAc-MurNGlyc-L-Ala1-D-iGln2-meso-DapNH23-D-Ala4 + D-methionine = GlcNAc-MurNGlyc-L-Ala1-D-iGln2-meso-DapNH23-D-Met4 + D-alanine
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D-alanine methyl ester + H2O = D-alanine + methanol
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Pro-D-Ala + H2O = Pro + D-Ala
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pyroglutamyl-D-Ala + H2O = pyroglutamate + D-Ala
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benzyloxycarbonyl-Gly-Pro-D-Ala + H2O = benzyloxycarbonyl-Gly-Pro + D-Ala
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N-carbamoyl-D-Ala + H2O = D-Ala + NH3 + CO2
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DL-alpha-aminopropionitrile + H2O = D-alanine + NH3
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alpha-methyl-beta-phenylserine = D-alanine + benzaldehyde
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L-Ala = D-Ala
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L-alanine = D-alanine
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L-alanine = D-alanine
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation of isoforms prolidase I and prolidase II
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1 mM, relative activity 120%
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106% activity at 50 mM with D-methionine as substrate
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Inhibitor in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive to 1-aminocyclopropane-1-carboxylate
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45% inhibition in the presence of 1 mM D-alanine
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oxidation of 3,4-dehydro-DL-proline by membrane fractions from strain UMM5 is competitively inhibited by D-alanine
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competitive vs. L-alanine
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competitive inhibitor with L-alanine as varied substrate and glyoxylate as fixed substrate. Uncompetitive inhibitor with glyoxylate as varied substrate and L-alanine as fixed substrate; competitive with L-alanine, uncompetitive with glyoxylate
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allosteric inhibition
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94% residual activity at 1 mM
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competitive inhibition, 10 mM
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competitive
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substrate inhibition
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94% residual activity at 5 mM with L-methionine as substrate
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3D Structure of Enzyme-Ligand-Complex (PDB) (112 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (190 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.62
-
pH and temperature not specified in the publication
15.5
-
-
0.74
-
pH 8.7, 37°C
0.0036
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pH 7.7, 25°C, recombinant enzyme, with pimeloyl-CoA
0.04
-
pH 8.5, 25°C, synthesis of (2-aminoethyl)phosphonate
0.2
-
with pyruvate as cosubstrate, decarboxylation
1830
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pH 10.0, 35°C, recombinant His-tagged enzyme

KM Value (297 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
742
-
pH and temperature not specified in the publication
0.46
-
pH 8.7, 37°C
0.054
-
30°C, recombinant enzyme
0.2015
-
pH 7.7, 25°C, recombinant enzyme, with pimeloyl-CoA
2.9
-
-
3.4
-
-
0.018
-
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Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
28
-
pH7.0, 30°C
40
55
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References & Links