Ligand Bromopyruvate

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Basic Ligand Information

Molecular Structure
Picture of Bromopyruvate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H3BrO3
Bromopyruvate
DCQWRDUXRZSWHI-UHFFFAOYSA-N
Synonyms:
2-bromopyruvate, 2-Keto-(3S)-3-bromopyruvate, 3-bromo-2-oxopropionic acid, 3-Bromopyruvate

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
bromopyruvate + NADH = 3-bromo-2-hydroxypropanoate + NAD+
show the reaction diagram
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bromopyruvate + NADH = 3-bromo-2-hydroxypropanoate + NAD+
show the reaction diagram
-
3-bromopyruvate + NADH = 3-bromo-2-hydroxypropanoate + NAD+
show the reaction diagram
-
2-hydroxybutanoate + bromopyruvate + ? = bromolactate + pyruvate + ?
show the reaction diagram
-
3-bromopyruvate + NH3 + NADH = 2-amino-3-bromopropanoate + NAD+ + H2O
show the reaction diagram
-
L-glutamine + 3-bromopyruvate = 2-oxoglutaramate + 2-amino-3-bromopropionic acid
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (48 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
irreversible inactivation
-
suicide substrate
-
phosphoenolpyruvate, but not arabinose-5-phosphate protects
-
irreversible, inhibitory effect is increased by UDP-GlcNAc
-
10 mM, 28% inhibition
-
0.1 mM, 15 min, 2% residual activity in absence of substrate S-pantetheine-3-pyruvate, 76% residual activity in presence of the substrate S-pantetheine-3-pyruvate
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3(R,S)-[3-3H2]bromopyruvate is asymetrically detritiated by the enzyme yielding 3(S)-[3-3H,H]bromopyruvate concomitant with inactivation
-
Ki: 0.018 mM
-
inactivation prevented by chorismate and Trp
-
complete inactivation at equimolar concentrations
-
85% inhibition at 1 mM, pyruvate or 2-keto-4-hydroxyglutarate protect; substrate analog. Treatment results in a time- and concentration-dependent loss of enzymatic activity. The substrates pyruvate and 2-keto-4-hydroxyglutarate provide more than 90% protection against inactivation by bromopyruvate, no protective effect is seen with glycolaldehyde. 1.1 mol of bromopyruvate is incorporated per enzyme subunit by esterification of residue Glu45
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a active-site-directed irreversible inhibitor, modification of three active sites per hexamer abolishes essentially all activity of the hexamer, pH dependence of inactivation
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
269
-
-
0.36
-
transhydrogenation reaction

KM Value (2 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
10
-
-
4.4
-
transhydrogenation reaction

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.028
-
assay with whole enzyme complex
6.47
-
pH 7.5, 37°C
0.06
-
pH 7.5, 25°C
1.99
-
-
0.018
-
-

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for Bromopyruvate

ChEBI
PubChem
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PubChem