16490
Bromopyruvic acid
≥98.0%
Synonym(s):
3-Bromo-2-oxopropionic acid
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About This Item
Linear Formula:
BrCH2COCOOH
CAS Number:
Molecular Weight:
166.96
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-206-5
Beilstein/REAXYS Number:
1746786
MDL number:
Assay:
≥98.0%
Form:
(Powder or Crystals or Flakes)
Quality Level
assay
≥98.0%
form
(Powder or Crystals or Flakes)
mp
77-82 °C
solubility
water: soluble 1 g/10 mL, clear to very slightly hazy, colorless
functional group
bromo, carboxylic acid, ketone
storage temp.
2-8°C
SMILES string
OC(=O)C(=O)CBr
InChI
1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
InChI key
PRRZDZJYSJLDBS-UHFFFAOYSA-N
General description
Bromopyruvic acid is an affinity label for cysteine residues†. It acts as cross-linker between nucleic acids and proteins. Kinetics of inactivation of pancreatic ribonuclease A by bromopyruvic acid has been investigated.
may contain traces of dibromopyruvic acid
Application
Bromopyruvic acid was used in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids.
Other Notes
Affinity label for cysteine residues; Cross-linker between nucleic acids and proteins
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Articles
Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.
I Kameshita et al.
Journal of biochemistry, 86(5), 1251-1257 (1979-11-01)
Phosphoenolpyruvate carboxylase [EC 4.1.1.31] from Escherichia coli W was alkylated by incubation with bromopyruvate, substrate analog, leading to irreversible inactivation. The reaction followed pseudo-first-order kinetics. Mg2+, an essential cofactor for catalysis, enhanced the inactivation, and the enhancing effect increased as
Ananda Herath et al.
Organic letters, 12(3), 412-415 (2009-12-30)
The first continuous flow synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids directly from 2-aminopyridines and bromopyruvic acid has been developed, representing a significant advance over the corresponding in-flask method. The process was applied to the multistep synthesis of imidazo[1,2-a]pyridine-2-carboxamides, including a Mur ligase
M H Wang et al.
The Biochemical journal, 320 ( Pt 1), 187-192 (1996-11-15)
The kinetic theory of substrate reaction during the modification of enzyme activity [Duggleby (1986) J. Theor. Biol. 123, 67-80; Wang and Tsou (1990) J. Theor. Biol. 142, 531-549] has been applied to a study of the inactivation kinetics of ribonuclease