1113-59-3 Usage
Description
Bromopyruvic acid, also known as 3-bromopyruvic acid, is a synthetic brominated derivative of pyruvic acid. It is an off-white solid and acts as an affinity label for cysteine residues, as well as a cross-linker between nucleic acids and proteins. Bromopyruvic acid is a highly reactive alkylating agent and has been identified as a potential anti-cancer agent.
Uses
1. Used in Anticancer Applications:
Bromopyruvic acid is used as an anticancer agent for aggressive liver tumors and lung tumors. It has shown potential in eliminating aggressive liver tumors and is involved in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids, which may have therapeutic applications.
2. Used in Affinity Labeling:
Bromopyruvic acid is used as an affinity label for cysteine residues, which can be useful in the study of protein structure and function.
3. Used in Synthesis:
Bromopyruvic acid plays a vital role in the synthesis of various compounds, such as imidazo[1,2-a]pyridine-2-carboxylic acids and substituted pyranones.
4. Used in Drug Delivery Systems:
Bromopyruvic acid is involved in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells.
5. Used in the Fungicide Industry:
3-Bromopyruvic acid is an intermediate in the production of the fungicide thiabendazole, which is used to protect crops from fungal infections.
Preparation
Synthesis method of 3-bromopyruvic acid: add a little concentrated sulfuric acid and solvent dichloromethane to pyruvic acid in a reaction flask, add bromine dropwise for about 3.5h and stir, a white precipitate is produced, then continue to stir for 1h, dilute with cyclohexane and petroleum ether, then cool the reaction mixture to get crystals, filter, wash with petroleum ether and dry to get the finished product of 3-bromopyruvic acid.
Purification Methods
Dry it by azeotropic distillation (with toluene), and then recrystallise it from dry CHCl3. Dry for 48hours at 20o (0.5 torr) over P2O5. Store it at 0o. [Labandiniere et al. J Org Chem 52 157 1987, Beilstein 3 III 1167.]
Check Digit Verification of cas no
The CAS Registry Mumber 1113-59-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1113-59:
(6*1)+(5*1)+(4*1)+(3*3)+(2*5)+(1*9)=43
43 % 10 = 3
So 1113-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
1113-59-3Relevant articles and documents
Synthesis of Phosphoenolpyruvate and Its Use in Adenosine Triphosphate Cofactor Regeneration
Hirschbein, Bernard L.,Mazenod, Francois P.,Whitesides, George M.
, p. 3765 - 3766 (1982)
-
Metal-mediated inhibition of escherichia coli methionine aminopeptidase: Structure-activity relationships and development of a novel scoring function for metal-ligand interactions
Schiffmann, Rolf,Neugebauer, Alexander,Klein, Christian D.
, p. 511 - 522 (2007/10/03)
We report the discovery of thiabendazole as a potent inhibitor (K 1 = 0.4 μM) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range, Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional CoII ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion, We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds, Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.
Kinetic study of the Ce(III)-, Mn(II)-, or ferroin-catalyzed Belousov-Zhabotinsky reaction with pyruvic acid
Lin, Hsing-Lien,Yu, Yueh-O,Jwo, Jing-Jer
, p. 408 - 418 (2007/10/03)
Ce(III)-, Mn(II)-, or ferroin (Fe(phen)32+)-catalyzed reaction of bromate ion and pyruvic acid (PA) or its dimer exhibits oscillatory behavior. Both the open-chain dimer (parapyruvic acid, γ-methyl-γ-hydroxyl-α-keto-glutaric acid, DP