Fumarate

Fumarate is an important organic compound in biochemistry, playing a pivotal role in the Krebs cycle (also known as the citric acid cycle or TCA cycle), which is a crucial part of cellular respiration. It is the anion form of fumaric acid and has the chemical formula C4H2O4^2−.

Structure and Properties

Fumarate is a derivative of fumaric acid, which is a dicarboxylic acid. Structurally, it consists of a butene backbone with two carboxylate groups (COO−) attached at each end. This configuration makes fumarate a trans compound, distinguishing it from its cis isomer, maleate. The trans configuration of fumarate is more stable due to less steric hindrance between the hydrogen atoms attached to the carbon-carbon double bond.

Biological Role

In metabolism, fumarate is a key intermediate in the Krebs cycle. It is formed by the oxidation of succinate through the enzyme succinate dehydrogenase. Fumarate is then converted to malate by the enzyme fumarase (or fumarate hydratase), through the addition of a water molecule.

Fumarate also plays a role in the urea cycle and in the generation of amino acids, serving as a source of nitrogen in the form of ammonia. Additionally, it acts as a precursor in the synthesis of various biomolecules.

Medical Significance

Fumarate is used in medicine primarily in its ester forms, such as dimethyl fumarate, for the treatment of conditions like multiple sclerosis. It has been shown to have anti-inflammatory and neuroprotective effects. Research continues into its mechanisms and potential applications in other diseases.

Industrial Uses

In industry, fumarate is used in the production of polyester resins and plastics. It is also a component in some food additives, where it serves as an acidity regulator and can be found in the ingredients list of some processed foods.

See Also

• Citric acid cycle
• Metabolic pathway
• Cellular respiration