Isocitric acid

• Isocitric
• 3-carboxy -2-hydroxy -pentane- 1 ,5 -dioic acid
• 1- hydroxypropane- 1 ,2,3 -tricarboxylic

Colorless crystalline powder

Fixed

Well in water

Sodium salt

Template: Infobox chemical / molecular formula search available

Isocitric acid is a colorless, water-soluble solid. It is a constitutional isomer of citric acid. The salts are the Isocitrate. L -threo- isocitrate is a metabolic intermediate in the citric acid cycle.

Properties

Isocitric acid is counted due to their three carboxy groups (-COOH) to the organic tricarboxylic acids (see carboxylic acid). Moreover, at position 2 of the carbon, the degree of back hydroxy group (-OH) from a hydroxycarboxylic acid. The molecule is double- chiral, i.e., there are four distinct stereoisomers. The naturally occurring L-threo- isocitric acid can be also referred to as (1S, 2R)- isocitric acid.

Occurrence

Isocitric acid or salts thereof, Isocitrate, are an intermediate product in carbohydrate metabolism of all oxygen consuming animals, including humans. The metabolic sequence ( see Biochemistry ) is called the citric acid cycle.

It occurs in apples, pears, raspberries, blackberries and currants.

Production

A large-scale production has not yet been established, neither the racemate, nor a particular stereoisomer. Using the yeast Yarrowia lipolytica, however, succeeded in refined sunflower oil ( 1S, ​​2R) - isocitrate to produce in large quantities and in a favorable ratio of isocitrate to citrate. The two components are obtained after filtering off the biomass by a electrodialysis and separated by an esterification, wherein the citric acid is crystallized and Isocitronensäureester remains liquid.

Physiology

(1S, 2R)- isocitrate is an intermediate product of several metabolic pathways in all living things. It is produced by using the aconitase in a low concentration of citrate ( cis - aconitate as an intermediate product) in the context of the citric acid cycle.

Isocitrate is further processed

• Of the isocitrate dehydrogenase to alpha -ketoglutarate in the citric acid cycle
• Using the isocitrate lyase to glyoxylate and succinate, as part of the glyoxylate cycle of bacteria, or in the glyoxysomes of plants, fungi, algae and protozoa.
• To 2 - Caffeoylisocitrat catalyzed by a specific enzyme (EC 2.3.1.126 ) in Amaranthus species