Glutamic acid
Amino acid and neurotransmitter
Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons.
Its molecular formula is C
5H
9NO
4. Glutamic acid exists in two optically isomeric forms; the dextrorotary L-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation. Its molecular structure could be idealized as HOOC−CH(NH
2)−(CH
2)2−COOH, with two carboxyl groups −COOH and one amino group −NH
2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+
3)−(CH
2)2−COOH. It is encoded by the codons GAA or GAG.
The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+
3)−(CH
2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation. This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as monosodium glutamate (MSG). In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH
2)−(CH
2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl.
The one-letter symbol E for glutamate was assigned as the letter following D for aspartate, as glutamate is larger by one methylene –CH2– group.
Chemistry
Ionization
When glutamic acid is dissolved in water, the amino group (−NH
2) may gain a proton (H+
), and/or the carboxyl groups may lose protons, depending on the acidity of the medium.
In sufficiently acidic environments, both carboxyl groups are protonated and the molecule becomes a cation with a single positive charge, HOOC−CH(NH+
3)−(CH
2)2−COOH.
At pH values between about 2.5 and 4.1, the carboxylic acid closer to the amine generally loses a proton, and the acid becomes the neutral zwitterion −OOC−CH(NH+
3)−(CH
2)2−COOH. This is also the form of the compound in the crystalline solid state. The change in protonation state is gradual; the two forms are in equal concentrations at pH 2.10.
At even higher pH, the other carboxylic acid group loses its proton and the acid exists almost entirely as the glutamate anion −OOC−CH(NH+
3)−(CH
2)2−COO−, with a single negative charge overall. The change in protonation state occurs at pH 4.07. This form with both carboxylates lacking protons is dominant in the physiological pH range (7.35–7.45).
At even higher pH, the amino group loses the extra proton, and the prevalent species is the doubly-negative anion −OOC−CH(NH
2)−(CH
2)2−COO−. The change in protonation state occurs at pH 9.47.
Optical isomerism
Glutamic acid is chiral; two mirror-image enantiomers exist: d(−), and l(+). The l form is more widely occurring in nature, but the d form occurs in some special contexts, such as the bacterial capsule and cell walls of the bacteria (which produce it from the l form with the enzyme glutamate racemase) and the liver of mammals.
History
Although they occur naturally in many foods, the flavor contributions made by glutamic acid and other amino acids were only scientifically identified early in the 20th century. The substance was discovered and identified in the year 1866 by the German chemist Karl Heinrich Ritthausen, who treated wheat gluten (for which it was named) with sulfuric acid. In 1908, Japanese researcher Kikunae Ikeda of the Tokyo Imperial University identified brown crystals left behind after the evaporation of a large amount of kombu broth as glutamic acid. These crystals, when tasted, reproduced the novel flavor he detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate.
Synthesis
Biosynthesis
Glutamate is primarily synthesized from α-ketoglutarate, an intermediate of the TCA cycle, through either transamination or reductive amination.
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