This article appears to contradict another article: Monosodium glutamate. Please see discussion on the talk page.

Glutamic acid
Systematic name	(2S)-2-aminopentanedioic acid
Chemical formula	C5H9NO4
Molar mass	147.13 g mol−1
Complete data

Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Image File history File links Circle-contradict. ... Chemical structure of monosodium glutamate Monosodium glutamate, sodium glutamate, flavour enhancer 621 EU food additive code: E621. ... Image File history File links Height_setter. ... Image File history File links Download high resolution version (1587x1394, 28 KB) Licensing File links The following pages link to this file: Amino acid Glutamic acid ... Image File history File links Download high resolution version (739x724, 24 KB) Licensing File links The following pages link to this file: Glutamic acid ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... Physical properties Hazard properties Flash point - N/A R/S statement R: N/A S: N/A RTECS number: N/A Chemical properties Pharmacological properties OrganicBox_complete References a  CID 23327 from PubChem (D-glutamic acid) a  CID 33032 from PubChem (L-glutamic acid) This article is maintained by WP:Chemicals... An anion is an ion with negative charge. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... The general structure of an amino acid molecule, with the amine group on the left and the carboxyl group on the right. ... This article or section may be confusing or unclear for some readers, and should be edited to rectify this. ...

Structure

As its name indicates, it is acidic, with a carboxylic acid component to its side chain. Generally either the amino group will be protonated or one or both of the carboxylic groups will be deprotonated. At neutral pH all three groups are ionized and the species has a charge of -1. The pKa value for Glutamic acid is 4.1. This means that at pH below this value it will be protonated (COOH) and at pH above this value it will be deprotonated (COO-) For other uses, see Acid (disambiguation). ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ... Protonation is the addition of a proton (H+) to an atom, molecule, or ion. ... In chemistry, a carboxyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl (-OH) group, typically written as -COOH: where R is a hydrogen or an organic group. ... Deprotonation is a chemistry term that refers to the removal of a proton (hydrogen ion H+) from a molecule, forming the conjugate base. ... pH is a measure of the acidity of a solution in terms of activity of hydrogen (H+). For dilute solutions, however, it is convenient to substitute the activity of the hydrogen ions with the molarity (mol/L) of the hydrogen ions (however, this is not necessarily accurate at higher concentrations...

A three-letter designation for either Gln or Glu is Glx—this is often used in cases in which peptide sequencing reactions may convert glutamine to glutamate (or vice versa), leaving the original identity of the amino acid in doubt. The one-letter abbreviation is E for glutamic acid and Q for glutamine. Glutamine is one of the 20 amino acids encoded by the standard genetic code. ...

Synthesis

Natural

Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... Synthesis NAcGlu is synthesized from Glu and Ac-CoA by NAGS and hydrolyzed by a specific hydrolase. ... Ketoglutaric acid is used for either of two crystalline keto derivatives C5H6O5 of glutaric acid. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ... Ketoglutaric acid is used for either of two crystalline keto derivatives C5H6O5 of glutaric acid. ... The general structure of an amino acid molecule, with the amine group on the left and the carboxyl group on the right. ... In biochemistry, a transaminase or an aminotransferase is an enzyme that catalyzes a type of reaction between an amino acid and an α-keto acid. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD+) and nicotinamide adenine dinucleotide phosphate (NADP) are two important cofactors found in cells. ... Folic acid and folate (the anion form) are forms of a water-soluble B vitamin. ... Folic acid and folate (the anion form) are forms of a water-soluble B vitamin. ...

Function

In metabolism

Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. A key process in amino acid degradation is transamination, in which the amino group of an amino acid is transferred to an α-ketoacid, typically catalysed by a transaminase. The reaction can be generalised as such: Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... In chemistry, an amino acid is any molecule that contains both amino and carboxylic acid functional groups. ... Transamination is the reaction between an amino acid and an alpha-keto acid. ... In biochemistry, a transaminase or an aminotransferase is an enzyme that catalyzes a type of reaction between an amino acid and an α-keto acid. ...

R₁-amino acid + R₂-α-ketoacid ⇌ R₁-α-ketoacid + R₂-amino acid

A very common α-ketoacid is α-ketoglutarate, an intermediate in the citric acid cycle. When α-ketoglutarate undergoes transamination, it always results in glutamate being formed as the corresponding amino acid product. The resulting α-ketoacid product is often a useful one as well, which can contribute as fuel or as a substrate for further metabolism processes. Examples are as follows: Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle) is a series of chemical reactions of central importance in all living cells that utilize oxygen as part of cellular respiration. ...

alanine + α-ketoglutarate ⇌ pyruvate + glutamate

aspartate + α-ketoglutarate ⇌ oxaloacetate + glutamate

Both pyruvate and oxaloacetate are key components of cellular metabolism, contributing as substrates or intermediates in fundamental processes such as glycolysis, gluconeogenesis and also the citric acid cycle. Alanine (Ala, A) also 2-aminopropanoic acid is a non-essential α-amino acid. ... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... Aspartic acid, also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. ... Glycolysis is a biochemical pathway by which a molecule of glucose (Glc) is oxidized to two molecules of pyruvic acid (Pyr). ... Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle) is a series of chemical reactions of central importance in all living cells that utilize oxygen as part of cellular respiration. ...

Glutamate also plays an important role in the body's disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase, as follows: General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... Deamination is the removal of an amine group from a molecule. ... Glutamate dehydrogenase is an enzyme, present in mitochondria, as are some of the other enzymes required for urea synthesis, that converts glutamate to α-Ketoglutarate, and vice versa. ...

glutamate + water + NAD⁺ → α-ketoglutarate + NADH + ammonia + H⁺

Ammonia (as ammonium) is then excreted predominantly as urea, synthesised in the liver. Transamination can thus be linked to deamination, effectively allowing nitrogen from the amine groups of amino acids to be removed, via glutamate as an intermediate, and finally excreted from the body in the form of urea. Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD+) and nicotinamide adenine dinucleotide phosphate (NADP) are two important cofactors found in cells. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD+) and nicotinamide adenine dinucleotide phosphate (NADP) are two important cofactors found in cells. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ... Fumes from hydrochloric acid and ammonia forming a white cloud of ammonium chloride Ammonium is also an old name for the Siwa oasis in western Egypt. ... Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Non-proprietary Names (rINN) in use in Europe. ... The liver is the largest internal organ of the human body. ...

As a neurotransmitter

Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Chemical structure of D-Aspartic Acid, a common Amino Acid neurotransmitter. ... The nervous system of an animal coordinates the activity of the muscles, monitors the organs, constructs and also stops input from the senses, and initiates actions. ... Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ... A. Schematic of an electrophysiological recording of an action potential showing the various phases which occur as the wave passes a point on a cell membrane. ... Glutamate is a neurotransmitter in nerve cells which binds to all glutamate receptors located on neuron membranes, and is an example of a transmembrane receptor. ... The NMDA receptor (NMDAR) is an ionotropic receptor for glutamate (NMDA (N-methyl d-aspartate) is a name of its selective specific agonist). ... In neuroscience, synaptic plasticity is the ability of the connection, or synapse, between two neurons to change in strength. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... In psychology, memory is the ability of an organism to store, retain, and subsequently recall information. ...

Glutamate transporters^[3] are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: Glutamate transporters exist in the membranes of neurons and glial cells to remove excess amounts of the amino acid neurotransmitters glutamate and aspartate from the synapse. ... Drawing by Santiago Ramón y Cajal of neurons in the pigeon cerebellum. ... Neuroglia cells of the brain shown by Golgis method. ... In cell biology, molecular biology and related fields, the word extracellular means outside the cell. It is used in contrast to intracellular (inside the cell). ... The NMDA receptor (NMDAR) is an ionotropic receptor for glutamate (NMDA (N-methyl d-aspartate) is a name of its selective specific agonist). ... Excitotoxicity is the pathological process by which neurons are damaged and killed by the overactivation of excitatory neurotransmitter receptors such as the NMDA receptor and AMPA receptor (which belong to the glutamate receptor family). ... A cell undergoing apoptosis. ...

• Damage to mitochondria from excessively high intracellular Ca^2+[4].
• Glu/Ca²⁺-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes.

Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... General Name, Symbol, Number calcium, Ca, 20 Chemical series alkaline earth metals Group, Period, Block 2, 4, s Appearance silvery white Atomic mass 40. ... In molecular biology, a transcription factor is a protein that binds DNA at a specific promoter or enhancer region or site, where it regulates transcription. ... The ischemic cascade is a series of biochemical reactions that take place in the brain after seconds to minutes of ischemia (inadequate blood supply) (Arnold, 2003). ... For other articles with similar names, see Stroke (disambiguation). ... Amyotrophic lateral sclerosis (ALS, sometimes called Lou Gehrig’s disease, Maladie de Charcot or motor neurone disease) is a chronic, progressive, invariably fatal neurological disease. ... Thanks to the Grasspea Flour, an aquatint print by Goya showing the effects of Lathyrism Lathyrism or Neurolathyrism is a neurological disease of humans and domestic animals, caused by eating certain legumes of the genus Lathyrus. ...

Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarisations around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarising shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ... In neuroscience, depolarization refers to the event a neuron undergoes when its membrane potential grows more positive with respect to the extracellular solution. ... Look up second in Wiktionary, the free dictionary. ... ...

Experimental techniques to detect glutamate in intact cells include using a genetically-engineered nanosensor^[2]. The sensor is a fusion of a glutamate-binding protein and two fluorescent proteins. When glutamate binds, the fluorescence of the sensor under ultraviolet light changes by resonance between the two fluorophores. Introduction of the nanosensor into cells enables optical detection of the glutamate concentration. Synthetic analogs of glutamic acid that can be activated by ultraviolet light have also been described^[6]. This method of rapidly uncaging by photostimulation is useful for mapping the connections between neurons, and understanding synapse function. Nanosensors are a technology that may exist in the future. ... Ultraviolet (UV) light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than soft X-rays. ... Fluorescence resonance energy transfer (or Förster resonance energy transfer) describes an energy transfer mechanism between two fluorescent molecules. ... Ultraviolet (UV) light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than soft X-rays. ... Photostimulation is the use of light to artificially activate biological compounds, cells, or even whole organisms. ...

GABA precursor

Glu also serves as the precursor for the synthesis of the inhibitory GABA in GABA-ergic neurons. A precursor is something that existed before and was incorporated into something that came later. ... Gaba may refer to: Gabâ or gabaa (Philippines), the concept of negative karma of the Cebuano people GABA, the gamma-amino-butyric acid neurotransmitter GABA receptor, in biology, receptors with GABA as their endogenous ligand Gaba 1 to 1, an English conversational school in Japan Marianne Gaba, a US model...

Sources and absorption

Glutamic acid is present in a wide variety of foods and is responsible for one of the five basic tastes of the human sense of taste (umami), especially in its physiological form, the sodium salt of glutamate in a neutral pH. Ninety-five percent of the dietary glutamate is metabolized by intestinal cells in a first pass ^[5]. The basic tastes are the commonly recognized types of taste sensed by humans. ... Taste is one of the most common and fundamental of the senses of animals. ... Human taste sensory organs, called taste buds or gustatory calyculi, and concentrated on the upper surface of the tongue, appear to be receptive to relatively few chemical species as tastes. ...

Overall, glutamic acid is the single largest contributor to intestinal energy. As a source for umami, the sodium salt of glutamic acid, monosodium glutamate (MSG) is used as a food additive to enhance the flavor of foods, although an identical effect can be achieved by mixing and cooking together different ingredients rich in this amino acid and other umami substances as well. General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... A magnified crystal of a salt (halite/sodium chloride) A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral (without a net charge). ... Chemical structure of monosodium glutamate Monosodium glutamate, sodium glutamate, flavour enhancer 621 EU food additive code: E621. ... Food additives are substances added to food to preserve flavour or improve its taste and appearance. ...

Another source of MSG is fruits, vegetables and nuts that have been sprayed with Auxigro. Auxigro is a growth enhancer that contains 30% glutamic acid. Auxigro is a chemical-based growth-enhancer that is currently approved by the EPA for spray on fruits, vegetables, and grains. ...

Pharmacology

The drug phencyclidine (more commonly known as PCP) antagonizes glutamic acid non-competitively at the NMDA receptor. For the same reasons, sub-anaesthetic doses of Ketamine have strong dissociative and hallucinogenic effects. Glutamate does not easily pass the blood brain barrier, but: "glutamate flux from plasma into brain is mediated by a high affinity transport system at the BBB" [1]. It can also be converted into glutamine. Phencyclidine (a contraction of the chemical name phenylcyclohexylpiperidine), abbreviated PCP, is a dissociative drug formerly used as an anesthetic agent, exhibiting hallucinogenic and neurotoxic effects. ... Antagonists In medicine and biology, a receptor antagonist is a ligand that inhibits the function of an agonist and inverse agonist for a specific receptor. ... For the collaborative acoustic project, see Katamine. ...

Glutamate transport and supply are obvious targets for the treatment of epilepsy, therefore. In particular Glutamate Restriction Diets are now claiming success anecdotally, by limiting or eliminating intake of wheat, peanut, soy and bean. No similar diets for schizophrenia are known.

References

1. Nelson DL and Cox MM. Lehninger Principles of Biochemistry, 4th edition.
2. ^a  Okumoto, S., et al. (2005). "Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors". Proceedings of the National Academy of Sciences U.S.A 102 (24): 8740-8745. PMID 15939876. Free text
3. ^a  Molecular pharmacology of glutamate transporters, EAATs and VGLUTs. Brain Res Brain Res Rev. 2004 Jul; 45(3):250-65. PubMed
4. ^a  Delayed increase of Ca2+ influx elicited by glutamate: role in neuronal death. Mol Pharmacol. 1989 Jul;36(1):106-12; PubMed
5. ^a  Reeds, P.J., et al. (2000). "Intestinal glutamate metabolism". Journal of Nutrition 130 (4s): 978S-982S. PMID 10736365.. Free text
6.   Corrie, J.E., et al. (1993). "Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate". Journal of Physiology 465 (Jun): 1-8. PMID 7901400. Free text

Image File history File links Free_text. ... Image File history File links Free_text. ...

External links

• Link page to external chemical sources.