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Glutamate metabolism

Glutamic acid
Glutamic acid in non ionic form
Sample of L-Glutamic acid.jpg
Names
Systematic IUPAC name
2-Aminopentanedioic acid
Other names
2-Aminoglutaric acid
Identifiers
56-86-0 (L isomer) N
617-65-2 (D/L racemate) N
3D model (Jmol) Interactive image
ChEBI CHEBI:18237 YesY
ChEMBL ChEMBL276389. N
ChemSpider 591 YesY
ECHA InfoCard 100.009.567
E number E620 (flavour enhancer)
KEGG D0434 N
UNII 61LJO5I15S YesY
Properties
C5H9NO4
Molar mass 147.13 g·mol−1
Appearance white crystalline powder
Density 1.4601 (20 °C)
Melting point 199 °C (390 °F; 472 K) decomposes
7.5 g/L (20 °C)
Solubility 0.00035g/100g ethanol
(25 °C)
Acidity (pKa) 2.10, 4.07, 9.47
-78.5·10−6 cm3/mol
Hazards
Safety data sheet See: data page
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Glutamic acid is an α-amino acid with formula C
5
H
9
O
4
N
. It is usually abbreviated as Glu or E in biochemistry. 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 acid water solutions, the molecule assumes an electrically neutral zwitterion structure OOC-CH(NH+
3
)-(CH
2
)2-COOH.

Glutamic acid is used by almost all living beings in the biosynthesis of proteins, being specified in DNA by the codons GAA or GAG. It is non-essential in humans, meaning the body can synthesize it.

The acid can lose one proton from 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 is also responsible for the umami (savory) flavor of certain foods, and used in glutamate flavorings such as MSG. In highly alcaline solutions the doubly negative anion OOC-CH(NH
2
)-(CH
2
)2-COO prevails.


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