FComEx: L-Glutamic acid (PC000030)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:32 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000030

FoodDB Record

FDB012535

Chemical Information

Name

L-Glutamic acid

Description

L-glutamic acid (abbreviated Glu or E), also referred to as glutamate (the anion), is a non-essential amino acid, one of the 20 amino acids used in the biosynthesis of proteins. L-glutamic acid exists in all living species, from bacteria to humans. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is a component amino acid in many protein rich foods including the gluten protein in flour and is found as a free acid in cheeses and soya sauce. It is used as a flavor enhancer as a sodium salt known as monosodium glutamate. Glutamate is a key molecule in cellular metabolism. 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 N-methyl-d-aspartate acid (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. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, glutamate can accumulate outside cells, causing glutamate excitotoxicity. Excitotoxicity occurs when neurons are exposed to high levels of glutamate or other neurotransmitters, causing persistent activation of the and Œ±-amino-3-hydroxy-5-methylisoxazole propionic acid (AMPA) receptors and voltage-gated calcium channels. This results in a lethal influx of extracellular calcium leading to neuronal damage and eventual cell death. Cell death arises from damage to mitochondria by the excessively high intracellular calcium, which open mitochondrial pores, causing mitochondria to swell. Reactive oxygen species (ROS) may also be released by mitochondria into the intracellular space. Excess glutamate and calcium trigger apoptosis by further activating transcription factors for pro-apoptotic genes, or downregulating transcription factors for anti-apoptotic genes. Glutamate excitotoxicity causes other health consequences. In ischemic stroke and brain trauma, the severely reduced blood supply leads to flooding of glutamate and aspartate into the extra-neuronal space ( PMID: 16314180). Glutamate excitotoxicity is associated with diseases like amyotrophic lateral sclerosis, multiple sclerosis, lathyrism, and Alzheimer's disease (PMID: 20229265) and in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart which is like a paroxysmal depolarizing shift seen 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. Moreover, glutamic acid is associated with N-acetylglutamate synthetase deficiency, which is an inborn error of metabolism.

CAS Number

56-86-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(2S)-2-Aminopentanedioate	HMDB
(2S)-2-Aminopentanedioic acid	HMDB
(S)-(+)-Glutamate	HMDB
(S)-(+)-Glutamic acid	HMDB
(S)-2-Aminopentanedioate	Generator
(S)-2-Aminopentanedioic acid	ChEBI
(S)-Glutamate	Generator
(S)-Glutamic acid	ChEBI
α-aminoglutaric acid, (S)-	biospider
α-glutamic acid, (S)-	biospider
1-Aminopropane-1,3-dicarboxylic acid	HMDB
2-Aminoglutaric acid, (S)-	biospider
a-aminoglutaric acid, (S)-	biospider
a-glutamic acid, (S)-	biospider
Acide glutamique	ChEBI
Acido glutamico	ChEBI
Alpha-aminoglutarate, (S)-	biospider
Alpha-aminoglutaric acid, (S)-	biospider
Alpha-glutamate, (S)-	biospider
Alpha-glutamic acid, (S)-	biospider
E	ChEBI
Glutamic acid; L-form	db_source
Glutaminol	HMDB
Glutaton	HMDB
L (+)-glutamic acid, alpha-form	biospider
L-(+)-Glutamate	HMDB
L-(+)-Glutamic acid	HMDB
L-a-Aminoglutarate	HMDB
L-a-Aminoglutaric acid	HMDB
L-alpha-Aminoglutarate	HMDB
L-alpha-Aminoglutaric acid	HMDB
L-Glu	ChEBI
L-Glutamate	Generator
L-glutamic acid	manual
L-Glutaminic acid	ChEBI
L-Glutaminsaeure	ChEBI
S-1-Aminopropane-1,3-dicarboxylate	biospider

Chemical Formula

C5H9NO4

IUPAC name

(2S)-2-aminopentanedioic acid

InChI Identifier

InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1

InChI Key

WHUUTDBJXJRKMK-VKHMYHEASA-N

Isomeric SMILES

N[C@@H](CCC(O)=O)C(O)=O

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16015 )
L-alpha-amino acid (CHEBI:16015 )
glutamic acid (CHEBI:16015 )
glutamine family amino acid (CHEBI:16015 )
Common amino acids (C00025 )
Amino acids (C00025 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-3.69	HANSCH,C ET AL. (1995)
Experimental Water Solubility	8.57 mg/mL at 25 oC	BULL,HB et al. (1978)
Melting Point	Mp 224-225 (211-213°, 247-249°)° dec.	DFC

Foods of Origin