gamma-laevo-glutamyl-laevo-glutamic acid
L-g-glutamyl-L-glutamic acid
 
Notes:
an endogenous dipeptide in the rat olfactory bulb which activates n-methyl-d-aspartate receptors. gammaGlutamylglutamic acid is made of two glutamic acid molecules. 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. 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. 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. Glutamate transporters 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: * Damage to mitochondria from excessively high intracellular Ca2+. * 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. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing 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. (http://en.wikipedia.org/wiki/Glutamic_acid) [HMDB]
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      1116-22-9 gamma-L-Glutamyl-L-glutamic acid
       
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CAS Number: 1116-22-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 214-233-2
FDA UNII: 6018KCN7X2
Nikkaji Web: J203.335F
XlogP3-AA: -4.30 (est)
Molecular Weight: 276.24592000
Formula: C10 H16 N2 O7
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 664.08 °C. @ 760.00 mm Hg (est)
Flash Point: 672.00 °F. TCC ( 355.40 °C. ) (est)
logP (o/w): -2.603 (est)
Soluble in:
 water, 8.444e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
gamma-L-Glutamyl-L-glutamic acid
Penta International
L-GLUTAMYL-L-GLUTAMIC ACID
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for gamma-laevo-glutamyl-laevo-glutamic acid usage levels up to:
 not for fragrance use.
 
Recommendation for gamma-laevo-glutamyl-laevo-glutamic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 92865
National Institute of Allergy and Infectious Diseases: Data
 (2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid
Chemidplus: 0001116229
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References:
 (2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 92865
Pubchem (sid): 135051189
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C05282
HMDB (The Human Metabolome Database): HMDB11737
FooDB: FDB028415
Export Tariff Code: 2924.10.1050
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid
g-L-glutamyl-L-glutamic acid
L-g-glutamyl-L-glutamic acid
N-gamma-l-glutamyl-L-glutamic acid
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Articles:
PubMed: Mass spectrometric and kinetic studies on slow progression of papain-catalyzed polymerization of L-glutamic acid diethyl ester.
PubMed: Monoclonal anti-dipeptide antibodies cross-react with detyrosinated and glutamylated forms of tubulins.
PubMed: Monoclonal antibody specific for carbodiimide-fixed glutamate: immunocytochemical localization in the rat CNS.
PubMed: The effects of carbamazepine and valproate on folate metabolism in man.
PubMed: Influx of two dipeptides, glycylsarcosine and L-glutamyl-L-glutamic acid, into hamster jejunum in vitro.
PubMed: Proposed structure for coenzyme F420 from Methanobacterium.
PubMed: Purification and properties of the dihydrofolate synthetase from Serratia indica.
PubMed: [Pterin chemistry. An unequivocal synthesis of pteroyl-gamma-L-glutamyl-gamma-L-glutamyl-L-glutamic acid].
PubMed: Depression of jejunal dipeptide transport by pyridoxine deficiency in the rat.
PubMed: Studies on a wide-spectrum intestinal dipeptide uptake system in the monkey and in the human.
PubMed: [Pterin chemistry. 45. A new and clear synthesis of isomer-free pteroyl-gamma-L-glutamyl-L-glutamic acid].
PubMed: [Study on gamma-blutamyl peptides. I. Isolation and identification of gamma-L-glutamyl-L-glutamic acid and gamma-L-glutamyl-L-glutamine from the bovine brain].
PubMed: ISOLATION OF GAMMA-L-GLUTAMYL-L-GLUTAMIC ACID AND GAMMA-L-GLUTAMYL-L-GLUTAMINE FROM BOVINE BRAIN.
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