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A5930

Sigma-Aldrich

N-Acetyl-Asp-Glu

≥97% (TLC)

Synonyme(s) :

N-Acetylaspartylglutamicacid, NAAG, Spaglumic acid

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About This Item

Formule empirique (notation de Hill):
C11H16N2O8
Numéro CAS:
3106-85-2
Poids moléculaire :
304.25
Numéro MDL:
MFCD00076652
Code UNSPSC :
12352209
ID de substance PubChem :
24891036
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Pureté

≥97% (TLC)

Forme

powder or crystals

Activité optique

[α]22/D −34.5°, c = 1.1 in H2O(lit.)

Conditions de stockage

(Tightly closed. Dry)

Couleur

white to off-white

Solubilité

H2O: 50 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O

InChI

1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)

Clé InChI

OPVPGKGADVGKTG-UHFFFAOYSA-N

Informations sur le gène

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRIN3A(116443) , GRIN3B(116444) , GRINA(2907) , GRM3(2913)
mouse ... GRIN1(14810) , GRIN2A(14811) , GRIN2B(14812) , GRIN2C(14813) , GRIN2D(14814) , GRIN3A(242443) , GRIN3B(170483) , GRINA(66168) , GRM3(108069)
rat ... GRIN1(24408) , GRIN2A(24409) , GRIN2B(24410) , GRIN2C(24411) , GRIN2D(24412) , GRIN3A(191573) , GRIN3B(170796) , GRINA(266668) , GRM3(24416)

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Amino Acid Sequence

NAc-Asp-Glu

Description générale

Research area: Neuroscience

Application

N-Acetyl-Asp-Glu has been used in N-acetylated α-linked acidic dipeptidase (NAALADase) assay and affinity experiments.. It has also been used as a metabolite standard in liquid chromatography-mass spectrometry (LC-MS) targeted metabolomics analysis and mass-spectroscopy-based stable isotope-resolved metabolomics (SIRM) with 13C515N2-labeled-glutamine.

Actions biochimiques/physiologiques

Endogenous neurotransmitter localized to neurons with high affinity for metabotropic glutamate receptors, mGluR3. It is an antagonist at NMDA receptors. Catabolized by carboxypeptidase II, which is expressed on astrocyte membranes, to N-acetylaspartate and glutamate.
N-Acetyl-Asp-Glu (NAAG) is an abundant neuropeptide and neurotransmitter found in the mammalian brain. NAAG acts as an agonist for metabotropic glutamate receptors, mGluR3. In addition, it also acts as an antagonist for the N-methyl d-aspartate (NMDA) receptors. It yields N-acetyl aspartate and glutamate through glutamate carboxypeptidase II (GCP II) dependent pathway. Thus, it serves as a key glutamate reservoir in cancer cells. NAAG levels in plasma could be used as a non-invasive biomarker for tumor progression.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Attention

Store desiccated.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Ethanol modulates glutamate and γ-aminobutyric (GABA) function. However, little is known about the acute pharmacologic effects of ethanol on levels of GABA, glutamate, and other metabolites measurable in the human cortex in vivo with proton magnetic resonance spectroscopy ((1)H-MRS). Eleven
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