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A5930

Sigma-Aldrich

N-Acetyl-Asp-Glu

≥97% (TLC)

Synonym(s):

N-Acetylaspartylglutamicacid, NAAG, Spaglumic acid

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About This Item

Empirical Formula (Hill Notation):
C11H16N2O8
CAS Number:
3106-85-2
Molecular Weight:
304.25
MDL number:
MFCD00076652
UNSPSC Code:
12352209
PubChem Substance ID:
24891036
NACRES:
NA.32

Quality Level

200

assay

≥97% (TLC)

form

powder or crystals

optical activity

[α]22/D −34.5°, c = 1.1 in H2O(lit.)

storage condition

(Tightly closed. Dry)

color

white to off-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

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)

InChI key

OPVPGKGADVGKTG-UHFFFAOYSA-N

Gene Information

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

General description

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.

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Store desiccated.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Preparation and affinity identification of glutamic acid-urea small molecule analogs in prostate cancer
Zhang Z, et al.
Oncology Letters, 12(2), 1001-1006 (2016)
Hyeong Hun Lee et al.
Magnetic resonance in medicine, 82(1), 33-48 (2019-03-13)
To develop a robust method for brain metabolite quantification in proton magnetic resonance spectroscopy (1 H-MRS) using a convolutional neural network (CNN) that maps in vivo brain spectra that are typically degraded by low SNR, line broadening, and spectral baseline
Yan Zhang et al.
Magnetic resonance in medicine, 66(2), 307-313 (2011-06-10)
This article introduces regularized lineshape deconvolution in conjunction with TE-averaged PRESS spectroscopy to measure N-acetyl-aspartyl-glutamate (NAAG). Averaging different echo times suppressed the signals of multiplets from strongly coupled spin systems near 2 ppm; thus, minimizing the interfering signals to detect
Richard Bergeron et al.
Current medicinal chemistry, 19(9), 1360-1364 (2012-02-07)
At central synapses, glutamate is the main excitatory neurotransmitter. Once released from presynaptic terminals, glutamate activates a number of different glutamatergic receptors one of which is the ligand gated ionophore glutamatergic subtype N-methyl-D-aspartate receptors (NMDARs). NMDARs play a crucial role
Rosane Gomez et al.
Biological psychiatry, 71(3), 239-246 (2011-08-23)
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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