NAAG
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MedKoo CAT#: 464491

CAS#: 3106-85-2

Description: α-NAAG is a peptide neurotransmitter that is widely expressed throughout mammalian central and peripheral nervous systems. Following synaptic release, α-NAAG activates postsynaptic metabotropic glutamate receptor 3 (mGluR3) to inhibit cAMP production in neurons and astrocytes, as well as acts on presynaptic mGluR3 to inhibit the release of amine neurotransmitters, including GABA and glutamate. Increasing α-NAAG levels via NAAG peptidase inhibition reduces trauma-induced excitotoxic cell death in a mouse model of traumatic brain injury, as well as reduces hyperalgesia in various rodent pain models and schizophrenia-like stereotypic behaviors induced by phencyclidine in rats. Tumor levels of α-NAAG are positively correlated with tumor grade in patients with gliomas and meningiomas.


Chemical Structure

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NAAG
CAS# 3106-85-2

Theoretical Analysis

MedKoo Cat#: 464491
Name: NAAG
CAS#: 3106-85-2
Chemical Formula: C11H16N2O8
Exact Mass: 304.0907
Molecular Weight: 304.255
Elemental Analysis: C, 43.42; H, 5.30; N, 9.21; O, 42.07

Price and Availability

Size Price Availability Quantity
10.0mg USD 230.0 2 Weeks
50.0mg USD 430.0 2 Weeks
100.0mg USD 700.0 2 Weeks
250.0mg USD 1200.0 2 Weeks
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Synonym: NAAG; α-NAAG; α NAAG; N-Acetylaspartylglutamic Acid; N Acetylaspartylglutamic Acid; α-Spaglumic Acid; α Spaglumic Acid;

IUPAC/Chemical Name: acetyl-L-aspartyl-L-glutamic acid

InChi Key: OPVPGKGADVGKTG-BQBZGAKWSA-N

InChi Code: 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)/t6-,7-/m0/s1

SMILES Code: OC(CC[C@H](NC([C@H](CC(O)=O)NC(C)=O)=O)C(O)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 65.7
DMSO 20.0 65.7
Ethanol 20.0 65.7
PBS (pH 7.2) 10.0 32.9

Preparing Stock Solutions

The following data is based on the product molecular weight 304.255 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Faull KF, Rafie R, Pascoe N, Marsh L, Pfefferbaum A. N-acetylaspartic acid (NAA) and N-acetylaspartylglutamic acid (NAAG) in human ventricular, subarachnoid, and lumbar cerebrospinal fluid. Neurochem Res. 1999 Oct;24(10):1249-61. doi: 10.1023/a:1020973023059. PMID: 10492520.

2: Ma D, Zhang J, Sugahara K, Ageta T, Nakayama K, Kodama H. Simultaneous determination of N-acetylaspartic acid, N-acetylglutamic acid, and N-acetylaspartylglutamic acid in whole brain of 3-mercaptopropionic acid-treated rats using liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Anal Biochem. 1999 Dec 15;276(2):124-8. doi: 10.1006/abio.1999.4352. PMID: 10603234.

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4: Avoli M, Barra PF, Brancati A, Cecchi L, Deodati M. Effetti degli acidi N-acetilaspartico ed N-acetilaspartilglutammico applicati iontoforeticamente in alcune strutture del nevrasse di ratto [Effects of N-acetylaspartic acid and N-acetylaspartylglutamic acid by iontophoretic administration, on some structures of the neuraxis in rats]. Boll Soc Ital Biol Sper. 1976 Sep 30;52(18):1525-30. Italian. PMID: 1024564.

5: van Bijsterveld OP, Aalders-Deenstra V. Klinische Erprobung von N-acetyl- aspartyl-Glutaminsäure Augentropfen bei subakuter und chronischer atopischer Konjunktivitis [Clinical evaluation of N-acetylaspartylglutamic acid eyedrops in subacute and chronic atopic conjunctivitis]. Klin Monbl Augenheilkd. 1986 Jun;188(6):625-7. German. doi: 10.1055/s-2008-1050733. PMID: 3093750.

6: Curatolo A, Brancati A. Sulla concentrazione encefalica degli acidi N-acetilaspartico e n-acetilaspartilglutammiico in animali trattati con iproniazide [On the cerebral concentration of N-acetylaspartic acid and N-acetylaspartylglutamic acid in animals treated with iproniazid]. Boll Soc Ital Biol Sper. 1967 Jun 15;43(11):652-4. Italian. PMID: 6073445.

7: Horak F. Seasonal allergic rhinitis. Newer treatment approaches. Drugs. 1993 Apr;45(4):518-27. doi: 10.2165/00003495-199345040-00004. PMID: 7684672.

8: Chen L, Chao Y, Cheng P, Li N, Zheng H, Yang Y. UPLC-QTOF/MS-Based Metabolomics Reveals the Protective Mechanism of Hydrogen on Mice with Ischemic Stroke. Neurochem Res. 2019 Aug;44(8):1950-1963. doi: 10.1007/s11064-019-02829-x. Epub 2019 Jun 24. PMID: 31236794.

9: van Vliet E, Eixarch E, Illa M, Arbat-Plana A, González-Tendero A, Hogberg HT, Zhao L, Hartung T, Gratacos E. Metabolomics reveals metabolic alterations by intrauterine growth restriction in the fetal rabbit brain. PLoS One. 2013 May 27;8(5):e64545. doi: 10.1371/journal.pone.0064545. PMID: 23724060; PMCID: PMC3664640.

10: Avoli M, Barra PF, Brancati A, Deodati M, Vagnozzi R. Studies about molluscan C.N.S.: ii) Changes induced by n-acetylaspartic acid, n-acetylaspartylglutamic acid and GABA in the activity of single identified neurones of Aplysia. Boll Soc Ital Biol Sper. 1977 Jul 15;53(13):1036-41. PMID: 597434.

11: Bérard PV, Bérard PV Jr, Mouillac-Gambarelli N, Jourdan-Fonta D. Conjonctivites allergiques saisonnières et chroniques chez l'adulte et l'enfant. Evaluation multicentrique du N.A.A.G.A. Collyre en pratique ophtalmologique et allergologique [Seasonal and chronic allergic conjunctivitis in adults with children. Multicenter evaluation of the collyrium N-acetylaspartylglutamic acid (NAAGA) in ophthalmologic and allergy practices]. Bull Soc Ophtalmol Fr. 1987 Apr;87(4):475-6, 479-83. French. PMID: 3652358.

12: Raider K, Ma D, Harris JL, Fuentes I, Rogers RS, Wheatley JL, Geiger PC, Yeh HW, Choi IY, Brooks WM, Stanford JA. A high fat diet alters metabolic and bioenergetic function in the brain: A magnetic resonance spectroscopy study. Neurochem Int. 2016 Jul;97:172-80. doi: 10.1016/j.neuint.2016.04.008. Epub 2016 Apr 26. PMID: 27125544; PMCID: PMC4900919.

13: Brandt AS, Unschuld PG, Pradhan S, Lim IA, Churchill G, Harris AD, Hua J, Barker PB, Ross CA, van Zijl PC, Edden RA, Margolis RL. Age-related changes in anterior cingulate cortex glutamate in schizophrenia: A (1)H MRS Study at 7 Tesla. Schizophr Res. 2016 Apr;172(1-3):101-5. doi: 10.1016/j.schres.2016.02.017. Epub 2016 Feb 28. PMID: 26925800; PMCID: PMC4821673.

14: Curatolo A, D'Arcangelo P, Lino A, Brancati A. Distribuzione degli acidi N-acetilaspartico e N-acetilaspartilglutammico nel nevrasse di uccelli [Distribution of N-acetylaspartic and N-acetylaspartylglutamic acids in the neuraxis of birds]. Boll Soc Ital Biol Sper. 1965 Jun 15;41(11):591-3. Italian. PMID: 5875910.

15: Reddy AV, Ravindranath B. Synthesis of alpha-, beta- and cyclic spaglumic acids. Int J Pept Protein Res. 1992 Nov;40(5):472-6. doi: 10.1111/j.1399-3011.1992.tb00326.x. PMID: 1362393.

16: Bradley AJ, Read BL, Levin E, Devine DV. Small-molecule complement inhibitors cannot prevent the development of the platelet storage lesion. Transfusion. 2008 Apr;48(4):706-14. doi: 10.1111/j.1537-2995.2007.01595.x. Epub 2008 Jan 7. PMID: 18194377.

NAAG

10.0mg / USD 230.0