L-Aspartyl-L-glutamic acid
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| Category | Others |
| Catalog number | BBF-05697 |
| CAS | 6157-06-8 |
| Molecular Weight | 262.22 |
| Molecular Formula | C9H14N2O7 |
| Purity | ≥95% by HPLC |
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Description
L-Aspartyl-L-glutamic acid is a dipeptide composed of aspartic acid and glutamic acid. It is an incomplete breakdown product of protein digestion or protein catabolism.
Specification
| Synonyms | Aspartyl-glutamate; H-DE-OH; L-alpha-Aspartyl-L-glutamic acid; Asp-glu; Aspartylglutamate; alpha-aspartylglutamic acid; N-(2-Amino-3-carboxy-1-hydroxypropylidene)glutamic acid; (S)-2-((S)-2-amino-3-carboxypropanamido)pentanedioic acid |
| Sequence | H-Asp-Glu-OH |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]pentanedioic acid |
| Canonical SMILES | C(CC(=O)O)C(C(=O)O)NC(=O)C(CC(=O)O)N |
| InChI | InChI=1S/C9H14N2O7/c10-4(3-7(14)15)8(16)11-5(9(17)18)1-2-6(12)13/h4-5H,1-3,10H2,(H,11,16)(H,12,13)(H,14,15)(H,17,18)/t4-,5-/m0/s1 |
| InChI Key | CKAJHWFHHFSCDT-WHFBIAKZSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 647.8±55.0°C (Predicted) |
| Melting Point | 150-155°C |
| Density | 1.530±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Water |
Reference Reading
1. Development, validation, and application of a surrogate analyte method for determining N-acetyl-l-aspartyl-l-glutamic acid levels in rat brain, plasma, and cerebrospinal fluid
Kohnosuke Kinoshita, Kotaro Arai, Kazuaki Kawaura, Tetsuaki Hiyoshi, Jun-ichi Yamaguchi J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:1-11. doi: 10.1016/j.jchromb.2015.09.005. Epub 2015 Sep 10.
A bioanalytical strategy for the simple and accurate determination of endogenous substances in a variety of biological matrices using liquid chromatography-tandem mass spectrometry is described. The robust method described here uses two stable isotope-labeled compounds as a surrogate analyte and an internal standard to construct calibration curves with authentic matrices that can be applied to determine N-acetyl-l-aspartyl-l-glutamic acid (NAAG) levels in rat brain, plasma, and cerebrospinal fluid (CSF) using a simple extraction and with a short analysis time of 4min. The validated lower limits of quantification were 1.00nmol/g for brain and 0.0100nmol/mL for plasma and CSF. Using this method, regional differences in NAAG levels in the brain as well as plasma and CSF levels that were much lower than those in the brain were successfully confirmed in treatment-naïve rats. Moreover, after the rats were treated with the intraventricular administration of a NAAG peptidase inhibitor, the NAAG levels increased rapidly and dramatically in the CSF and slightly in the plasma in a time-dependent manner, while the brain levels were not affected. Thus, the procedure described here was easily applied to the determination of NAAG in different matrices in the same manner as that used for xenobiotics, and this method would also be easily applicable to the accurate measurement of endogenous substances in a variety of biological matrices.
2. Synthesis of N-acetyl-l-aspartyl-l-glutamic acid; [3 H]NAAG
Michal Kriegelstein, Aleš Marek J Labelled Comp Radiopharm. 2022 Jul;65(9):244-253. doi: 10.1002/jlcr.3991. Epub 2022 Jul 21.
[3 H]NAAG, N-acetyl-l-aspartyl-l-glutamic acid, has been widely used as a substrate in glutamate carboxypeptidase II (GCPII) reactions, either to determine the inhibitory constants at 50% inhibition (IC50 ) of novel compounds or to measure GCPII activities in different tissues harvested from various disease models. The importance of [3 H]NAAG, combined with its current commercial unavailability, prompted the development of a reliable eight-step synthetic procedure towards [3 H2 ]NAAG starting from commercially available pyroglutamate. Pure [3 H]NAAG of high molar activity (49.8 Ci/mmol) and desired stereochemistry was isolated in high radiochemical yield (67 mCi) and radiochemical purity (>99%). The identity was confirmed by mass spectrometry and co-injection with unlabeled reference.
3. 1H-NMR, 1H-NMR T2-edited, and 2D-NMR in bipolar disorder metabolic profiling
Sumit Sethi, Mariana Pedrini, Lucas B Rizzo, Maiara Zeni-Graiff, Caroline Dal Mas, Ana Cláudia Cassinelli, Mariane N Noto, Elson Asevedo, Quirino Cordeiro, João G M Pontes, Antonio J M Brasil, Acioly Lacerda, Mirian A F Hayashi, Ronei Poppi, Ljubica Tasic, Elisa Brietzke Int J Bipolar Disord. 2017 Dec;5(1):23. doi: 10.1186/s40345-017-0088-2. Epub 2017 Jun 4.
Background: The objective of this study was to identify molecular alterations in the human blood serum related to bipolar disorder, using nuclear magnetic resonance (NMR) spectroscopy and chemometrics. Methods: Metabolomic profiling, employing 1H-NMR, 1H-NMR T2-edited, and 2D-NMR spectroscopy and chemometrics of human blood serum samples from patients with bipolar disorder (n = 26) compared with healthy volunteers (n = 50) was performed. Results: The investigated groups presented distinct metabolic profiles, in which the main differential metabolites found in the serum sample of bipolar disorder patients compared with those from controls were lipids, lipid metabolism-related molecules (choline, myo-inositol), and some amino acids (N-acetyl-L-phenyl alanine, N-acetyl-L-aspartyl-L-glutamic acid, L-glutamine). In addition, amygdalin, α-ketoglutaric acid, and lipoamide, among other compounds, were also present or were significantly altered in the serum of bipolar disorder patients. The data presented herein suggest that some of these metabolites differentially distributed between the groups studied may be directly related to the bipolar disorder pathophysiology. Conclusions: The strategy employed here showed significant potential for exploring pathophysiological features and molecular pathways involved in bipolar disorder. Thus, our findings may contribute to pave the way for future studies aiming at identifying important potential biomarkers for bipolar disorder diagnosis or progression follow-up.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
