L-Glutamic acid-[1,2-13C2]
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L-Glutamic acid-[1,2-13C2]

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L-Glutamic acid-[1,2-13C2] is a labelled L-Glutamic acid. Glutamic acid is a non-essential amino acid that acts as an excitatory neurotransmitter in the CNS.

Category
BOC-Amino Acids
Catalog number
BAT-002771
Molecular Formula
C3[13C]2H9NO4
Molecular Weight
149.11
L-Glutamic acid-[1,2-13C2]
IUPAC Name
(2S)-2-amino(1,2-13C2)pentanedioic acid
Synonyms
(2R)-2-aminopentanedioic acid-13C2
Related CAS
56-86-0 (unlabelled)
Appearance
White powder
Purity
98% by HPLC; 99% atom 13C
Density
1.1452 g/cm3(rough estimate)
Melting Point
60-80 °C
Boiling Point
473.68°C (rough estimate)
Storage
Store at 2-8°C
InChI
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1/i1+1,2+1
InChI Key
WHUUTDBJXJRKMK-JBAKHTSASA-N
Canonical SMILES
C(CC(=O)O)C(C(=O)O)N

L-Glutamic acid-[1,2-13C2] is an isotopically labeled form of L-glutamic acid in which the first and second carbon atoms are enriched with the stable carbon-13 isotope. This labeled compound retains the structural and chemical properties of natural L-glutamic acid but is distinguishable through advanced analytical techniques like nuclear magnetic resonance (NMR) and mass spectrometry (MS). Its unique labeling makes it a valuable tool in biochemical research and various industrial applications.

One primary application of L-Glutamic acid-[1,2-13C2] is in metabolic tracing studies. By incorporating the labeled molecule into biological systems, researchers can track its metabolic pathways and quantify fluxes in processes like the tricarboxylic acid (TCA) cycle and glutamate metabolism. This is crucial for understanding cellular energy production and metabolic regulation.

In drug development, L-Glutamic acid-[1,2-13C2] is used to study the pharmacokinetics and dynamics of glutamate-related drugs. Its isotopic label allows precise monitoring of drug interactions with glutamate receptors, transporters, or enzymes, aiding in the design of novel therapies for neurological disorders and cancer.

L-Glutamic acid-[1,2-13C2] is also employed in protein structure and function studies. As a key component of proteins, labeled glutamic acid can be incorporated into specific residues, enabling detailed analysis of protein folding, dynamics, and interactions using NMR spectroscopy.

Additionally, this compound is valuable in agricultural and environmental research. It helps in studying soil nitrogen cycling, plant nitrogen uptake, and microbial interactions. The isotopic labeling provides insights into the roles of glutamic acid in ecosystem processes, contributing to advancements in sustainable agriculture and environmental conservation.

1.Multidrug resistance P-glycoprotein dampens SR-BI cholesteryl ester uptake from high density lipoproteins in human leukemia cells.
Spolitu S1, Uda S1, Deligia S1, Frau A1, Collu M2, Angius F1, Batetta B1. Am J Cancer Res. 2016 Feb 15;6(3):615-27. eCollection 2016.
Tumor cells are characterised by a high content of cholesterol esters (CEs), while tumor-bearing patients show low levels of high-density lipoproteins (HDLs). The origin and significance of high CE levels in cancer cell biology has not been completely clarified. Recent evidence that lymphoblastic cells selectively acquire exogenous CE from HDL via the scavenger receptor SR-BI has drawn attention to the additional membrane proteins involved in this pathway. P-glycopotein-MDR1 (P-gp) is a product of the MDR1 gene and confers resistance to antitumor drugs. Its possible role in plasma membrane cholesterol trafficking and CE metabolism has been suggested. In the present study this aspect was investigated in a lymphoblastic cell line selected for MDR1 resistance. CEM were made resistant by stepwise exposure to low (LR) and high (HR) doses of vincristine (VCR). P-gp activity ((3)H-vinblastine), CE content, CE and triglycerides (TG) synthesis ((14)C-oleate), neutral lipids and Dil-HDL uptake (fluorescence), SR-BI, ABCA1 and P-gp protein expression (western blotting) were determined.
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