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G-Glu-Ala

Alias: gamma-Glutamyl-L-alanine; G-Glu-Ala; G-Glu-Ala
Cat No.:V21565 Purity: ≥98%
γ-L-Glutamyl-L-alanine is composed of γ-glutamyl and alanine and is a proteolytic breakdown product of larger proteins.
G-Glu-Ala
G-Glu-Ala Chemical Structure CAS No.: 5875-41-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
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Product Description
γ-L-Glutamyl-L-alanine is composed of γ-glutamyl and alanine and is a proteolytic breakdown product of larger proteins. γ-L-Glutamyl-L-alanine is the natural substrate of γ-Glutamylcyclotransferase. γ-L-Glutamyl-L-alanine is a positive modulator of calcium-sensing receptor (CaR) function.
G-Glu-Ala (CAS#: 5875-41-2) is a dipeptide composed of glutamic acid (Glu) and alanine (Ala) linked by a gamma-peptide bond. It is also known as gamma-glutamyl-alanine. As a gamma-glutamyl dipeptide, it is a substrate for gamma-glutamyltransferase (GGT) and plays a role in the gamma-glutamyl cycle, which is involved in amino acid transport and glutathione metabolism. The compound is a metabolite and may be involved in various biological processes.
Biological Activity I Assay Protocols (From Reference)
Targets
G-Glu-Ala targets gamma-glutamyltransferase (GGT), an enzyme that catalyzes the transfer of the gamma-glutamyl group from glutathione and other gamma-glutamyl compounds to acceptors. As a gamma-glutamyl dipeptide, G-Glu-Ala is a substrate for GGT, and its hydrolysis or transfer reactions contribute to the gamma-glutamyl cycle. This cycle plays a role in amino acid transport across cell membranes and in glutathione homeostasis.
ln Vitro
γ-L-glutamyl-L-alanine (γ-Glu-Ala) has an EC50 of 4.8 µM and demonstrates Ca2+i mobilization potency in HEK-293 cells expressing CaR (calcium-sensing receptor)[3]. In human parathyroid cells, γ-L-glutamyl-L-alanine exhibits potency in Ca2+i mobilization, with an EC50 of 13.9 µM [3]. Normal human parathyroid cells' secretion of PTH is inhibited by γ-L-glutamyl-L-alanine (20 μM) [3]. A substrate of glutaminase B is γ-L-glutamyl-L-alanine [4].
In vitro, G-Glu-Ala functions as a substrate for gamma-glutamyltransferase, and its hydrolysis can be measured in enzymatic assays. The compound's role in the gamma-glutamyl cycle has been characterized in biochemical studies. Its effects on glutathione metabolism and amino acid transport have been investigated in various in vitro systems. The compound's specific biological activities are related to its role as a metabolite.
ln Vivo
In vivo, G-Glu-Ala is involved in the gamma-glutamyl cycle and amino acid metabolism. As a gamma-glutamyl dipeptide, it participates in the transport of amino acids across cell membranes and in the metabolism of glutathione. Its presence in biological fluids reflects the activity of the gamma-glutamyl cycle. Specific in vivo effects are related to its role as a metabolite rather than a pharmacological agent.
Enzyme Assay
In vitro enzyme assays for G-Glu-Ala involve measuring its hydrolysis or transfer by gamma-glutamyltransferase using purified enzyme preparations. The compound is incubated with GGT, and the release of glutamic acid or the transfer of the gamma-glutamyl group to acceptors is measured spectrophotometrically or by HPLC. These assays provide quantitative data on the compound's interactions with GGT.
Cell Assay
In vitro cell-based assays for G-Glu-Ala involve treating cells with the compound to assess its effects on glutathione metabolism, amino acid transport, and gamma-glutamyltransferase activity. Cellular glutathione levels are measured using biochemical assays. Amino acid transport is assessed using radiolabeled amino acids. These studies characterize the compound's role in cellular metabolism.
Animal Protocol
In vivo animal experiments for G-Glu-Ala have not been extensively reported. As a naturally occurring metabolite, its effects are studied primarily in the context of amino acid metabolism and the gamma-glutamyl cycle. Animal models of metabolic disorders may be used to study the compound's role in pathophysiology. Specific in vivo studies are limited in the available literature.
ADME/Pharmacokinetics
G-Glu-Ala has a molecular weight and formula consistent with glutamic acid-alanine dipeptides. As a gamma-glutamyl dipeptide, it is water-soluble and can be found in biological fluids. Its pharmacokinetic properties are characteristic of small peptides and amino acid derivatives. The compound's stability in biological fluids and its detection methods have been established for research purposes.
Toxicity/Toxicokinetics
G-Glu-Ala is a naturally occurring metabolite involved in the gamma-glutamyl cycle. As such, it is generally considered to have a favorable safety profile. However, comprehensive toxicological studies would be required for any therapeutic applications. Standard safety precautions should be taken when handling the compound in research settings.
References

[1]. Structure of a polysaccharide from Providencia rustigianii O11 containing a novel amide of 2-acetamido-2-deoxygalacturonic acid with L-glutamyl-L-alanine. Carbohydr Res. 2012 Feb 15;349:95-102.

[2]. gamma-Glutamylcyclotransferase: inhibition by D-beta-aminoglutaryl-L-alanine and analysis of the solvent kinetic isotope effect. Eur J Biochem. 1989 Sep 1;184(1):97-101.

[3]. Allosteric modulation of the calcium-sensing receptor by gamma-glutamyl peptides: inhibition of PTH secretion, suppression of intracellular cAMP levels, and a common mechanism of action with L-amino acids. J Biol Chem. 2011 Mar 18;286(11):8786-97.

[4]. Further Characterization of Glutaminase Isozymes from Pseudomonas aeruginosa.

Additional Infomation
γ-Glutamic acid (Gamma-Glu-Ala) is formed by the condensation of the γ-carboxyl group of L-glutamic acid and the amino group of L-alanine. It is a metabolite of both Saccharomyces cerevisiae and plants. It is the conjugate acid of γ-glutamyl alamic acid (1-). γ-Glutamic acid has been reported to exist in Homo sapiens, Iridum iris, and other organisms with relevant data. L-γ-Glutamic-L-alanine is a metabolite found or produced in Saccharomyces cerevisiae.
G-Glu-Ala (gamma-glutamyl-alanine) is a dipeptide composed of glutamic acid and alanine linked by a gamma-peptide bond. It is a substrate for gamma-glutamyltransferase and plays a role in the gamma-glutamyl cycle, which is involved in amino acid transport and glutathione metabolism. The compound is a metabolite and is involved in various biological processes related to amino acid metabolism.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H14N2O5
Molecular Weight
218.21
Exact Mass
218.09
CAS #
5875-41-2
PubChem CID
440103
Appearance
White to off-white solid powder
Density
1.362g/cm3
Boiling Point
564.4ºC at 760mmHg
Melting Point
188-192ºC(lit.)
Flash Point
295.1ºC
Index of Refraction
1.527
LogP
-3.8
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
6
Heavy Atom Count
15
Complexity
266
Defined Atom Stereocenter Count
2
SMILES
C[C@@H](C(=O)O)NC(=O)CC[C@@H](C(=O)O)N
InChi Key
WQXXXVRAFAKQJM-WHFBIAKZSA-N
InChi Code
InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
Chemical Name
(2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
Synonyms
gamma-Glutamyl-L-alanine; G-Glu-Ala; G-Glu-Ala
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ≥ 50 mg/mL (~229.14 mM)
DMSO : ~1 mg/mL (~4.58 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (458.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5827 mL 22.9137 mL 45.8274 mL
5 mM 0.9165 mL 4.5827 mL 9.1655 mL
10 mM 0.4583 mL 2.2914 mL 4.5827 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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