| Size | Price | Stock | Qty |
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| 500mg |
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| 1g |
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| 2g |
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| 5g |
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| 10g |
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| 50g |
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Purity: ≥98%
D-glutamine (also known as H-D-Gln-OH), an unnatural isomer of glutamine, is a D type stereoisomer of glutamine which is one of the 20 amino acids encoded by the standard genetic code. In catabolic states of injury and illness, glutamine becomes conditionally-essential (requiring intake from food or supplements). Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body and one of the few amino acids that can directly cross the blood–brain barrier. Glutamine is a key pharmaconutrient in the body's response to stress and injury.
| Targets |
Endogenous Metabolite
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| ln Vitro |
In the glutamate/GABA-glutamine cycle (GGC), glutamine is a crucial amino acid in the central nervous system (CNS). In order to replenish the pools of excitatory and inhibitory neurotransmitters, glutamine is moved from astrocytes to neurons in the GGC[1]. The function of D-glutamine in providing protection against acetaldehyde-induced disruption of barrier function in Caco-2 cell monolayer has been investigated. The Caco-2 cell monolayer is used to assess the role of glutamine in shielding the intestinal epithelium from acetaldehyde-induced loss of barrier function. In a time- and dose-dependent way, L-glutamine mitigated the acetaldehyde-induced decrease in transepithelilal electrical resistance and increase in permeability to inulin and lipopolysaccharide; no discernible protection was produced by D-glutamine, L-aspargine, L-arginine, L-lysine, or L-alanine. Additionally, acetaldehyde-induced TER drop and inulin flux increase are not affected by D-glutamine. Glutaminase or D-glutamine as an inhibitor did not affect TER or inulin flow in cell monolayers treated with acetaldehyde or left in control. The fact that D-glutamine has no effect on acetaldehyde protection suggests that L-glutamine mediates stereospecific protection[2].
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| ln Vivo |
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| Enzyme Assay |
Glutamine is a key amino acid in the CNS, playing an important role in the glutamate/GABA-glutamine cycle (GGC). In the GGC, glutamine is transferred from astrocytes to neurons, where it will replenish the inhibitory and excitatory neurotransmitter pools. Different transporters participate in this neural communication, i.e., the transporters responsible for glutamine efflux from astrocytes and influx into the neurons, such as the members of the SNAT, LAT, y+LAT, and ASC families of transporters. The SNAT family consists of the transporter isoforms SNAT3 and SNAT5 that are related to efflux from the astrocytic compartment, and SNAT1 and SNAT2 that are associated with glutamine uptake into the neuronal compartment. The isoforms SNAT7 and SNAT8 do not have their role completely understood, but they likely also participate in the GGC. The isoforms LAT2 and y+LAT2 facilitate the exchange of neutral amino acids and cationic amino acids (y+LAT2 isoform) and have been associated with glutamine efflux from astrocytes. ASCT2 is a Na+-dependent antiporter, the participation of which in the GGC also remains to be better characterized. All these isoforms are tightly regulated by transcriptional and translational mechanisms, which are induced by several determinants such as amino acid deprivation, hormones, pH, and the activity of different signaling pathways. Dysfunctional glutamine transporter activity has been associated with the pathophysiological mechanisms of certain neurologic diseases, such as Hepatic Encephalopathy and Manganism. However, there might also be other neuropathological conditions associated with an altered GGC, in which glutamine transporters are dysfunctional. Hence, it appears to be of critical importance that the physiological and pathological aspects of glutamine transporters are thoroughly investigated[1].
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| Cell Assay |
Role of L-glutamine in the protection of intestinal epithelium from acetaldehyde-induced disruption of barrier function was evaluated in Caco-2 cell monolayer. L-Glutamine reduced the acetaldehyde-induced decrease in transepithelilal electrical resistance and increase in permeability to inulin and lipopolysaccharide in a time- and dose-dependent manner; d-glutamine, L-aspargine, L-arginine, L-lysine, or L-alanine produced no significant protection. The glutaminase inhibitor 6-diazo-5-oxo-L-norleucine failed to affect the L-glutamine-mediated protection of barrier function. L-Glutamine reduced the acetaldehyde-induced redistribution of occludin, zonula occludens-1 (ZO-1), E-cadherin, and beta-catenin from the intercellular junctions. Acetaldehyde dissociates occludin, ZO-1, E-cadherin, and beta-catenin from the actin cytoskeleton, and this effect was reduced by L-glutamine. L-Glutamine induced a rapid increase in the tyrosine phosphorylation of EGF receptor, and the protective effect of L-glutamine was prevented by AG1478, the EGF-receptor tyrosine kinase inhibitor. These results indicate that L-glutamine prevents acetaldehyde-induced disruption of the tight junction and increase in the paracellular permeability in Caco-2 cell monolayer by an EGF receptor-dependent mechanism[2].
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| Animal Protocol |
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| References |
[1]. Leke R, et al. The Glutamine Transporters and Their Role in the Glutamate/GABA-Glutamine Cycle. Adv Neurobiol. 2016;13:223-257.
[2]. Seth A, et al. L-Glutamine ameliorates acetaldehyde-induced increase in paracellular permeability in Caco-2 cellmonolayer. Am J Physiol Gastrointest Liver Physiol. 2004 Sep;287(3):G510-7 |
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| Additional Infomation |
D-glutamine is the D-enantiomer of glutamine. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a glutamine. It is a conjugate base of a D-glutaminium. It is a conjugate acid of a D-glutaminate. It is an enantiomer of a L-glutamine. It is a tautomer of a D-glutamine zwitterion.
A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. D-Glutamine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-glutamine is a natural product found in Daphnia pulex and Homo sapiens with data available. A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells. |
| Molecular Formula |
C5H10N2O3
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| Molecular Weight |
146.14
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| Exact Mass |
146.06913
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| Elemental Analysis |
C, 41.09; H, 6.90; N, 19.17; O, 32.84
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| CAS # |
5959-95-5
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| Related CAS # |
DL-Glutamine;6899-04-3;L-Glutamine;56-85-9
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| PubChem CID |
145815
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| Appearance |
Typically exists as white to off-white solids at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
353.5±52.0 °C at 760 mmHg
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| Melting Point |
185ºC
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| Flash Point |
167.6±30.7 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.564
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| LogP |
-1.28
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| tPSA |
106.41
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| SMILES |
N[ C@H](CCC(N)=O)C(O)=O
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| InChi Key |
ZDXPYRJPNDTMRX-GSVOUGTGSA-N
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| InChi Code |
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1
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| Chemical Name |
(2R)-2,5-diamino-5-oxopentanoic acid
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 12.5 mg/mL (85.53 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.8428 mL | 34.2138 mL | 68.4275 mL | |
| 5 mM | 1.3686 mL | 6.8428 mL | 13.6855 mL | |
| 10 mM | 0.6843 mL | 3.4214 mL | 6.8428 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
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