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Chemical Structure| 56-85-9 Chemical Structure| 56-85-9
Chemical Structure| 56-85-9

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L-Glutamine is an essential amino acid which serves as a substrate for biosynthesis of neurotransmitters glutamate and GABA in neurons.

Synonyms: L-Glutamine; NSC 27421; (S)-2,5-Diamino-5-Oxopentanoic Acid

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Product Citations

Product Citations

Aprajita Tripathi ; Debolina Dasgupta ; Anil Pant ; Ashlyn Bugbee ; Nanda Kumar Yellapu ; Ben H. Y. Choi , et al.

Abstract: Upon antigenic stimulation, CD4+T-cells undergo clonal expansion, elevating their bioenergetic demands and utilization of nutrients like glucose and glutamine. The nuclear factor erythroid 2-related factor 2 (Nrf2) is a well-known regulator of oxidative stress, but its involvement in modulating the metabolism of CD4+T-cells remains unexplored. Here, we elucidate the role of Nrf2 beyond the traditional antioxidation, in modulating activation-driven expansion of CD4+T-cells by influencing their nutrient metabolism. T-cell-specific activation of Nrf2 enhances early activation and IL-2 secretion, upregulates TCR-signaling, and increases activation-driven proliferation of CD4+T-cells. Mechanistically, high Nrf2 inhibits glucose metabolism through glycolysis but promotes glutamine metabolism via glutaminolysis to support increased T-cell proliferation. Further, Nrf2 expression is temporally regulated in activated CD4+T-cells with elevated expression during the early activation, but decreased expression thereafter. Overall, our findings uncover a novel role of Nrf2 as a metabolic modulator of CD4+T-cells, thus providing a framework for improving Nrf2-targeting therapies and T-cell immunotherapies.

Keywords: T-cell metabolism ; antioxidation ; adaptive immune cells ; T-cell activation

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Product Details of H-Gln-OH

CAS No. :56-85-9
Formula : C5H10N2O3
M.W : 146.14
SMILES Code : N[C@@H](CCC(N)=O)C(O)=O
Synonyms :
L-Glutamine; NSC 27421; (S)-2,5-Diamino-5-Oxopentanoic Acid
MDL No. :MFCD00008044
InChI Key :ZDXPYRJPNDTMRX-VKHMYHEASA-N
Pubchem ID :5961

Safety of H-Gln-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Gln-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 56-85-9 ]

[ 56-85-9 ] Synthesis Path-Downstream   1~11

  • 2
  • [ 56-85-9 ]
  • [ 75-04-7 ]
  • [ 56-86-0 ]
  • [ 3081-61-6 ]
  • 4
  • [ 56-85-9 ]
  • [ 72040-64-3 ]
  • (S)-4-Carbamoyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid [ No CAS ]
  • 5
  • [ 56-85-9 ]
  • [ 101-41-7 ]
  • [ 5959-95-5 ]
  • [ 28047-15-6 ]
  • 6
  • [ 56-85-9 ]
  • [ 557-66-4 ]
  • [ 3081-61-6 ]
YieldReaction ConditionsOperation in experiment
glutaminase; In water; at 30℃; for 22h;pH 11;Aqueous boric buffer; Example 1; Production of Theanine by an Enzymatic Method; 0.3 M glutamine and 1.5 M ethylamine hydrochloride in 0.05 M boric acid buffer (pH11) were reacted in the presence of 0.3 U glutaminase (commercial product) at 30 C. for 22 hours, and 225 nmol of L-theanine was obtained. Subsequently, the reaction solution was applied to Dowex 50×8 and Dowex 1×2 column chromatography (MUROMACHI CHEMICALS INC.), followed by ethanol treatment, to isolate the objective substance from the reaction solution. The isolated substance was analyzed by an amino acid analyzer (Hitachi, Ltd.) and paper chromatography, and was confirmed to be L-theanine due to the same pattern of movement as that of the standard substance. Hydrolysis treatment with hydrochloric acid or glutaminase produced glutamic acid and ethylamine at a ratio of 1:1. Thus, the isolated substance was hydrolyzed by glutaminase, demonstrating the binding of ethylamine at the gamma position of glutamic acid. L-glutamic acid generated by hydrolysis was confirmed by glutamate dehydrogenase. Thus, 8.5 g of L-theanine was obtained.
  • 7
  • [ 56-85-9 ]
  • [ 3081-61-6 ]
  • L-glutaminyl-L-theanine [ No CAS ]
  • L-theanyl-L-glutamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
glutaminase; In water; at 30℃; for 22h;pH 11;Aqueous boric buffer; Example 6; Production of a Mixture of Theanyl-Glutamine and Glutaminyl-Theanine; 0.4 M L-<strong>[3081-61-6]theanine</strong> and 0.4 M L-glutamine in 0.05 M boric acid buffer (ph11) were reacted in the presence of 0.3 U glutaminase (commercial product) at 30 C. for 22 hours to obtain 120 nmol of a mixture of theanyl-glutamine and glutaminyl-<strong>[3081-61-6]theanine</strong>. Subsequently, the reaction solution was applied to Dowex 50×8 and Dowex 1×2 column chromatography (MUROMACHI CHEMICALS INC.) to isolate the objective substance from the reaction solution. Structural analysis was conducted on the theanyl-glutamine and glutaminyl-<strong>[3081-61-6]theanine</strong> by mass spectrum analysis and NMR for confirmation.
  • 8
  • [ 56-85-9 ]
  • [ 593-51-1 ]
  • [ 56-86-0 ]
  • [ 3081-61-6 ]
YieldReaction ConditionsOperation in experiment
With glutaminase; water; boric acid; at 30℃; for 22h;pH 11;Enzymatic reaction; 0.3 M glutamine and 1.5 M methylamine hydrochloride were reacted in the presence of 0.3 U glutaminase (commercially available) at 30°C for 22 hours in a buffer solution of 0.05 M boric acid (pH 11), whereby 225 nm theanine was obtained. Reaction liquid was applied to Dowex 50.x.8 columnar chromatography and Dowex 1.x.2 columnar chromatography (both made by Muromachi Chemical Co., Ltd.) thereby to be processed by ethanol, whereby an object substance is isolated from the reaction liquid. As a result, 8.5 g theanine was obtained. The isolated substance was applied to an amino acid analyzer (made by Hitachi Co.) and paper chromatography. Since the isolated substance behaved in the same way as a standard substance, it was recognized as L-theanine. When the isolated substance was processed by hydrolysis using hydrochloric acid or glutaminase, glutamine acid and ethylamine were produced in a ratio of 1:1. Thus, since the isolated substance was hydrolyzed by glutaminase, it was shown that ethylamine was gamma-ethylamine of glutamine acid. Furthermore, it was confirmed on the basis of glutamate dehydrogenase that glutamine acid produced by hydrolysis was L-glutamine acid.
  • 9
  • [ 56-85-9 ]
  • [ 557-66-4 ]
  • [ 945623-40-5 ]
  • [ 3081-61-6 ]
YieldReaction ConditionsOperation in experiment
With glutaminase; at 30℃; for 22h;pH 11;borate buffer; Enzymatic reaction; By reacting 0.3M glutamine and 1.5M ethylamine hydrochloride in 0.05M borate buffer (pH 11) at 30°C for 22 hours under the presence of 0.3U glutaminase (commercially available product), 225nmol of theanine were obtained. The reaction solution was then subject to chromatography using Dowex 50 x 8 and Dowex 1 x 2 columns (both made by Muromachi Technos Co. , Ltd.) and to ethanol treatment to isolate the target substance from the reaction solution. 8.5g of theanine were thus obtained. The isolated substance was then subject to an amino acid analyzer (made by Hitachi, Ltd.) and paper chromatography and, by exhibition of the same behavior as a standard substance, was confirmed to be L-theanine. Upon hydrolytic treatment with hydrochloric acid or glutaminase, monosodium glutamate and ethylamine were produced at a ratio of 1:1. That the isolated substance is hydrolyzed by glutaminase indicates that ethylamine is bonded to the gamma position of monosodium glutamate. That the monosodium glutamate resulting from hydrolysis is the L-isomer was confirmed by means of monosodium glutamate dehydrogenase.
  • 10
  • [ 56-85-9 ]
  • [ 475-11-6 ]
  • C11H19N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.4% With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h; The <strong>[475-11-6]N-methyl-L-proline</strong> b (1.29 g, 10 mmol) was added to dichloromethane (20 mL),Add DCC (2.47g, 12mmol) and thenL-glutamine (1.46 g, 10 mmol),Reaction at room temperature for 24 hours, filtration,The mother liquor was concentrated to dryness to give a white solid, 1.5 g, yield 58.4%, that is compound B-3.
 

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