L-Glutamine [H-Gln-OH]

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Product Details
Synonyms	(+)-Glutamine; Levoglutamide; (S)-2,5-Diamino-5-oxopentanoic acid; L-Glutamic acid 5-amide; NSC 27421
Product Type	Chemical
Properties
Formula	C₅H₁₀N₂O₃
MW	146.1
CAS	56-85-9
RTECS	MA2275100
Purity Chemicals	≥99% (TLC)
Appearance	White to off-white powder.
Solubility	Soluble in water (30 mg/ml).
Other Product Data	Note: L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. The rate at which degradation proceeds is a function of time, temperature and pH. If used as a cell culture supplement, a 200mM stock solution (29.2mg/ml L-glutamine in 0.85% NaCl) can be prepared. The optimal concentration is dependent upon the cell type and medium used to culture the cells, but generally falls in the range of 2-6mM.
InChi Key	ZDXPYRJPNDTMRX-VKHMYHEASA-N
Smiles	NC(CC[C@H](N)C(O)=O)=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+20°C
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at +4°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Description

L-Glutamine is an amino acid and is essential in the formation of purine and pyrimidine nucleotides, amino sugars, glutathione, L-glutamate and other amino acids as well as in protein synthesis and glucose production.
It plays also a role in lipid synthesis (e.g. in cancer cells), cellular energy as a source next to glucose, nitrogen donation for many anabolic processes, including the synthesis of purines and carbon donation, as a source refilling the citric acid cycle. It is a nontoxic transporter of ammonia in the blood circulation and a precursor to the neurotransmitter glutamate and GABA.
L-Glutamine is an essential amino acid which is a crucial component of culture media that serves as a major energy source for cells in culture.
L-Glutamine exerts potent antioxidant and anti-inflammatory effects, next to its roles in cell proliferation and cancer. Levels of L-glutamine in human white adipose tissue (WAT) are linked with obesity-associated inflammation. Addition of L-glutamine in obese mice attenuated adipose tissue inflammation. Reduced L-glutamine levels during obesity shift the balance from glutaminolysis toward glycolysis, leading to nuclear O-GlcNAcylation, which activates inflammation.

Product References

Therapeutic considerations of L-glutamine: a review of the literature: A.L. Miller; Altern. Med. Rev. 4, 239 (1999) (Review)
Why is L-glutamine metabolism important to cells of the immune system in health, postinjury, surgery or infection? P. Newsholme; J. Nutr. 131, 2515S (2001) (Review)
Role of L-glutamine in critical illness: new insights: D. Kelly & P.E. Wischmeyer; Curr. Opin. Clin. Nutr. Metab. Care 6, 217 (2003) (Review)
Glutamate synthase: a fascinating pathway from L-glutamine to L-glutamate: R.H. van den Heuvel, et al.; Cell Mol. Life Sci. 61, 669 (2004) (Review)
Supplementation with L-glutamine prevents tumor growth and cancer-induced cachexia as well as restores cell proliferation of intestinal mucosa of Walker-256 tumor-bearing rats: H.A. Martins, et al.; Amino Acids 48, 2773 (2016)
Glutamine Links Obesity to Inflammation in Human White Adipose Tissue: P. Petrus, et al.; Cell Metab. 31, 375 (2020)

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