Basic information
- CAS
56-85-9- Standard SMILES
NC(=O)CC[C@H]([NH3+])C(=O)[O-]- InChIKey
ZDXPYRJPNDTMRX-VKHMYHEASA-N- Molecular formula
- C5H10N2O3
- Average molar mass
- 146.14 g/mol
- Monoisotopic mass
- 146.06914219
Overview
L-glutamine zwitterion is an amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-glutamine; major species at pH 7.3. It has a role as a metabolite. It is an amino-acid zwitterion and a polar amino acid zwitterion. It is a tautomer of a L-glutamine.
Names & identifiers
- Preferred name
- (2S)-5-amino-2-ammonio-5-oxopentanoate
- IUPAC
- (2S)-5-amino-2-azaniumyl-5-oxopentanoate
- English name
- L-Glutamine
- Molecular formula
- C5H10N2O3
- Molecular weight
- 146.14
Names & synonyms
(2S)-5-amino-2-ammonio-5-oxopentanoateL-glnglumL-glutamine zwitterionCHEBI:58359GLUTAMINEGLNH-GLN-OHL-GlutaminL-Gln-OHFEMA 3684H-L-GLN-OH
Show more names
LEVOGLUTAMIDEL-GLUTAMIC ACID AMIDE
Database identifiers
- CAS
56-85-9- PubChem CID
- 6992086
- ChEBI
CHEBI:58359- Nikkaji
- J2.220.007K
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 140
Experimental & physicochemical properties
LogP-3.64
Solubility41.3 mg/mL
Melting Point185 °C
Physical DescriptionSolid
Dissociation Constants2.17
Physicochemical properties
- Melting point
- 185 °C · decomposes around 185°C
- alpha
- 32.25 · 32.25 º (c=10, 2 N HCl)
- Boiling point
- 265.74 °C · 265.74°C (rough estimate)
- bulk density
- 640 kg/m3 · 640kg/m3
- Density
- 1.47 g/cm · 1.47 g/cm 3 at 20 °C
- refractive index
- 6.8 ° · 6.8 ° (C=4, H2O)
- FEMA
- 3684 · 3684 | L-GLUTAMINE
- FLAVIS Number
- 17.007 · 17.007 | Glutamine
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- MA2275100
- hs_code
- 29241900
- Toxicity
- LD50 orally in Rabbit: 7500 mg/kg
- risk_code
- 36-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-24/25-36/37/39-27
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
- Hazardous Substances Data
- 56-85-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Pharmacodynamics
Like other amino acids, glutamine is biochemically important as a constituent of proteins. Glutamine is also crucial in nitrogen metabolism. Ammonia (formed by nitrogen fixation) is assimilated into organic compounds by converting glutamic acid to glutamine. The enzyme which accomplishes this is called glutamine synthetase. Glutamine can then be used as a nitrogen donor in the biosynthesis of many compounds, including other amino acids, purines, and pyrimidines. L-glutamine improves nicotinamide adenine dinucleotide (NAD) redox potential.
Mechanism of Action
Supplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed. The exact mechanism of L-glutamine's effect on NAD redox potential is unknown but is thought to involve increased amounts of reduced glutathione made available by glutamine supplementation. This improvement in redox potential reduces the amount of oxidative damage which sickle red blood cells are more susceptible to. The reduction in cellular damage is thought to reduce chronic hemolysis and vaso-occlusive events.
Related reactions
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Compound notes
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