Compound: DL-Glutamine
SMILES: O=C(O)C(N)CCC(=O)N
InChIKey: ZDXPYRJPNDTMRX-UHFFFAOYSA-N
Synonyms: DL-Glutamine, 6899-04-3, 585-21-7, Glutamine, DL-, NSC-97925, 5L555N1902, DTXSID1044304, Glutamine DL-, RefChem:1083901, DTXCID9024304, 5-amino-2-azaniumyl-5-oxopentanoate, 230-006-0, H-DL-Gln-OH, 2-amino-4-carbamoylbutanoic acid, MFCD00065103, .gamma.-Glutamine, Pomalidomide Impurity 12, glutamin, (+/-)-Glutamine;DL-Gl, d(-)-glutamine, Glutamine DL-form, SR-01000075451, L-Glutamic acid .gamma.-amide, Hgln, DL Glutamine, 2-Amino-4-carbamoylbutyric acid, 2,5-diamino-5-oxo-pentanoic acid, S(+)-Glutamine, (+-)-Glutamine, Glutaminsaeure-5-amid, ()-Glutamine;DL-Gl, DL-GLN, glutamic acid gamma-amide, SCHEMBL7452, (+/-)-GLUTAMINE, NCIOpen2_001762, D(-)-Glutamic acid-5-amide, SCHEMBL1118712, SCHEMBL2302387, GLUTAMINE DL-FORM [MI], 2-amino-4-carbamoyl-butyric acid, UNII-5L555N1902, EIA45148, HY-B1346, NSC97925, EINECS 230-006-0, L-Glutamine, from non-animal origin, EBC-44056, NSC 97925, s3963, STL281858, AKOS000120990, AKOS016368274, CCG-266175, CS-4898, FG39660, L-Glutamine USP from non-animal origin, AC-24108, DS-14402, Pentanoic acid,5-diamino-5-oxo-, (S)-, SY030495, AI3-32686, DB-053215, DB-053421, G0062, NS00006419, NS00096392, EN300-21443, C00303, F093746, L000914, SR-01000075451-1, SR-01000075451-4, SR-01000075451-5, Q27103623, Z104497332, D3B73117-6905-4CF4-AC3E-565B11432FFA
Theoretical properties:
molecular_formula: C5H10N2O3
molecular_weight: 146.14 g/mol
exact_mass: 146.06914219 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 10
topological_polar_surface_area: 106 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Glutamine is an alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4. It has a role as a fundamental metabolite. It is a polar amino acid and an alpha-amino acid. It contains a 3-amino-3-oxopropyl group. It is a conjugate base of a glutaminium. It is a conjugate acid of a glutaminate.
chebi: An α-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.
wikipedia: Glutamine synthetase (GS) (EC 6.3.1.2) is an enzyme that catalyzes the condensation of glutamate and ammonia to form glutamine:
Glutamate + ATP + NH3 → Glutamine + ADP + phosphate 

Glutamine synthetase uses ammonia produced by nitrate reduction, amino acid degradation, and photorespiration. The amide group of glutamate is a nitrogen source for the synthesis of glutamine pathway metabolites.
Other reactions may take place via GS. Competition between ammonium ion and water, their binding affinities, and the concentration of ammonium ion, influences glutamine synthesis and glutamine hydrolysis. Glutamine is formed if an ammonium ion attacks the acyl-phosphate intermediate, while glutamate is remade if water attacks the intermediate.  Ammonium ion binds more strongly than water to GS due to electrostatic forces between a cation and a negatively charged pocket. Another possible reaction is upon NH2OH binding to GS, rather than NH4+, yields γ-glutamylhydroxamate.