2.02012-05-31 13:59:03 -06002015-09-13 12:56:13 -0600ECMDB03423M2MDB000500D-GlutamineD-glutamine is a non-essential amino acid and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen and is an important energy source for many cells.D-2-AminoglutaramateD-2-Aminoglutaramic acidGlutamideNutrestoreC5H10N2O3146.1445146.069142196(2R)-2-amino-4-carbamoylbutanoic acidD-glutamine5959-95-5N[C@H](CCC(N)=O)C(O)=OInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1ZDXPYRJPNDTMRX-GSVOUGTGSA-NSolidCytoplasmPeriplasmlogp-3.32logs-0.17solubility9.78e+01 g/llogp-4pka_strongest_acidic2.15pka_strongest_basic9.31iupac(2R)-2-amino-4-carbamoylbutanoic acidaverage_mass146.1445mono_mass146.069142196smilesN[C@H](CCC(N)=O)C(O)=OformulaC5H10N2O3inchiInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1inchikeyZDXPYRJPNDTMRX-GSVOUGTGSA-Npolar_surface_area106.41refractivity33.11polarizability13.59rotatable_bond_count4acceptor_count4donor_count3physiological_charge0formal_charge0D-Glutamine and D-glutamate metabolismL-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine.
L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter.
L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase.
D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis
UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase.
PW000769ec00471MetabolicSpecdb::CMs845Specdb::CMs3334Specdb::CMs30098Specdb::CMs30595Specdb::CMs38597Specdb::CMs166374Specdb::NmrOneD1968Specdb::NmrOneD21822Specdb::NmrOneD21823Specdb::NmrOneD21824Specdb::NmrOneD21825Specdb::NmrOneD21826Specdb::NmrOneD21827Specdb::NmrOneD21828Specdb::NmrOneD21829Specdb::NmrOneD21830Specdb::NmrOneD21831Specdb::NmrOneD21832Specdb::NmrOneD21833Specdb::NmrOneD21834Specdb::NmrOneD21835Specdb::NmrOneD21836Specdb::NmrOneD21837Specdb::NmrOneD21838Specdb::NmrOneD21839Specdb::NmrOneD21840Specdb::NmrOneD21841Specdb::NmrOneD166612Specdb::NmrOneD166613Specdb::MsMs2301Specdb::MsMs2302Specdb::MsMs2303Specdb::MsMs5937Specdb::MsMs5938Specdb::MsMs5939Specdb::MsMs5940Specdb::MsMs5941Specdb::MsMs179943Specdb::MsMs179944Specdb::MsMs179945Specdb::MsMs182277Specdb::MsMs182278Specdb::MsMs182279Specdb::MsMs446171Specdb::MsMs446172Specdb::MsMs446173Specdb::MsMs446174Specdb::MsMs446175Specdb::MsMs2319554Specdb::MsMs2319555Specdb::MsMs2319556Specdb::MsMs2619851Specdb::MsMs2619852Specdb::MsMs2619853Specdb::NmrTwoD1903HMDB03423145815128633C0081917061GLUTAMIDEDGNKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Thorsen G, Bergquist J: Chiral separation of amino acids in biological fluids by micellar electrokinetic chromatography with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2000 Aug 18;745(2):389-97.11043757Qian, Shao-Song; Wu, Xiao-Yan; Li, Jia-You; Liu, Yi; Chen, Ran; Jiao, Qing-Cai. Preparation of D-glutamine from glutamic acid. Youji Huaxue (2006), 26(4), 514-517.http://hmdb.ca/system/metabolites/msds/000/003/004/original/HMDB03423.pdf?1358462966Glutaminase 2P0A6W0GLSA2_ECOLIglsA2http://ecmdb.ca/proteins/P0A6W0.xmlGlutaminase 1P77454GLSA1_ECOLIglsA1http://ecmdb.ca/proteins/P77454.xmlGlutamine transport system permease protein glnPP0AEQ6GLNP_ECOLIglnPhttp://ecmdb.ca/proteins/P0AEQ6.xmlUncharacterized amino-acid ABC transporter ATP-binding protein yecCP37774YECC_ECOLIyecChttp://ecmdb.ca/proteins/P37774.xmlInner membrane amino-acid ABC transporter permease protein yecSP0AFT2YECS_ECOLIyecShttp://ecmdb.ca/proteins/P0AFT2.xmlGlutamine transport system permease protein glnPP0AEQ6GLNP_ECOLIglnPhttp://ecmdb.ca/proteins/P0AEQ6.xmlD-Glutamine + Water <> D-Glutamic acid + AmmoniaR01579D-Glutamine + Water > D-Glutamic acid + AmmoniaPW_R002516D-Glutamine + Water <> D-Glutamic acid + Ammonia