2.0 2012-05-31 14:51:22 -0600 2015-06-03 17:20:19 -0600 ECMDB20574 M2MDB001377 L-Ala-gamma-D-Glu L-ala-gamma-D-glu is a member of the chemical class known as Hybrid Peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta). UDPMurNAc-L-Ala-gamma-D-Glu-X-D-Ala-DAla (X = L-Lys or m-DAP) is the cytoplasmic precursor for the lipid-linked cycle of bacterial peptidoglycan biosynthesis, consisting of at least four enzymatic reactions, which are targets for antibacterial agents. (PMID 17216029) L-Ala-&gamma;-D-Glu L-Ala-g-D-glu L-Ala-γ-D-glu L-Alanine-D-glutamate L-Alanine-D-glutamic acid C8H13N2O5 217.1992 217.082446536 (4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxybutanoate (4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxybutanoate [H][C@@](C)(N)C(O)=N[C@]([H])(CCC([O-])=O)C(O)=O InChI=1S/C8H14N2O5/c1-4(9)7(13)10-5(8(14)15)2-3-6(11)12/h4-5H,2-3,9H2,1H3,(H,10,13)(H,11,12)(H,14,15)/p-1/t4-,5+/m0/s1 VYZAGTDAHUIRQA-CRCLSJGQSA-M Cytosol Extra-organism Periplasm logp -3.07 ALOGPS logs -1.30 ALOGPS solubility 1.17e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 3.58 ChemAxon pka_strongest_basic 9.57 ChemAxon iupac (4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxybutanoate ChemAxon average_mass 217.1992 ChemAxon mono_mass 217.082446536 ChemAxon smiles [H][C@@](C)(N)C(O)=N[C@]([H])(CCC([O-])=O)C(O)=O ChemAxon formula C8H13N2O5 ChemAxon inchi InChI=1S/C8H14N2O5/c1-4(9)7(13)10-5(8(14)15)2-3-6(11)12/h4-5H,2-3,9H2,1H3,(H,10,13)(H,11,12)(H,14,15)/p-1/t4-,5+/m0/s1 ChemAxon inchikey VYZAGTDAHUIRQA-CRCLSJGQSA-M ChemAxon polar_surface_area 136.04 ChemAxon refractivity 59.94 ChemAxon polarizability 20.21 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge -1 ChemAxon Specdb::NmrOneD 279858 Specdb::NmrOneD 279859 Specdb::NmrOneD 279860 Specdb::NmrOneD 279861 Specdb::NmrOneD 279862 Specdb::NmrOneD 279863 Specdb::NmrOneD 279864 Specdb::NmrOneD 279865 Specdb::NmrOneD 279866 Specdb::NmrOneD 279867 Specdb::NmrOneD 279868 Specdb::NmrOneD 279869 Specdb::NmrOneD 279870 Specdb::NmrOneD 279871 Specdb::NmrOneD 279872 Specdb::NmrOneD 279873 Specdb::NmrOneD 279874 Specdb::NmrOneD 279875 Specdb::NmrOneD 279876 Specdb::NmrOneD 279877 Specdb::MsMs 25385 Specdb::MsMs 25386 Specdb::MsMs 25387 Specdb::MsMs 31943 Specdb::MsMs 31944 Specdb::MsMs 31945 25203551 19260405 CPD0-2190 Keseler, 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. 21097882 van 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. 17765195 Schouten, J. A., Bagga, S., Lloyd, A. J., de Pascale, G., Dowson, C. G., Roper, D. I., Bugg, T. D. (2006). "Fluorescent reagents for in vitro studies of lipid-linked steps of bacterial peptidoglycan biosynthesis: derivatives of UDPMurNAc-pentapeptide containing d-cysteine at position 4 or 5." Mol Biosyst 2:484-491. 17216029 L-Ala-D/L-Glu epimerase P51981 AEEP_ECOLI ycjG http://ecmdb.ca/proteins/P51981.xml Protein mpaA P0ACV6 MPAA_ECOLI mpaA http://ecmdb.ca/proteins/P0ACV6.xml L-Ala-gamma-D-Glu-Dap + Water > L-Ala-gamma-D-Glu + <i>meso</i>-diaminopimelate RXN0-961 L-Ala-gamma-D-Glu L-Alanyl-L-Glutamate RXN0-5228