2.0 2012-05-31 14:51:25 -0600 2015-06-03 17:20:19 -0600 ECMDB20575 M2MDB001378 L-Ala-gamma-D-Glu-Dap L-ala-gamma-D-glu-DAP 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). L-alanyl-gamma-D-glutamyl-meso-diaminopimelate is related to MppA. MppA is a periplasmic binding protein in Escherichia coli essential for uptake of the cell wall murein tripeptide L-alanyl-gamma-D-glutamyl-meso-diaminopimelate. (PMID 10438753) L-Ala-&gamma;-D-Glu-diaminopimelate L-Ala-&gamma;-D-glu-diaminopimelic acid L-Ala-g-D-glu-dap L-Ala-g-D-glu-diaminopimelate L-Ala-g-D-glu-diaminopimelic acid L-Ala-gamma-D-Glu-diaminopimelate L-Ala-gamma-D-Glu-diaminopimelic acid L-Ala-γ-D-glu-dap L-Ala-γ-D-glu-diaminopimelate L-Ala-γ-D-glu-diaminopimelic acid L-alanyl-&gamma;-D-glutamyl-<i>meso</i>-diaminopimelate L-Alanyl-&gamma;-D-glutamyl-meso-diaminopimelate L-Alanyl-&gamma;-D-glutamyl-meso-diaminopimelic acid L-Alanyl-g-D-glutamyl-meso-diaminopimelate L-Alanyl-g-D-glutamyl-meso-diaminopimelic acid L-Alanyl-gamma-D-glutamyl-meso-diaminopimelate L-Alanyl-gamma-D-glutamyl-meso-diaminopimelic acid L-Alanyl-γ-D-glutamyl-meso-diaminopimelate L-Alanyl-γ-D-glutamyl-meso-diaminopimelic acid C13H19N5O4 309.3211 309.143704121 4-[(2-amino-1-hydroxypropylidene)amino]-4-[(6-imino-1,6-dihydropyridin-2-yl)-C-hydroxycarbonimidoyl]butanoic acid 4-[(2-amino-1-hydroxypropylidene)amino]-4-[(6-imino-1H-pyridin-2-yl)-C-hydroxycarbonimidoyl]butanoic acid CC(N)C(O)=NC(CCC(O)=O)C(O)=NC1=CC=CC(=N)N1 InChI=1S/C13H19N5O4/c1-7(14)12(21)16-8(5-6-11(19)20)13(22)18-10-4-2-3-9(15)17-10/h2-4,7-8H,5-6,14H2,1H3,(H,16,21)(H,19,20)(H3,15,17,18,22) IBYVCSBRMYGDRR-UHFFFAOYSA-N Cytoplasm Periplasm logp -2.29 ALOGPS logs -3.36 ALOGPS solubility 1.34e-01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic -0.17 ChemAxon pka_strongest_basic 18.93 ChemAxon iupac 4-[(2-amino-1-hydroxypropylidene)amino]-4-[(6-imino-1,6-dihydropyridin-2-yl)-C-hydroxycarbonimidoyl]butanoic acid ChemAxon average_mass 309.3211 ChemAxon mono_mass 309.143704121 ChemAxon smiles CC(N)C(O)=NC(CCC(O)=O)C(O)=NC1=CC=CC(=N)N1 ChemAxon formula C13H19N5O4 ChemAxon inchi InChI=1S/C13H19N5O4/c1-7(14)12(21)16-8(5-6-11(19)20)13(22)18-10-4-2-3-9(15)17-10/h2-4,7-8H,5-6,14H2,1H3,(H,16,21)(H,19,20)(H3,15,17,18,22) ChemAxon inchikey IBYVCSBRMYGDRR-UHFFFAOYSA-N ChemAxon polar_surface_area 164.38 ChemAxon refractivity 99.88 ChemAxon polarizability 31.29 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1083935 Specdb::EiMs 4614 Specdb::NmrOneD 278938 Specdb::NmrOneD 278939 Specdb::NmrOneD 278940 Specdb::NmrOneD 278941 Specdb::NmrOneD 278942 Specdb::NmrOneD 278943 Specdb::NmrOneD 278944 Specdb::NmrOneD 278945 Specdb::NmrOneD 278946 Specdb::NmrOneD 278947 Specdb::NmrOneD 278948 Specdb::NmrOneD 278949 Specdb::NmrOneD 278950 Specdb::NmrOneD 278951 Specdb::NmrOneD 278952 Specdb::NmrOneD 278953 Specdb::NmrOneD 278954 Specdb::NmrOneD 278955 Specdb::NmrOneD 278956 Specdb::NmrOneD 278957 Specdb::MsMs 24419 Specdb::MsMs 24420 Specdb::MsMs 24421 Specdb::MsMs 30977 Specdb::MsMs 30978 Specdb::MsMs 30979 656477 570864 L-ALA-GAMMA-D-GLU-DAP 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 Li, H., Park, J. T. (1999). "The periplasmic murein peptide-binding protein MppA is a negative regulator of multiple antibiotic resistance in Escherichia coli." J Bacteriol 181:4842-4847. 10438753 Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.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-DAP-D-Ala + Water L-Ala-gamma-D-Glu-Dap + D-Alanine RXN0-5227