1.0 2011-09-21 00:27:57 UTC 2015-07-21 06:57:38 UTC FDB023317 Poly-gamma-D-glutamate Poly-gamma-D-glutamate or PGA is an intermediate in D-Glutamine and D-glutamate metabolism. It is a polymer of D-glutamate residues. It is produced by bacteria, a number of which are part of the normal human microflora. In particular, Staph. epidermidis secretes poly-gamma-glutamate (PGA) to facilitate growth and ensure its survival inside the human host. PGA protects the pathogen from innate host defenses during infection. S. epidermidis is the only human pathogen known to produce PGA other than Bacillus anthracis, but several differences exist in how the two pathogens use PGA to their advantage. What is shown in the attached diagram is a tetramer of poly-gamma-glutamate. PGA is currently used as an antigen for vaccine production against Anthrax. Poly-gamma-D-glutamate is produced from L-Glutamate via a multi-step reaction. [HMDB] PGA Poly-g-D-glutamate Poly-g-D-glutamic acid Poly-gamma-D-glutamate Poly-gamma-D-glutamic acid Poly-gamma-delta-glutamate Poly-gamma-delta-glutamic acid Poly-gamma-glutamate Poly-gamma-glutamic acid C20H30N4O12 518.4718 518.186022444 (2R)-2-[(4R)-4-[(4R)-4-[(4R)-4-amino-4-carboxybutanamido]-4-carboxybutanamido]-4-carboxybutanamido]-5-oxopentanoic acid (2R)-2-[(4R)-4-[(4R)-4-[(4R)-4-amino-4-carboxybutanamido]-4-carboxybutanamido]-4-carboxybutanamido]-5-oxopentanoic acid N[C@H](CCC(=O)N[C@H](CCC(=O)N[C@H](CCC(=O)N[C@H](CCC=O)C(O)=O)C(O)=O)C(O)=O)C(O)=O InChI=1S/C20H30N4O12/c21-10(17(29)30)3-6-14(26)23-12(19(33)34)5-8-16(28)24-13(20(35)36)4-7-15(27)22-11(18(31)32)2-1-9-25/h9-13H,1-8,21H2,(H,22,27)(H,23,26)(H,24,28)(H,29,30)(H,31,32)(H,33,34)(H,35,36)/t10-,11-,12-,13-/m1/s1 LJVWRHJDEMCHNS-FDYHWXHSSA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Alpha-hydrogen aldehydes Amino acids Carboxylic acids D-alpha-amino acids Gamma-glutamyl amino acids Glutamine and derivatives Hydrocarbon derivatives Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Tetracarboxylic acids and derivatives Aldehyde Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid or derivatives Alpha-hydrogen aldehyde Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid D-alpha-amino acid Fatty acyl Fatty amide Gamma-glutamyl alpha-amino acid Glutamine or derivatives Hydrocarbon derivative N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide Tetracarboxylic acid or derivatives Solid logp -2.56 ALOGPS logs -2.71 ALOGPS solubility 1.01e+00 g/l ALOGPS logp -6.2 ChemAxon pka_strongest_acidic 1.91 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2R)-2-[(4R)-4-[(4R)-4-[(4R)-4-amino-4-carboxybutanamido]-4-carboxybutanamido]-4-carboxybutanamido]-5-oxopentanoic acid ChemAxon average_mass 518.4718 ChemAxon mono_mass 518.186022444 ChemAxon smiles N[C@H](CCC(=O)N[C@H](CCC(=O)N[C@H](CCC(=O)N[C@H](CCC=O)C(O)=O)C(O)=O)C(O)=O)C(O)=O ChemAxon formula C20H30N4O12 ChemAxon inchi InChI=1S/C20H30N4O12/c21-10(17(29)30)3-6-14(26)23-12(19(33)34)5-8-16(28)24-13(20(35)36)4-7-15(27)22-11(18(31)32)2-1-9-25/h9-13H,1-8,21H2,(H,22,27)(H,23,26)(H,24,28)(H,29,30)(H,31,32)(H,33,34)(H,35,36)/t10-,11-,12-,13-/m1/s1 ChemAxon inchikey LJVWRHJDEMCHNS-FDYHWXHSSA-N ChemAxon polar_surface_area 279.59 ChemAxon refractivity 114.63 ChemAxon polarizability 48.89 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10846 Specdb::CMs 38720 Specdb::MsMs 289885 Specdb::MsMs 289886 Specdb::MsMs 289887 Specdb::MsMs 329443 Specdb::MsMs 329444 Specdb::MsMs 329445 Specdb::MsMs 2787943 Specdb::MsMs 2787944 Specdb::MsMs 2787945 Specdb::MsMs 2918039 Specdb::MsMs 2918040 Specdb::MsMs 2918041 Specdb::NmrOneD 149820 Specdb::NmrOneD 149821 Specdb::NmrOneD 149822 Specdb::NmrOneD 149823 Specdb::NmrOneD 149824 Specdb::NmrOneD 149825 Specdb::NmrOneD 149826 Specdb::NmrOneD 149827 Specdb::NmrOneD 149828 Specdb::NmrOneD 149829 Specdb::NmrOneD 149830 Specdb::NmrOneD 149831 Specdb::NmrOneD 149832 Specdb::NmrOneD 149833 Specdb::NmrOneD 149834 Specdb::NmrOneD 149835 Specdb::NmrOneD 149836 Specdb::NmrOneD 149837 Specdb::NmrOneD 149838 Specdb::NmrOneD 149839 HMDB04135 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823