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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 12:33:38 UTC
Update Date2021-09-14 15:20:00 UTC
HMDB IDHMDB0004135
Secondary Accession Numbers
  • HMDB04135
Metabolite Identification
Common NamePoly-g-D-glutamate
DescriptionPoly-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.
Structure
Thumb
Synonyms
ValueSource
Poly-g-D-glutamic acidGenerator
PGAHMDB
Poly-gamma-D-glutamateHMDB
Poly-gamma-D-glutamic acidHMDB, Generator
Poly-gamma-delta-glutamateHMDB
Poly-gamma-delta-glutamic acidHMDB
Poly-gamma-glutamateHMDB
Poly-gamma-glutamic acidHMDB
(2R)-2-{[(4R)-4-{[(4R)-4-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}-5-oxopentanoateGenerator, HMDB
Poly-g-D-glutamateGenerator
Poly-γ-D-glutamateGenerator
Poly-γ-D-glutamic acidGenerator
Chemical FormulaC20H30N4O12
Average Molecular Weight518.4718
Monoisotopic Molecular Weight518.186022444
IUPAC Name(2R)-2-[(4R)-4-[(4R)-4-[(4R)-4-amino-4-carboxybutanamido]-4-carboxybutanamido]-4-carboxybutanamido]-5-oxopentanoic acid
Traditional Name(2R)-2-[(4R)-4-[(4R)-4-[(4R)-4-amino-4-carboxybutanamido]-4-carboxybutanamido]-4-carboxybutanamido]-5-oxopentanoic acid
CAS Registry NumberNot Available
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
InChI Identifier
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
InChI KeyLJVWRHJDEMCHNS-FDYHWXHSSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid
  • Organic oxide
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Primary amine
  • Aldehyde
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-5.016Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023317
KNApSAcK IDNot Available
Chemspider ID30776562
KEGG Compound IDC05723
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477778
PDB IDNot Available
ChEBI ID169453
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available