Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000491
Name: D-Glutamic acid
Description:D-glutamate is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid is found naturally primarily in the cell walls of certain bacteria - including Pseudomonas aeruginosa. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date.
  • (2R)-2-aminopentanedioate
  • (2R)-2-aminopentanedioic acid
  • (R)-2-aminopentanedioate
  • (R)-2-aminopentanedioic acid
  • D-2-Aminoglutarate
  • D-2-Aminoglutaric acid
  • D-2-Aminopentanedioate
  • D-2-Aminopentanedioic acid
  • D-Glu
  • D-Glutamate
  • D-Glutamic acid
  • D-Glutaminate
  • D-Glutaminic acid
  • D-Glutaminsaeure
  • Delta-2-Aminoglutarate
  • Delta-2-Aminoglutaric acid
  • Delta-2-Aminopentanedioate
  • Delta-2-Aminopentanedioic acid
  • Delta-Glutamate
  • Delta-Glutamic acid
  • Delta-Glutaminate
  • Delta-Glutaminic acid
  • Delta-Glutaminsaeure
  • DGL
  • Glutamate
  • Glutamate D-form
  • Glutamic acid
  • Glutamic acid D-form
  • Lopac-G-2128
  • Lopac-gamma-2128
  • Lopac-γ-2128
  • R-(-)-Glutamate
  • R-(-)-Glutamic acid
  • Tocris-0217
  • δ-2-Aminoglutarate
  • δ-2-Aminoglutaric acid
  • δ-2-Aminopentanedioate
  • δ-2-Aminopentanedioic acid
  • δ-Glutamate
  • δ-Glutamic acid
  • δ-Glutaminate
  • δ-Glutaminic acid
  • δ-Glutaminsaeure
Chemical Formula: C5H9NO4
Average Molecular Weight: 147.1293
Monoisotopic Molecular Weight: 147.053157781
CAS number: 6893-26-1
IUPAC Name:(2R)-2-aminopentanedioic acid
Traditional IUPAC Name: D-glutamic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent D-alpha-amino acids
Alternative Parents
  • D-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 201 °C
Experimental Properties:
Water Solubility:8.88 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
Water Solubility80.6 mg/mLALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.29 m3·mol-1ChemAxon
Polarizability13.19 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-58248bb2a0c7ddc905cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-9600000000-076b628a6858a60a475fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bd3823a5fab8a2d9b62cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-11233b5887638266e512View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-4900000000-1e8ea62e3fbd8467396fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-6c956e122b59de69a472View in MoNA
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  • Emi M, Wilson DE, Iverius PH, Wu L, Hata A, Hegele R, Williams RR, Lalouel JM: Missense mutation (Gly----Glu188) of human lipoprotein lipase imparting functional deficiency. J Biol Chem. 1990 Apr 5;265(10):5910-6. Pubmed: 1969408
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  • Kanehisa, 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • Luo J, Kaplitt MG, Fitzsimons HL, Zuzga DS, Liu Y, Oshinsky ML, During MJ: Subthalamic GAD gene therapy in a Parkinson's disease rat model. Science. 2002 Oct 11;298(5592):425-9. Pubmed: 12376704
  • Maechler P, Gjinovci A, Wollheim CB: Implication of glutamate in the kinetics of insulin secretion in rat and mouse perfused pancreas. Diabetes. 2002 Feb;51 Suppl 1:S99-102. Pubmed: 11815466
  • Majid SM, Liss AS, You M, Bose HR: The suppression of SH3BGRL is important for v-Rel-mediated transformation. Oncogene. 2006 Feb 2;25(5):756-68. Pubmed: 16186799
  • Mally MI, Cirulli V, Hayek A, Otonkoski T: ICA69 is expressed equally in the human endocrine and exocrine pancreas. Diabetologia. 1996 Apr;39(4):474-80. Pubmed: 8777998
  • Meyer W, Poehling HM, Neurand K: Intraepidermal distribution of free amino acids in porcine skin. J Dermatol Sci. 1991 Sep;2(5):383-92. Pubmed: 1742249
  • Nagai A, Suzuki Y, Baek SY, Lee KS, Lee MC, McLarnon JG, Kim SU: Generation and characterization of human hybrid neurons produced between embryonic CNS neurons and neuroblastoma cells. Neurobiol Dis. 2002 Oct;11(1):184-98. Pubmed: 12460557
  • Nielsen C, Hansen D, Husby S, Jacobsen BB, Lillevang ST: No allelic variation in genes with high gliadin homology in patients with celiac disease and type 1 diabetes. Immunogenetics. 2004 Aug;56(5):375-8. Epub 2004 Aug 7. Pubmed: 15309343
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  • Roll U, Scheeser J, Standl E, Ziegler AG: Alterations of lymphocyte subsets in children of diabetic mothers. Diabetologia. 1994 Nov;37(11):1132-41. Pubmed: 7867885
  • Wang M, Meng Z, Fu J: Synthesis and biodistribution of six novel 99mTc complexes of 2-hydroxybenzaldehyde-amino acid Schiff bases. Appl Radiat Isot. 2006 Feb;64(2):235-40. Pubmed: 16309915
  • Winder, 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. Pubmed: 18331064
Synthesis Reference: Ozaki, Akio; Yagasaki, Makoto; Takada, Hideyoshi; Hashimoto, Yukio. Manufacture of D-glutamic acid with Lactobacillus. Jpn. Kokai Tokkyo Koho (1990), 4 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID23327
Kegg IDC00217
ChemSpider ID21814
Ligand ExpoFGA


General function:
Involved in glutaminase activity
Specific function:
L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:
Locus Tag:
Molecular weight:
33 kDa
L-glutamine + H(2)O = L-glutamate + NH(3).
General function:
Involved in ATP binding
Specific function:
Cell wall formation. Catalyzes the addition of glutamate to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanine (UMA)
Gene Name:
Locus Tag:
Molecular weight:
48.1 kDa
ATP + UDP-N-acetylmuramoyl-L-alanine + glutamate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate.
General function:
Involved in racemase and epimerase activity, acting on amino acids and derivatives
Specific function:
Provides the (R)-glutamate required for cell wall biosynthesis
Gene Name:
Locus Tag:
Molecular weight:
28.3 kDa
L-glutamate = D-glutamate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
27.6 kDa
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
24.6 kDa


General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
Locus Tag:
Molecular weight:
28.4 kDa
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
27.6 kDa
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
24.6 kDa
General function:
Involved in glutamate:sodium symporter activity
Specific function:
Catalyzes the sodium-dependent uptake of extracellular glutamate
Gene Name:
Locus Tag:
Molecular weight:
42.8 kDa