Record Information
Version2.0
Creation Date2012-05-31 13:58:34 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB03339
Identification
Name:D-Glutamic acid
DescriptionD-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 E. coli. 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.
Structure
Thumb
Synonyms:
  • (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
Weight:Average: 147.1293
Monoisotopic: 147.053157781
InChI Key:WHUUTDBJXJRKMK-GSVOUGTGSA-N
InChI:InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1
CAS number:6893-26-1
IUPAC Name:(2R)-2-aminopentanedioic acid
Traditional IUPAC Name:D-glutamic acid
SMILES:N[C@H](CCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:201 °C
Experimental Properties:
PropertyValueSource
Water Solubility:8.88 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility80.6 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.29 m³·mol⁻¹ChemAxon
Polarizability13.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
D-Glutamic acid <> L-Glutamate
L-Glutamate <> D-Glutamic acid
D-Glutamine + Water <> D-Glutamic acid + Ammonia
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanine + D-Glutamic acid <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
Pyridoxamine 5'-phosphate + Oxoglutaric acid <> Pyridoxal 5'-phosphate + D-Glutamic acid
D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Phosphate + ADP
L-Glutamate > D-Glutamic acid
D-Glutamine + Water > D-Glutamic acid + Ammonia
L-Glutamic acid + L-Glutamate <> D-Glutamic acid
UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate + D-Glutamic acid > Adenosine diphosphate + Phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
UDP-N-Acetylmuramyl-L-Ala + Adenosine triphosphate + D-Glutamic acid > UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + ADP + Phosphate
D-Glutamine + Water <> D-Glutamic acid + Ammonia
Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
D-Glutamic acid <> L-Glutamate
Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
D-Glutamic acid <> L-Glutamate
SMPDB Pathways:
D-Glutamine and D-glutamate metabolismPW000769 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9x-9300000000-a43e0122a45b9abf09d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9240000000-53c8c708191dfcd550d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ad4a2989e599a67182c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-c449cfd2231fe941d44fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-f71458032a132069f94fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-7900000000-810570c8cfcea8da64f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5167570d11d77fd541eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-c7d42b011a328bb7991dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-9fd882f84339f600b5ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-407a30a35de9c1cceb3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8610ea89d52ef116caf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-331b7ed6ea33880c306eView in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-4900000000-c467fa409affedc9ab85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-ddda6500978ea1670dcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c6639c8639f077b57a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-4900000000-503f6a47bc72662de09cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-3900000000-ec06b29308ff068bf7a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e06c31345e8a86e71de1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62. Pubmed: 7914846
  • Bill JR, Mack DG, Falta MT, Maier LA, Sullivan AK, Joslin FG, Martin AK, Freed BM, Kotzin BL, Fontenot AP: Beryllium presentation to CD4+ T cells is dependent on a single amino acid residue of the MHC class II beta-chain. J Immunol. 2005 Nov 15;175(10):7029-37. Pubmed: 16272364
  • Canal N, Nemni R: Autoimmunity and diabetic neuropathy. Clin Neurosci. 1997;4(6):371-3. Pubmed: 9358982
  • Cuervo JH, Rodriguez B, Houghten RA: The Magainins: sequence factors relevant to increased antimicrobial activity and decreased hemolytic activity. Pept Res. 1988 Nov-Dec;1(2):81-6. Pubmed: 2980783
  • Danke NA, Koelle DM, Yee C, Beheray S, Kwok WW: Autoreactive T cells in healthy individuals. J Immunol. 2004 May 15;172(10):5967-72. Pubmed: 15128778
  • 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
  • Guariso G, Brotto F, Basso D, Alaggio R, Betterle C: Organ-specific autoantibodies in children with Helicobacter pylori infection. Helicobacter. 2004 Dec;9(6):622-8. Pubmed: 15610075
  • 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
  • Persson H, Pelto-Huikko M, Metsis M, Soder O, Brene S, Skog S, Hokfelt T, Ritzen EM: Expression of the neurotransmitter-synthesizing enzyme glutamic acid decarboxylase in male germ cells. Mol Cell Biol. 1990 Sep;10(9):4701-11. Pubmed: 1697032
  • Raj D, Langford M, Krueger S, Shelton M, Welbourne T: Regulatory responses to an oral D-glutamate load: formation of D-pyrrolidone carboxylic acid in humans. Am J Physiol Endocrinol Metab. 2001 Feb;280(2):E214-20. Pubmed: 11158923
  • 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:
ResourceLink
CHEBI ID15966
HMDB IDHMDB03339
Pubchem Compound ID23327
Kegg IDC00217
ChemSpider ID21814
WikipediaDGL
BioCyc IDD-GLT
EcoCyc IDD-GLT
Ligand ExpoFGA

Enzymes

General function:
Involved in glutaminase activity
Specific function:
L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:
glsA2
Uniprot ID:
P0A6W0
Molecular weight:
33515
Reactions
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:
murD
Uniprot ID:
P14900
Molecular weight:
46973
Reactions
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:
murI
Uniprot ID:
P22634
Molecular weight:
31002
Reactions
L-glutamate = D-glutamate.
General function:
Involved in glutaminase activity
Specific function:
L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:
glsA1
Uniprot ID:
P77454
Molecular weight:
32903
Reactions
L-glutamine + H(2)O = L-glutamate + NH(3).
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:
gltJ
Uniprot ID:
P0AER3
Molecular weight:
27502
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:
gltK
Uniprot ID:
P0AER5
Molecular weight:
24914

Transporters

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:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
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:
gltJ
Uniprot ID:
P0AER3
Molecular weight:
27502
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:
gltK
Uniprot ID:
P0AER5
Molecular weight:
24914
General function:
Involved in glutamate:sodium symporter activity
Specific function:
Catalyzes the sodium-dependent uptake of extracellular glutamate
Gene Name:
gltS
Uniprot ID:
P0AER8
Molecular weight:
42425