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Chemical Compound Review

glutamate     (2R)-2-aminopentanedioic acid

Synonyms: PDGA, D-Glu, D-glutamate, H-D-Glu-OH, Lopac-G-2128, ...
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Disease relevance of D-glutamate


Psychiatry related information on D-glutamate


High impact information on D-glutamate

  • DQ2 and DQ8 bind the epitopes so that the glutamic acid residues created by deamidation are accommodated in pockets that have a preference for negatively charged side chains [11].
  • We classified 56 consecutive Japanese adults with type 1 diabetes according to the presence or absence of glutamic acid decarboxylase antibodies (their presence is a marker of autoimmunity) and compared their clinical, serologic, and pathological characteristics [3].
  • All members of this family have glutamic acid residues modified to gamma-carboxyglutamic acids (Gla) by a specific gamma-carboxylase using vitamin K as a cofactor [12].
  • The modified glutamic acid residues of Gla proteins confer a high affinity for mineral ions such as calcium, phosphate and hydroxyapatite crystals, the mineral components of the skeletal ECM [12].
  • In a three-generation French family with monilethrix of a milder and variable phenotype, we detected another heterozygous point mutation in the same glutamic acid codon of hHb6, which resulted in a conservative aspartic acid substitution (Glu 410 Asp) [13].

Chemical compound and disease context of D-glutamate


Biological context of D-glutamate


Anatomical context of D-glutamate


Associations of D-glutamate with other chemical compounds

  • gamma-Carboxyglutamic acid residues on prothrombin are synthesized from glutamic acid on a prothrombin precursor in the liver through a vitamin K-dependent carboxylase [27].
  • Catalysis appears to involve water-mediated proton extraction from the substrate lysine by a glutamic acid general base and a backbone amide that stabilizes the transition-state reaction intermediate [28].
  • We propose that these codons do not represent termination codons in P. primaurelia but instead code for glutamic acid or glutamine and that the in vitro translation of Paramecium mRNAs is blocked by their presence [29].
  • Molecular characterization of one of the genes revealed that the twelfth codon was GAA instead of GGA of the normal allele, encoding glutamic acid in place of glycine [30].
  • Mere replacement of the single corresponding alanine residue in the Oct-2 homeo domain with the key glutamic acid residue is sufficient to confer on the Oct-2 homeo domain the ability to associate with VP16 in vitro and respond to VP16-induced positive control in vivo [31].

Gene context of D-glutamate

  • A glutamic acid deletion (DeltaE) in the AAA+ protein torsinA causes DYT1 dystonia [32].
  • To understand the role of Pak1 in mammary glands, we developed a murine model expressing constitutively active Thr423 glutamic acid Pak1 driven by the beta-lactoglobulin promoter [33].
  • Replacement of Y617 with a negatively charged glutamic acid (E) suppressed Btk-mediated phospholipase Cgamma2 activation and calcium response in DT-40 cells, whereas Akt activation was not affected [34].
  • However, the polypeptide, now named PEC-60 (peptide with N-terminal glutamic acid, C-terminal cysteine, and a total of 60 residues), was found not to inhibit trypsin [35].
  • We report here that cells expressing cdc28-E19 (in which Tyr-19 is replaced by glutamic acid) perform Start-related functions, complete DNA synthesis, and exhibit high levels of Clb2-associated kinase activity but are unable to form bipolar spindles [36].

Analytical, diagnostic and therapeutic context of D-glutamate


  1. Autoantibodies to glutamic acid decarboxylase in a patient with stiff-man syndrome, epilepsy, and type I diabetes mellitus. Solimena, M., Folli, F., Denis-Donini, S., Comi, G.C., Pozza, G., De Camilli, P., Vicari, A.M. N. Engl. J. Med. (1988) [Pubmed]
  2. Glutamic acid in spinal-cord gray matter in Friedreich's ataxia. Butterworth, R.F., Giguère, J.F. N. Engl. J. Med. (1982) [Pubmed]
  3. A novel subtype of type 1 diabetes mellitus characterized by a rapid onset and an absence of diabetes-related antibodies. Osaka IDDM Study Group. Imagawa, A., Hanafusa, T., Miyagawa, J., Matsuzawa, Y. N. Engl. J. Med. (2000) [Pubmed]
  4. Diabetes induced by Coxsackie virus: initiation by bystander damage and not molecular mimicry. Horwitz, M.S., Bradley, L.M., Harbertson, J., Krahl, T., Lee, J., Sarvetnick, N. Nat. Med. (1998) [Pubmed]
  5. Cloning of cDNA for the glutamate-binding subunit of an NMDA receptor complex. Kumar, K.N., Tilakaratne, N., Johnson, P.S., Allen, A.E., Michaelis, E.K. Nature (1991) [Pubmed]
  6. Differential hippocampal expression of glutamic acid decarboxylase 65 and 67 messenger RNA in bipolar disorder and schizophrenia. Heckers, S., Stone, D., Walsh, J., Shick, J., Koul, P., Benes, F.M. Arch. Gen. Psychiatry (2002) [Pubmed]
  7. Huntington disease and Tourette syndrome. II. Uptake of glutamic acid and other amino acids by fibroblasts. Comings, D.E., Goetz, I.E., Holden, J., Holtz, J. Am. J. Hum. Genet. (1981) [Pubmed]
  8. Neurochemical alterations in Huntington's chorea: a study of post-mortem brain tissue. Spokes, E.G. Brain (1980) [Pubmed]
  9. The alpha-helical to beta-strand transition in the amino-terminal fragment of the amyloid beta-peptide modulates amyloid formation. Soto, C., Castaño, E.M., Frangione, B., Inestrosa, N.C. J. Biol. Chem. (1995) [Pubmed]
  10. The B cell immune response to an idiotype-inducing peptide epitope can be inhibited by immunodominance of a neighboring epitope. Ju, S.T., Nonogaki, T., Bernatowicz, M.S., Matsueda, G.R. J. Immunol. (1993) [Pubmed]
  11. Molecular basis of celiac disease. Sollid, L.M. Annu. Rev. Immunol. (2000) [Pubmed]
  12. Mutations in the gene encoding the human matrix Gla protein cause Keutel syndrome. Munroe, P.B., Olgunturk, R.O., Fryns, J.P., Van Maldergem, L., Ziereisen, F., Yuksel, B., Gardiner, R.M., Chung, E. Nat. Genet. (1999) [Pubmed]
  13. Mutations in the hair cortex keratin hHb6 cause the inherited hair disease monilethrix. Winter, H., Rogers, M.A., Langbein, L., Stevens, H.P., Leigh, I.M., Labrèze, C., Roul, S., Taieb, A., Krieg, T., Schweizer, J. Nat. Genet. (1997) [Pubmed]
  14. Mutation of the Alzheimer's disease amyloid gene in hereditary cerebral hemorrhage, Dutch type. Levy, E., Carman, M.D., Fernandez-Madrid, I.J., Power, M.D., Lieberburg, I., van Duinen, S.G., Bots, G.T., Luyendijk, W., Frangione, B. Science (1990) [Pubmed]
  15. A covalent enzyme-substrate intermediate with saccharide distortion in a mutant T4 lysozyme. Kuroki, R., Weaver, L.H., Matthews, B.W. Science (1993) [Pubmed]
  16. A component of the multisynthetase complex is a multifunctional aminoacyl-tRNA synthetase. Cerini, C., Kerjan, P., Astier, M., Gratecos, D., Mirande, M., Sémériva, M. EMBO J. (1991) [Pubmed]
  17. A subdomain in the transmembrane domain is necessary for p185neu* activation. Cao, H., Bangalore, L., Bormann, B.J., Stern, D.F. EMBO J. (1992) [Pubmed]
  18. Novel anti-brain tumor cytotoxins specific for cancer cells. Debinski, W., Gibo, D.M., Obiri, N.I., Kealiher, A., Puri, R.K. Nat. Biotechnol. (1998) [Pubmed]
  19. A single glutamic acid residue plays a key role in the transcriptional activation function of lambda repressor. Bushman, F.D., Shang, C., Ptashne, M. Cell (1989) [Pubmed]
  20. Additive and independent responses in a single receptor: aspartate and maltose stimuli on the tar protein. Mowbray, S.L., Koshland, D.E. Cell (1987) [Pubmed]
  21. Cytoadherence of knobless Plasmodium falciparum-infected erythrocytes and its inhibition by a human monoclonal antibody. Udomsangpetch, R., Aikawa, M., Berzins, K., Wahlgren, M., Perlmann, P. Nature (1989) [Pubmed]
  22. Toxin-induced activation of the G protein p21 Rho by deamidation of glutamine. Flatau, G., Lemichez, E., Gauthier, M., Chardin, P., Paris, S., Fiorentini, C., Boquet, P. Nature (1997) [Pubmed]
  23. Role of poly(ADP-ribose) formation in DNA repair. Satoh, M.S., Lindahl, T. Nature (1992) [Pubmed]
  24. Brain neurotransmitters in dystonia musculorum deformans. Hornykiewicz, O., Kish, S.J., Becker, L.E., Farley, I., Shannak, K. N. Engl. J. Med. (1986) [Pubmed]
  25. Immunocytochemical localization of glutamic acid decarboxylase in monkey striate cortex. Hendrickson, A.E., Hunt, S.P., Wu, J.Y. Nature (1981) [Pubmed]
  26. Interaction of glutamic-acid-rich proteins with the cGMP signalling pathway in rod photoreceptors. Körschen, H.G., Beyermann, M., Müller, F., Heck, M., Vantler, M., Koch, K.W., Kellner, R., Wolfrum, U., Bode, C., Hofmann, K.P., Kaupp, U.B. Nature (1999) [Pubmed]
  27. Acquired vitamin K-dependent carboxylation deficiency in liver disease. Blanchard, R.A., Furie, B.C., Jorgensen, M., Kruger, S.F., Furie, B. N. Engl. J. Med. (1981) [Pubmed]
  28. Structure of Tetrahymena GCN5 bound to coenzyme A and a histone H3 peptide. Rojas, J.R., Trievel, R.C., Zhou, J., Mo, Y., Li, X., Berger, S.L., Allis, C.D., Marmorstein, R. Nature (1999) [Pubmed]
  29. Does Paramecium primaurelia use a different genetic code in its macronucleus? Caron, F., Meyer, E. Nature (1985) [Pubmed]
  30. Induction of mammary carcinomas in rats by nitroso-methylurea involves malignant activation of H-ras-1 locus by single point mutations. Sukumar, S., Notario, V., Martin-Zanca, D., Barbacid, M. Nature (1983) [Pubmed]
  31. A single amino acid exchange transfers VP16-induced positive control from the Oct-1 to the Oct-2 homeo domain. Lai, J.S., Cleary, M.A., Herr, W. Genes Dev. (1992) [Pubmed]
  32. The AAA+ protein torsinA interacts with a conserved domain present in LAP1 and a novel ER protein. Goodchild, R.E., Dauer, W.T. J. Cell Biol. (2005) [Pubmed]
  33. P21-activated kinase-1 phosphorylates and transactivates estrogen receptor-alpha and promotes hyperplasia in mammary epithelium. Wang, R.A., Mazumdar, A., Vadlamudi, R.K., Kumar, R. EMBO J. (2002) [Pubmed]
  34. A phosphorylation site in Bruton's tyrosine kinase selectively regulates B cell calcium signaling efficiency by altering phospholipase C-gamma activation. Guo, S., Ferl, G.Z., Deora, R., Riedinger, M., Yin, S., Kerwin, J.L., Loo, J.A., Witte, O.N. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  35. Isolation and characterization of a 60-residue intestinal peptide structurally related to the pancreatic secretory type of trypsin inhibitor: influence on insulin secretion. Agerberth, B., Söderling-Barros, J., Jörnvall, H., Chen, Z.W., Ostenson, C.G., Efendić, S., Mutt, V. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  36. Spindle pole body separation in Saccharomyces cerevisiae requires dephosphorylation of the tyrosine 19 residue of Cdc28. Lim, H.H., Goh, P.Y., Surana, U. Mol. Cell. Biol. (1996) [Pubmed]
  37. Autoantibody screening in subacute cerebellar ataxia. Trivedi, R., Mundanthanam, G., Amyes, E., Lang, B., Vincent, A. Lancet (2000) [Pubmed]
  38. Subunit III of cytochrome c oxidase is not involved in proton translocation: a site-directed mutagenesis study. Haltia, T., Saraste, M., Wikström, M. EMBO J. (1991) [Pubmed]
  39. A single base mutation in an I-A alpha-chain gene alters T-cell recognition. Griffith, I.J., Choi, E.M., Glimcher, L.H. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  40. IA-2, a transmembrane protein of the protein tyrosine phosphatase family, is a major autoantigen in insulin-dependent diabetes mellitus. Lan, M.S., Wasserfall, C., Maclaren, N.K., Notkins, A.L. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  41. L-glutamic acid, a neurotrophic factor for maintenance of acetylcholinesterase and butyrylcholinesterase in the preganglionically denervated superior cervical ganglion of the cat. Koelle, G.B., Sanville, U.J., Thampi, N.S., Wall, S.J. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
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