Glutamyl-glutamic acid

• CAT Number: I014396
• CAS Number: 3929-61-1
• Molecular Formula: C10H16N2O7
• Molecular Weight: 276.24
• Purity: ≥95%
• Synonyms: Glutamyl-glutamic acid; Dipotassium glutamyl-glutamate; Glu-glu; N-L-alpha-Glutamyl-L-glutamic acid;;L-glutamyl-L-glutamic acid
• Solubility: Soluble in DMSO
• IUPAC Name: (2S)-2-[[(2S)-2-amino-4-carboxybutanoyl]amino]pentanedioic acid
• InChI: InChI=1S/C10H16N2O7/c11-5(1-3-7(13)14)9(17)12-6(10(18)19)2-4-8(15)16/h5-6H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
• InChIKey: KOSRFJWDECSPRO-WDSKDSINSA-N
• SMILES: O=C(O)CC[C@@H](C(O)=O)NC([C@H](CCC(O)=O)N)=O

Glutamyl-glutamic acid (Cat.No:I014396) is a dipeptide consisting of two glutamic acid molecules joined together. It is involved in various biological processes and functions as a neurotransmitter in the central nervous system. Glutamyl-glutamic acid plays a crucial role in the regulation of neuronal activity, learning, and memory, and its dysfunction has been linked to neurological disorders.

Reference

1: Zhao CJ, Gänzle MG. Synthesis of Taste-Active γ-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568. Epub 2016 Sep 29. PubMed PMID: 27641253.2: Juhl K, Christensen A, Persson M, Ploug M, Kjaer A. Peptide-Based Optical uPAR Imaging for Surgery: In Vivo Testing of ICG-Glu-Glu-AE105. PLoS One. 2016 Feb 1;11(2):e0147428. doi: 10.1371/journal.pone.0147428. eCollection 2016. PubMed PMID: 26828431; PubMed Central PMCID: PMC4734687.3: Shim J, Son HJ, Kim Y, Kim KH, Kim JT, Moon H, Kim MJ, Misaka T, Rhyu MR. Modulation of sweet taste by umami compounds via sweet taste receptor subunit hT1R2. PLoS One. 2015 Apr 8;10(4):e0124030. doi: 10.1371/journal.pone.0124030. eCollection 2015. PubMed PMID: 25853419; PubMed Central PMCID: PMC4390298.4: Kim MJ, Son HJ, Kim Y, Misaka T, Rhyu MR. Umami-bitter interactions: the suppression of bitterness by umami peptides via human bitter taste receptor. Biochem Biophys Res Commun. 2015 Jan 9;456(2):586-90. doi: 10.1016/j.bbrc.2014.11.114. Epub 2014 Dec 6. PubMed PMID: 25490385.5: Wang YY, Li YD, Liu JB, Ran XX, Guo YY, Ren NN, Chen X, Jiang H, Li YQ. Characterization and evolutionary implications of the triad Asp-Xxx-Glu in group II phosphopantetheinyl transferases. PLoS One. 2014 Jul 18;9(7):e103031. doi: 10.1371/journal.pone.0103031. eCollection 2014. PubMed PMID: 25036863; PubMed Central PMCID: PMC4103896.6: Vavrusova M, Skibsted LH. Calcium binding to dipeptides of aspartate and glutamate in comparison with orthophosphoserine. J Agric Food Chem. 2013 Jun 5;61(22):5380-4. doi: 10.1021/jf400741e. Epub 2013 May 24. PubMed PMID: 23682986.7: Schor M, Bolhuis PG. The self-assembly mechanism of fibril-forming silk-based block copolymers. Phys Chem Chem Phys. 2011 Jun 14;13(22):10457-67. doi: 10.1039/c0cp02842h. Epub 2011 Apr 18. PubMed PMID: 21503301.8: Clavel T, Saalfrank A, Charrier C, Haller D. Isolation of bacteria from mouse caecal samples and description of Bacteroides sartorii sp. nov. Arch Microbiol. 2010 Jun;192(6):427-35. doi: 10.1007/s00203-010-0568-6. Epub 2010 Apr 6. PubMed PMID: 20369227.9: Borgwardt K, Bonifatius S, Gardemann A. Acidic peptides enhanced genistein-dependent inhibition of human platelet aggregation: potential protective effect of digestible peptides plus genistein against atherosclerosis. Nutr Res. 2008 Aug;28(8):523-31. doi: 10.1016/j.nutres.2008.03.017. PubMed PMID: 19083455.10: Steghens JP, Flourié F, Arab K, Collombel C. Fast liquid chromatography-mass spectrometry glutathione measurement in whole blood: micromolar GSSG is a sample preparation artifact. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Dec 25;798(2):343-9. PubMed PMID: 14643515.11: Takahashi N, Sato T. Dipeptide utilization by the periodontal pathogens Porphyromonas gingivalis, Prevotella intermedia, Prevotella nigrescens and Fusobacterium nucleatum. Oral Microbiol Immunol. 2002 Feb;17(1):50-4. PubMed PMID: 11860556.12: Ellsworth JL, Hamacher N, Bagwell N, West JW. Detection of Glu-Glu-tagged proteins in mammalian cell culture media by dot immunoblotting. Biotechniques. 2000 May;28(5):934-6, 937. PubMed PMID: 10818700.13: Kostanyan IA, Navolotskaya EV, Nurieva RI, Zav’ialov VP, Lipkin VM. [Interaction of L-glutamic acid with human T-lymphocytes]. Bioorg Khim. 1997 Oct;23(10):805-8. Russian. PubMed PMID: 9490616.14: Tsukida T, Hiramatsu Y, Tsujishita H, Kiyoi T, Yoshida M, Kurokawa K, Moriyama H, Ohmoto H, Wada Y, Saito T, Kondo H. Studies on selection blockers. 5. Design, synthesis, and biological profile of sialyl Lewis x mimetics based on modified serine-glutamic acid dipeptides. J Med Chem. 1997 Oct 24;40(22):3534-41. Erratum in: J Med Chem 1998 Jan 15;41(2):262. PubMed PMID: 9357520.15: Jeon CJ, Gurski MR, Mize RR. Glutamate containing neurons in the cat superior colliculus revealed by immunocytochemistry. Vis Neurosci. 1997 Mar-Apr;14(2):387-93. PubMed PMID: 9147489.16: Jeon CJ, Hartman MK, Mize RR. Glutamate-like immunoreactivity in the cat superior colliculus and visual cortex: further evidence that glutamate is the neurotransmitter of the corticocollicular pathway. Vis Neurosci. 1997 Jan-Feb;14(1):27-37. PubMed PMID: 9057266.17: Sasaki M, Bosman BW, Tan PS. Comparison of proteolytic activities in various lactobacilli. J Dairy Res. 1995 Nov;62(4):601-10. PubMed PMID: 8568030.18: Ohnishi M, Sugawara R, Kusano T. Taste responses to the optical isomers of potassium warfarin and dipotassium glutamyl glutamate and the synergistic response to a mixture of both substances in mice. Biosci Biotechnol Biochem. 1995 Jun;59(6):1002-6. PubMed PMID: 7612987.19: Charpiot P, Calaf R, Chareyre C, Rolland PH, Garçon D. Rapid determination of desmosine and isodesmosine in tissue hydrolysates by isocratic high performance liquid chromatography and precolumn derivatization. Amino Acids. 1994 Feb;6(1):57-63. doi: 10.1007/BF00808123. PubMed PMID: 24190743.20: Fournier D, Mouton C. Phenotypic characterization of human and animal biotypes within the species Porphyromonas gingivalis. Res Microbiol. 1993 Jul-Aug;144(6):435-44. PubMed PMID: 8190990.