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Glutamyl-Glutamine

July 21, 2017
Common Name

Glutamyl-Glutamine Description

Glutamyl-Glutamine is a dipeptide composed of glutamate and glutamine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

MOLSDFPDBSMILESInChI

Structure for HMDB28817 (Glutamyl-Glutamine)

Synonyms

Value Source e-Q DipeptideHMDB EQ dipeptideHMDB Glu-GLNHMDB Glutamate glutamine dipeptideHMDB Glutamate-glutamine dipeptideHMDB GlutamylglutamineHMDB L-Glutamyl-L-glutamineHMDB

Chemical Formlia

C10H16N3O6 Average Molecliar Weight

274.2505 Monoisotopic Molecliar Weight

274.103910259 IUPAC Name

4-amino-4-[(3-carbamoyl-1-carboxypropyl)carbamoyl]butanoate Traditional Name

4-amino-4-[(3-carbamoyl-1-carboxypropyl)carbamoyl]butanoate CAS Registry Number

Not Available SMILES

NC(CCC([O-])=O)C(=O)NC(CCC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C10H17N3O6/c11-5(1-4-8(15)16)9(17)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,17)(H,15,16)(H,18,19)/p-1

InChI Key

MGHKSHCBDXNTHX-UHFFFAOYSA-M Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Glutamine and derivatives
  • Glutamic acid and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Amino fatty acids
  • N-acyl amines
  • Dicarboxylic acids and derivatives
  • Secondary carboxylic acid amides
  • Primary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Carbonyl compounds
  • Organic oxides
  • Organic anions

    • Substituents

  • Alpha-dipeptide
  • Glutamine or derivatives
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amino fatty acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic anion
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-5.17Extrapolated

    Predicted Properties

    Property Value Source Water Solubility13.4 mg/mLALOGPS logP-3.4ALOGPS logP-5.2ChemAxon logS-1.3ALOGPS pKa (Strongest Acidic)3.24ChemAxon pKa (Strongest Basic)8.45ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area175.64 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity72.03 m3·mol-1ChemAxon Polarizability25.83 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB28817 Metagene Link

    HMDB28817 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: BVT-14225

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
    2. Hammond JW, Potter M, Sim KG, Wilcken B: Reduced glutathione, gamma-glutamylcysteine, cysteine and gamma-glutamylglutamine in gamma-glutamyltransferase deficiency. J Inherit Metab Dis. 1999 May;22(3):235-9. [PubMed:10384376 ]
    3. Sandberg M, Li X, Folestad S, Weber SG, Orwar O: Liquid chromatographic determination of acidic beta-aspartyl and gamma-glutamyl peptides in extracts of rat brain. Anal Biochem. 1994 Feb 15;217(1):48-61. [PubMed:7911284 ]
    4. El Sayed AS, Fujimoto S, Yamada C, Suzuki H: Enzymatic synthesis of gamma-glutamylglutamine, a stable glutamine analogue, by gamma-glutamyltranspeptidase from Escherichia coli K-12. Biotechnol Lett. 2010 Dec;32(12):1877-81. doi: 10.1007/s10529-010-0364-z. Epub 2010 Jul 31. [PubMed:20676917 ]
    5. Do KQ, Trabesinger AH, Kirsten-Kruger M, Lauer CJ, Dydak U, Hell D, Holsboer F, Boesiger P, Cuenod M: Schizophrenia: glutathione deficit in cerebrospinal fluid and prefrontal cortex in vivo. Eur J Neurosci. 2000 Oct;12(10):3721-8. [PubMed:11029642 ]
    6. Yang D, Liu X, Jiang X, Liu Y, Ying W, Wang H, Bai H, Taylor WD, Wang Y, Clamme JP, Co E, Chivukula P, Tsang KY, Jin Y, Yu L: Effect of molecular weight of PGG-paclitaxel conjugates on in vitro and in vivo efficacy. J Control Release. 2012 Jul 10;161(1):124-31. doi: 10.1016/j.jconrel.2012.04.010. Epub 2012 Apr 12. [PubMed:22521595 ]
    7. Jaeken J: Cerebrospinal fluid as a tool in the diagnosis of neurometabolic diseases: amino acid analysis before and after acid hydrolysis. Eur J Pediatr. 1994;153(7 Suppl 1):S86-9. [PubMed:7957393 ]
    8. Li X, Orwar O, Revesjo C, Sandberg M: Gamma-glutamyl peptides and related amino acids in rat hippocampus in vitro: effect of depolarization and gamma-glutamyl transpeptidase inhibition. Neurochem Int. 1996 Aug;29(2):121-8. [PubMed:8837040 ]
    9. Yang D, Van S, Jiang X, Yu L: Novel free paclitaxel-loaded poly(L-gamma-glutamylglutamine)-paclitaxel nanoparticles. Int J Nanomedicine. 2011 Jan 6;6:85-91. doi: 10.2147/IJN.S15839. [PubMed:21289985 ]
    10. Orwar O, Li X, Andine P, Bergstrom CM, Hagberg H, Folestad S, Sandberg M: Increased intra- and extracellular concentrations of gamma-glutamylglutamate and related dipeptides in the ischemic rat striatum: involvement of glutamyl transpeptidase. J Neurochem. 1994 Oct;63(4):1371-6. [PubMed:7931288 ]
    11. Suzuki H, Izuka S, Minami H, Miyakawa N, Ishihara S, Kumagai H: Use of bacterial gamma-glutamyltranspeptidase for enzymatic synthesis of gamma-D-glutamyl compounds. Appl Environ Microbiol. 2003 Nov;69(11):6399-404. [PubMed:14602592 ]

    PMID: 10822046

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