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Chemical Compound Review

Diglycine     2-(2- aminoethanoylamino)ethanoic acid

Synonyms: GLYGLY, Glycylglycine, Gly-Gly, Glycyl-glycine, H-Gly-Gly-OH, ...
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Disease relevance of N-GLYCYLGLYCINE


High impact information on N-GLYCYLGLYCINE

  • The purified enzyme displayed a V(max) of 7 units mg(-)1 of protein for fructose 6-phosphate cleavage (at 30 degrees C, pH 8.5 in 50 mm glycylglycine buffer) [6].
  • Although 32% of the wild-type hydrolysis activity was retained in this mutant, the activity could not be enhanced by addition of an acceptor substrate, glycylglycine, indicating that the transpeptidation reaction was specifically prevented [7].
  • 5. In contrast, acyl group transfer from cathepsin B to glycylglycine and L-leucylglycine depended on a group with a pKa of about 4 [8].
  • Limited tryptic digestion of active ubiquitin yields the inactive, later eluting form and the dipeptide glycylglycine [9].
  • We have used a stopped flow rapid reaction pH apparatus to investigate the carbamate equilibrium in glycylglycine solutions and in three biological tissues, human plasma, sheep muscle, and sheep brain, as well as to investigate the kinetics of carbamate formation in glyclyglycine solution and in human plasma [10].

Chemical compound and disease context of N-GLYCYLGLYCINE

  • When intact E. coli cells are photolyzed at approximately 350 nm in the presence of the photolabile dipeptide, their ability to transport either glycylglycine or unphotolyzed glycyl-4-azido-2-nitro-L-phenylalanine is irreversibly inhibited, but their ability to transport arginine is unaffected [2].
  • To investigate this notion further, intracellular accumulation and cytotoxicity of DXR coupled to several small peptides, such as glycylglycine (diGly), glycylglycylglycine (triGly), reduced glutathione (GSH) and oxidized glutathione (GSSG), were investigated using DXR-sensitive (AH66P) and DXR-resistant (AH66DR) rat hepatoma cell lines [11].

Biological context of N-GLYCYLGLYCINE

  • Difference spectra of the acylation of chymotrypsin by glycylglycine p-nitrophenyl ester have been obtained by averaging ten stopped-flow shots and show good signal-to-noise ratio without smoothing [12].
  • The density of [125I]iodoclonidine binding sites in glycylglycine buffer was similar to that labeled by [3H]RX821002 [13].
  • The two intermediate radicals, deamination and H-abstraction radicals, were produced in the initial interactions of glycylglycine with reactive species (e-aq, OH, H) formed in H2O [14].
  • Although glycylglycine exists mainly in the zwitterionic form at pH 7.30, it induced marked depolarization in the membrane potential and reduction in the input resistance both in the presence and absence of Na+ in the medium [15].

Anatomical context of N-GLYCYLGLYCINE


Associations of N-GLYCYLGLYCINE with other chemical compounds


Gene context of N-GLYCYLGLYCINE

  • Lack of significant effect of L(+)-glutamate on serum gamma-glutamyltransferase activity determined in the presence of glycylglycine [26].
  • The presence of glycylglycine in the medium during photolysis protects the cells against the light-dependent inactivation of dipeptide transport [2].
  • No increase in gamma-glutamyltransferase activity determined in human sera at 25, 30, or 37 degrees C could be demonstrated when L(+)-glutamate, 10 to 5000 mumol/liter, was incorporated into reaction media containing glycylglycine, 40 mmol/liter [26].
  • Staphylococcus simulans biovar staphylolyticus produces an extracellular glycylglycine endopeptidase (lysostaphin) that lyses other staphylococci by hydrolyzing the cross bridges in their cell wall peptidoglycans [27].
  • Quantum chemical and RRKM calculations were carried out on protonated glycylglycine in order to determine the atomic details of the main fragmentation pathways leading to formation of a1 and y1 ions [28].

Analytical, diagnostic and therapeutic context of N-GLYCYLGLYCINE


  1. Cytotoxicity of S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine in isolated rat kidney cells. Lash, L.H., Anders, M.W. J. Biol. Chem. (1986) [Pubmed]
  2. Photoaffinity inhibition of dipeptide transport in Escherichia coli. Staros, J.V., Knowles, J.R. Biochemistry (1978) [Pubmed]
  3. Mechanism and suppression of lysostaphin resistance in oxacillin-resistant Staphylococcus aureus. Climo, M.W., Ehlert, K., Archer, G.L. Antimicrob. Agents Chemother. (2001) [Pubmed]
  4. Impaired intestinal absorption of dipeptide in tropical sprue patients in India. Hellier, M.D., Ganapathy, V., Gammon, A., Mathan, V.I., Radhakrishnan, A.N. Clin. Sci. (1980) [Pubmed]
  5. Antimicrobial activity of lysostaphin and a Listeria monocytogenes bacteriophage endolysin produced and secreted by lactic acid bacteria. Turner, M.S., Waldherr, F., Loessner, M.J., Giffard, P.M. Syst. Appl. Microbiol. (2007) [Pubmed]
  6. Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases. Schurmann, M., Sprenger, G.A. J. Biol. Chem. (2001) [Pubmed]
  7. Significance of Arg-107 and Glu-108 in the catalytic mechanism of human gamma-glutamyl transpeptidase. Identification by site-directed mutagenesis. Ikeda, Y., Fujii, J., Taniguchi, N. J. Biol. Chem. (1993) [Pubmed]
  8. The pH dependency of bovine spleen cathepsin B-catalyzed transfer of N alpha-benzyloxycarbonyl-L-lysine from p-nitrophenol to water and dipeptide nucleophiles. Comparisons with papain. Bajkowski, A.S., Frankfater, A. J. Biol. Chem. (1983) [Pubmed]
  9. Stimulation of ATP-dependent proteolysis requires ubiquitin with the COOH-terminal sequence Arg-Gly-Gly. Wilkinson, K.D., Audhya, T.K. J. Biol. Chem. (1981) [Pubmed]
  10. The carbamate reaction of glycylglycine, plasma, and tissue extracts evaluated by a pH stopped flow apparatus. Gros, G., Forster, R.E., Lin, L. J. Biol. Chem. (1976) [Pubmed]
  11. Drug conjugate of doxorubicin with glutathione is a potent reverser of multidrug resistance in rat hepatoma cells. Asakura, T., Takahashi, N., Takada, K., Inoue, T., Ohkawa, K. Anticancer Drugs (1997) [Pubmed]
  12. A stopped-flow apparatus for infrared spectroscopy of aqueous solutions. White, A.J., Drabble, K., Wharton, C.W. Biochem. J. (1995) [Pubmed]
  13. Pharmacological characterization of [3H]idazoxan, [3H]RX821002 and p-[125I]iodoclonidine binding to alpha 2-adrenoceptors in rat cerebral cortical membranes. Wallace, D.R., Muskardin, D.T., Zahniser, N.R. Eur. J. Pharmacol. (1994) [Pubmed]
  14. Measurement of products from X-irradiated glycylglycine in oxygen-free aqueous solutions. Yoshida, H., Turner, J.E., Bolch, W.E., Jacobson, K.B., Garrison, W.M. Radiat. Res. (1992) [Pubmed]
  15. Sodium-independent, hydrogen ion-dependent changes in membrane potential and conductance induced by dipeptides in Triturus enterocytes. Shimada, T., Hoshi, T. Jpn. J. Physiol. (1986) [Pubmed]
  16. Carnosinase activity of human gastrointestinal mucosa. Sadikali, F., Darwish, R., Watson, W.C. Gut (1975) [Pubmed]
  17. Facile penetration of the Staphylococcus aureus capsule by lysostaphin. King, B.F., Biel, M.L., Wilkinson, B.J. Infect. Immun. (1980) [Pubmed]
  18. Changes in the activity of gamma-glutamyl transpeptidase in brain microvessels, astroglial cells and synaptosomes derived from rats with hepatic encephalopathy. Stastný, F., Hilgier, W., Albrecht, J., Lisý, V. Neurosci. Lett. (1988) [Pubmed]
  19. Effect of hydrogen ion-gradient on carrier-mediated transport of glycylglycine across brush border membrane vesicles from rabbit small intestine. Takuwa, N., Shimada, T., Matsumoto, H., Himukai, M., Hoshi, T. Jpn. J. Physiol. (1985) [Pubmed]
  20. The characteristics of carnosine transport and carnosine-induced electrical phenomena by the everted intestine of guinea pig. Himukai, M. Jpn. J. Physiol. (1985) [Pubmed]
  21. Identity of maleate-stimulated glutaminase with gamma-glutamyl transpeptidase in rat kidney. Tate, S.S., Meister, A. J. Biol. Chem. (1975) [Pubmed]
  22. Application of response surface methodology to the assay of gamma-glutamyltransferase. London, J.W., Shaw, L.M., Theodorsen, L., Stromme, J.H. Clin. Chem. (1982) [Pubmed]
  23. A theoretical study of potassium cation binding to glycylglycine (GG) and alanylalanine (AA) dipeptides. Wong, C.H., Ma, N.L., Tsang, C.W. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  24. Copper(II)- cis, cis-1,3,5-triaminocyclohexane complex-promoted hydrolysis of dipeptides: kinetic, speciation and structural studies. Fujii, Y., Kiss, T., Gajda, T., Tan, X.S., Sato, T., Nakano, Y., Hayashi, Y., Yashiro, M. J. Biol. Inorg. Chem. (2002) [Pubmed]
  25. gamma-Glutamyltranspeptidase from Escherichia coli K-12: purification and properties. Suzuki, H., Kumagai, H., Tochikura, T. J. Bacteriol. (1986) [Pubmed]
  26. Lack of significant effect of L(+)-glutamate on serum gamma-glutamyltransferase activity determined in the presence of glycylglycine. Gerhardt, W., Persijn, P., Rosalki, S.B. Clin. Chem. (1975) [Pubmed]
  27. The lysostaphin endopeptidase resistance gene (epr) specifies modification of peptidoglycan cross bridges in Staphylococcus simulans and Staphylococcus aureus. DeHart, H.P., Heath, H.E., Heath, L.S., LeBlanc, P.A., Sloan, G.L. Appl. Environ. Microbiol. (1995) [Pubmed]
  28. Theoretical study of the main fragmentation pathways for protonated glycylglycine. Paizs, B., Suhai, S. Rapid Commun. Mass Spectrom. (2001) [Pubmed]
  29. Impairment of jejunal absorption rate of carnosine by glycylglycine in man in vivo. Cook, G.C. Gut (1976) [Pubmed]
  30. Comparison of efficacy of a glucose/glycine/glycylglycine electrolyte solution versus the standard WHO/ORS in diarrheic dehydrated children. Pizarro, D., Posada, G., Mahalanabis, D., Sandí, L. J. Pediatr. Gastroenterol. Nutr. (1988) [Pubmed]
  31. Effect of dipolar ions on the entropy-driven polymerization of tobacco mosaic virus protein. Lauffer, M.A., Shalaby, R.A. Arch. Biochem. Biophys. (1985) [Pubmed]
  32. Bicarbonate: the alternative buffer for peritoneal dialysis. Passlick-Deetjen, J., Kirchgessner, J. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (1996) [Pubmed]
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