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Chemical Compound Review

6-diazo-5-oxo-L-norleucine     5-amino-5-carboxy-1-diazonio- pent-1-en-2...

Synonyms: AG-K-74743, NSC7365, CTK5E2925, CTK9A4292, AC1L18MC, ...
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Disease relevance of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium


High impact information on 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium


Chemical compound and disease context of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium


Biological context of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium


Anatomical context of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium


Associations of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium with other chemical compounds


Gene context of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium

  • On the other hand, inhibition by 6-diazo-5-oxo-l-norleucine of the rate-limiting enzyme in hexosamine biosynthesis blunted EPA-induced stimulation of leptin mRNA expression and its secretion [25].
  • Inactivation of rat renal phosphate-dependent glutaminase by 6-diazo-5-oxo-L-norleucine occurs only under conditions where the enzyme is catalytically active [14].
  • Radiolabeled protein is not observed (i) when the wild-type enzyme is incubated with 6-diazo-5-oxo-L-norleucine (DON) prior to reaction with [14C]glutamine or (ii) when the C1A AS-B mutant is incubated with [14C]-L-glutamine [26].
  • The mechanism of 6-diazo-5-oxo-L-norleucine inhibition appeared to be the same as that induced by NH4+, because nitrogenase activity could be restored in vitro by activating enzyme and Mn2+ [21].
  • GMP is a considerably more potent inhibitor of the human lymphoblast enzyme than is AMP; 6-diazo-5-oxo-L-norleucine inhibits only glutamine-dependent activity and has no effect on ammonia-dependent activity [27].

Analytical, diagnostic and therapeutic context of 5-amino-5-carboxy-2-hydroxy-pent-1-ene-1-diazonium

  • Using an organ culture model in which fetal murine thymuses explanted on gestational day 14 undergo phenotypic maturation from CD3-CD4-CD8- to CD3+CD4+/CD8+, the consequences of inhibiting GAG synthesis with 6-diazo-5-oxo-L-norleucine (DON) were explored [28].


  1. Enhancement of antitumor activity of glutamine antagonists 6-diazo-5-oxo-L-norleucine and acivicin in cell culture by glutaminase-asparaginase. Rosenfeld, H., Roberts, J. Cancer Res. (1981) [Pubmed]
  2. Uptake of glutamine antimetabolites 6-diazo-5-oxo-L-norleucine (DON) and acivicin in sensitive and resistant tumor cell lines. Huber, K.R., Rosenfeld, H., Roberts, J. Int. J. Cancer (1988) [Pubmed]
  3. Antiviral effect of 6-diazo-5-oxo-L-norleucine, antagonist of gamma-glutamyl transpeptidase, on replication of human parainfluenza virus type 2. Nishio, M., Tsurudome, M., Bando, H., Komada, H., Ito, Y. J. Gen. Virol. (1990) [Pubmed]
  4. Phase I study and clinical pharmacology of 6-diazo-5-oxo-L-norleucine (DON). Rahman, A., Smith, F.P., Luc, P.T., Woolley, P.V. Investigational new drugs. (1985) [Pubmed]
  5. Trypanosoma brucei CTP synthetase: a target for the treatment of African sleeping sickness. Hofer, A., Steverding, D., Chabes, A., Brun, R., Thelander, L. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  6. Inactivation of renal gamma-glutamyl transferase by 6-diazo-5-oxo-L-norleucylglycine, an inactive precursor of affinity-labeling reagent. Inoue, M., Morino, Y. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  7. Glutaminase and glutamine synthetase activities in human cirrhotic liver and hepatocellular carcinoma. Matsuno, T., Goto, I. Cancer Res. (1992) [Pubmed]
  8. Efficacy of 6-diazo-5-oxo-L-norleucine and N-[N-gamma-glutamyl-6-diazo-5-oxo-norleucinyl]-6-diazo-5-oxo-norleucine against experimental tumors in conventional and nude mice. Ovejera, A.A., Houchens, D.P., Catane, R., Sheridan, M.A., Muggia, F.M. Cancer Res. (1979) [Pubmed]
  9. The effects of 6-diazo-5-oxo-L-norleucine, a glutamine analogue, on the structure of the major cartilage proteoglycan synthesized by cultured chondrocytes. Clark, C.C., Richards, C.F., Pacifici, M., Iozzo, R.V. J. Biol. Chem. (1987) [Pubmed]
  10. Phase II trial of 6-diazo-5-oxo-L-norleucine versus aclacinomycin-A in advanced sarcomas and mesotheliomas. Earhart, R.H., Amato, D.J., Chang, A.Y., Borden, E.C., Shiraki, M., Dowd, M.E., Comis, R.L., Davis, T.E., Smith, T.J. Investigational new drugs. (1990) [Pubmed]
  11. Mutagenicity of D- and L-azaserine, 6-diazo-5-oxo-L-norleucine and N-(N-methyl-N-nitroso-carbamyl)-L-ornithine in the Salmonella test system. Staiano, N., Everson, R.B., Cooney, D.A., Longnecker, D.S., Thorgeirsson, S.S. Mutat. Res. (1980) [Pubmed]
  12. Poliovirus and vesicular stomatitis virus replication in the presence of 6-diazo-5-oxo-L-norleucine or 2-deoxy-D-glucose. Goldstein, G., Guskey, L.E. J. Med. Virol. (1984) [Pubmed]
  13. Transport mechanisms of 6-diazo-5-oxo-L-norleucine in Escherichia coli K-12. Williams, M.V. Microbiologica (1982) [Pubmed]
  14. Inactivation of rat renal phosphate-dependent glutaminase with 6-diazo-5-oxo-L-norleucine. Evidence for interaction at the glutamine binding site. Shapiro, R.A., Clark, V.M., Curthoys, N.P. J. Biol. Chem. (1979) [Pubmed]
  15. Cell cycle phase perturbations by 6-diazo-5-oxo-L-norleucine and acivicin in normal and neoplastic human cell lines. Huber, K.R., Mayer, E.P., Mitchell, D.F., Roberts, J. Br. J. Cancer (1987) [Pubmed]
  16. Modulation of heparan sulfate biosynthesis. Effects of 6-diazo-5-oxo-L-norleucine and low glutamine on the synthesis of heparan sulfate proteoglycan by human colon carcinoma cells. Iozzo, R.V., Clark, C.C. J. Biol. Chem. (1987) [Pubmed]
  17. Post-translational alterations in newly synthesized cartilage proteoglycans induced by the glutamine analogue 6-diazo-5-oxo-L-norleucine. Time course of inhibition and recovery. Clark, C.C., Richards, C.F., Iozzo, R.V. Biochem. J. (1991) [Pubmed]
  18. Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis. Wu, G., Haynes, T.E., Li, H., Yan, W., Meininger, C.J. Biochem. J. (2001) [Pubmed]
  19. A mechanism behind the antitumour effect of 6-diazo-5-oxo-L-norleucine (DON): disruption of mitochondria. Wu, F., Lukinius, A., Bergström, M., Eriksson, B., Watanabe, Y., Långström, B. Eur. J. Cancer (1999) [Pubmed]
  20. Transport and membrane binding of the glutamine analogue 6-diazo-5-oxo-L-norleucine (DON) in Xenopus laevis oocytes. Taylor, P.M., Mackenzie, B., Hundal, H.S., Robertson, E., Rennie, M.J. J. Membr. Biol. (1992) [Pubmed]
  21. Effect of light intensity and inhibitors of nitrogen assimilation on NH4+ inhibition of nitrogenase activity in Rhodospirillum rubrum and Anabaena sp. Yoch, D.C., Gotto, J.W. J. Bacteriol. (1982) [Pubmed]
  22. Assimilation of 13NH4+ by Azospirillum brasilense grown under nitrogen limitation and excess. Westby, C.A., Enderlin, C.S., Steinberg, N.A., Joseph, C.M., Meeks, J.C. J. Bacteriol. (1987) [Pubmed]
  23. Glutamate immunoreactivity in rat cerebral cortex is reversibly abolished by 6-diazo-5-oxo-L-norleucine (DON), an inhibitor of phosphate-activated glutaminase. Conti, F., Minelli, A. J. Histochem. Cytochem. (1994) [Pubmed]
  24. Determination of 6-diazo-5-oxo-L-norleucine in plasma and urine by reversed-phase high-performance liquid chromatography of the dansyl derivative. Powis, G., Ames, M.M. J. Chromatogr. (1980) [Pubmed]
  25. Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro. Murata, M., Kaji, H., Takahashi, Y., Iida, K., Mizuno, I., Okimura, Y., Abe, H., Chihara, K. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  26. Formation and isolation of a covalent intermediate during the glutaminase reaction of a class II amidotransferase. Schnizer, H.G., Boehlein, S.K., Stewart, J.D., Richards, N.G., Schuster, S.M. Biochemistry (1999) [Pubmed]
  27. Assay of glutamine phosphoribosylpyrophosphate amidotransferase using [1-14C]phosphoribosylpyrophosphate. Boss, G.R., Idriss, S.D., Willis, R.C., Seegmiller, J.E. Anal. Biochem. (1983) [Pubmed]
  28. Regulation by heparan sulfate and interleukin 1 alpha of the ontogenic expression of T-cell receptor, CD4, and CD8 in developing thymus. Wrenshall, L.E., Cerra, F.B., Rubinstein, P., Platt, J.L. Hum. Immunol. (1993) [Pubmed]
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