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Chemical Compound Review

AC1NUFKI     3-[[1-[[1-[[2-amino-1-[[1-[2- [1-(2,5-dioxo...

Synonyms: NSC-267431
 
 
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Disease relevance of U 6658

 

High impact information on U 6658

  • The transferase activity has an optimal pH of 7.5- 8.5, requires Mn2+, is unaffected by tunicamycin or amphomycin, and is strongly inhibited by UDP [4].
  • The inhibitory effect of the lipopeptide antibiotic amphomycin on the mechanism of mannosylphosphoryldolichol biosynthesis by calf brain rough endoplasmic reticulum membranes has been studied extensively [5].
  • These data demonstrated that amphomycin interacted with the active site of the glycosyl-carrier lipid (Dol-P), thereby preventing its participation at the enzymatic reaction [5].
  • On the other hand, when mannosylphosphoryldolichol synthase activity was measured in the presence of amphomycin and as a function of dolichylmonophosphate (Dol-P) concentrations, the shape of the substrate velocity curve changed from a rectangular hyperbola to a sigmoid [5].
  • Inhibition of glycosylation by amphomycin and sugar nucleotide analogs PP36 and PP55 indicates that Haloferax volcanii beta-glucosylates both glycoproteins and glycolipids through lipid-linked sugar intermediates: evidence for three novel glycoproteins and a novel sulfated dihexosyl-archaeol glycolipid [6].
 

Biological context of U 6658

 

Anatomical context of U 6658

  • Furthermore, exposure of capillary endothelial cells to amphomycin, followed by the monoclonal antibody to amphomycin, followed sequentially by staining with FITC-conjugated goat anti-mouse IgG and examination under a fluorescent microscope gives intense fluorescence at the perinuclear region of the cell with a structure reminiscent of the ER [8].
  • Amphomycin at very high concentration (500 micrograms mL-1) was toxic to embryos but at concentrations up to 250 micrograms mL-1 had no effect on compaction and development of blastocysts [9].
 

Associations of U 6658 with other chemical compounds

  • In vivo and in vitro inhibition of lipid-linked saccharide and glycoprotein synthesis in plants by amphomycin [10].
  • In addition. the antibiotic amphomycin selectively inhibited the formation of mannosylated products suggesting polyprenolmonophosphate-mannose (C15 50-P-Man) was the immediate mannose donor in all mannosylation reactions observed [11].
 

Gene context of U 6658

 

Analytical, diagnostic and therapeutic context of U 6658

  • The antibody belongs to the IgG+IgM subclasses and is specific for amphomycin when analyzed by the enzyme-linked immunoassay and immunoblot procedures [8].

References

  1. Studies on bacterial cell wall inhibitors. X. Properties of phosph-N-acetylmuramoyl-pentapeptide-transferase in peptidoglycan synthesis of Bacillus megaterium and its inhibition by amphomycin. Tanaka, H., Oiwa, R., Matsukura, S., Inokoshi, J., Omura, S. J. Antibiot. (1982) [Pubmed]
  2. Phospho-MurNAc-pentapeptide translocase (MraY) as a target for antibacterial agents and antibacterial proteins. Bugg, T.D., Lloyd, A.J., Roper, D.I. Infectious disorders drug targets. (2006) [Pubmed]
  3. A recent approach to the study of dolichyl monophosphate topology in the rough endoplasmic reticulum. Banerjee, D.K. Acta Biochim. Pol. (1994) [Pubmed]
  4. Biosynthesis of O-N-acetylglucosamine-linked glycans in Trypanosoma cruzi. Characterization of the novel uridine diphospho-N-acetylglucosamine:polypeptide N-acetylglucosaminyltransferase-catalyzing formation of N-acetylglucosamine alpha1-->O-threonine. Previato, J.O., Sola-Penna, M., Agrellos, O.A., Jones, C., Oeltmann, T., Travassos, L.R., Mendonça-Previato, L. J. Biol. Chem. (1998) [Pubmed]
  5. Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. Banerjee, D.K. J. Biol. Chem. (1989) [Pubmed]
  6. Inhibition of glycosylation by amphomycin and sugar nucleotide analogs PP36 and PP55 indicates that Haloferax volcanii beta-glucosylates both glycoproteins and glycolipids through lipid-linked sugar intermediates: evidence for three novel glycoproteins and a novel sulfated dihexosyl-archaeol glycolipid. Zhu, B.C., Drake, R.R., Schweingruber, H., Laine, R.A. Arch. Biochem. Biophys. (1995) [Pubmed]
  7. Amphomycin: effect of the lipopeptide antibiotic on the glycosylation and extraction of dolichyl monophosphate in calf brain membranes. Banerjee, D.K., Scher, M.G., Waechter, C.J. Biochemistry (1981) [Pubmed]
  8. Monoclonal antibody to amphomycin. A tool to study the topography of dolichol monophosphate in the membrane. Banerjee, D.K., Diaz, A.M., Campos, T.M., Grande, C., Kozek, W.J., Baksi, K. Carbohydr. Res. (1992) [Pubmed]
  9. Participation of glucose in the synthesis of glycoproteins in preimplantation mouse embryos. Wales, R.G., Hunter, J. Reprod. Fertil. Dev. (1990) [Pubmed]
  10. In vivo and in vitro inhibition of lipid-linked saccharide and glycoprotein synthesis in plants by amphomycin. Ericson, M.C., Gafford, J.T., Elbein, A.D. Arch. Biochem. Biophys. (1978) [Pubmed]
  11. Synthetic mannosides act as acceptors for mycobacterial alpha1-6 mannosyltransferase. Brown, J.R., Field, R.A., Barker, A., Guy, M., Grewal, R., Khoo, K.H., Brennan, P.J., Besra, G.S., Chatterjec, D. Bioorg. Med. Chem. (2001) [Pubmed]
 
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