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Chemical Compound Review

1-Deoxymannojirimycin     (2R,3R,4R,5R)-2- (hydroxymethyl)piperidine...

Synonyms: CHEMBL84844, SureCN329674, BSPBio_000991, CHEBI:41938, CHEBI:238719, ...
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Disease relevance of 1-Deoxymannojirimycin

  • Although the oligosaccharides of these membrane glycoproteins were greatly altered, neither dNM nor dMM interferred with their surface expression, as determined by a variety of assays, including accessibility to proteases and antibodies; neither did these drugs inhibit production of infectious virus particles [1].
  • Deoxymannojirimycin (dMM) or swainsonine (SW), which block conversion of high-mannose to complex-type N-linked glycans, strongly inhibited the production of immunoglobulin (Ig) when added to cultures of human lymphocytes together with the polyclonal B cell activators pokeweed mitogen (PWM) and Staphylococcus aureus (SAC) [2].
  • Further, murine leukemia virus, which typically does not interact efficiently with DC-SIGN(R), could do so when produced in the presence of deoxymannojirimycin [3].
  • Treatment with dMM increased the immunocapture of HIV by monoclonal antibodies 2F5 and 2G12, indicating that altering the glycosylation of viral glycoproteins increases the accessibility or reactivity of some epitopes [4].
  • Further modification of this glycoform is blocked by vaccinia virus infection or by the inhibitor deoxymannojirimycin [5].

High impact information on 1-Deoxymannojirimycin

  • The glucosidase inhibitors castanospermine and dNM, but not the mannosidase inhibitor dMM, inhibited syncytium formation and interfered with infectivity [6].
  • The crystal structure of Drosophila Golgi alpha-mannosidase II in the absence and presence of the anti-cancer agent swainsonine and the inhibitor deoxymannojirimycin reveals a novel protein fold with an active site zinc intricately involved both in the substrate specificity of the enzyme and directly in the catalytic mechanism [7].
  • Growth of GPI-HA-expressing cells in the presence of the mannosidase I inhibitor deoxymannojirimycin (dMM) abrogated the differences in carbohydrate modification and restored the ability of GPI-HA to bind erythrocytes [8].
  • The ectodomain of GPI-HA produced from cells grown in the presence or absence of dMM underwent characteristic low pH-induced conformational changes (it released its fusion peptides and became hydrophobic and proteinase sensitive) but at 0.2 and 0.4 pH units higher than wt-HA, respectively [8].
  • Additional inhibitors of the N-linked glycosylation pathway, castanospermine, deoxynojirimycin, and deoxymannojirimycin significantly decreased TEA transport, whereas swainsonine had no effect [9].

Chemical compound and disease context of 1-Deoxymannojirimycin


Biological context of 1-Deoxymannojirimycin


Anatomical context of 1-Deoxymannojirimycin


Associations of 1-Deoxymannojirimycin with other chemical compounds

  • LPL was active and secreted when trimming of the mannose residues was inhibited by deoxymannojirimycin and when addition of complex sugars was blocked using Chinese hamster ovary mutants (lec1 and lec2), indicating that these processing events are not necessary for the expression of a functional enzyme [21].
  • The relatively lengthy folding time was not due to modification of the large number of N-linked glycosylation sites on gp120, since inhibition of the first steps in oligosaccharide modification by the inhibitors deoxynojirimycin or deoxymannojirimycin did not impair the CD4-binding activity of the glycoprotein [22].
  • Tunicamycin reduces the Mr of the nascent protein to 75 kDa, but deoxymannojirimycin and swainsonine have no effect, suggesting that following initial glycosylation in the endoplasmic reticulum, the protein is not subject to processing by glycosidases in the Golgi apparatus or may bypass it entirely [23].
  • The activities were distinguished from lysosomal and Golgi alpha-mannosidases by their neutral pH optima, relatively low Km for their synthetic substrate p-nitrophenyl alpha-D-mannoside, inhibition by Zn2+ and absence of inhibition by Co2+, EDTA, low concentrations of swainsonine, or deoxymannojirimycin [24].
  • Inhibition of ER mannosidase I with deoxymannojirimycin or kifunensine had no effect on apo(a) secretion, but inhibited proteasome-mediated apo(a) ERAD even under conditions where apo(a)-CNX/CRT interaction was prevented [25].

Gene context of 1-Deoxymannojirimycin

  • When compared with their counterpart synthesized in control cells, VIP-binding proteins produced by deoxymannojirimycin- or swainsonine-treated cells were smaller in size and exhibited the expected sensitivity to Endo H [26].
  • Treatment of virus grown in the presence of dMM with endoglycosidase F1 substantially reduced binding to MBL, indicating that dMM increased MBL binding by increasing high-mannose carbohydrates on the virus [4].
  • Treatment with DMM, a mannosidase inhibitor, efficiently reduced the appearance of high molecular weight forms of CD95 after IFN-gamma treatment, and sensitized SEM and REH cells to CD95-mediated death [27].
  • In the presence of 1 mM dMM, cells synthesized Endo H-sensitive alpha 2-PI and ATIII with similar secretion rates [28].
  • Cells treated with methyl-deoxynojirimycin or with deoxymannojirimycin produced and released active lipoprotein lipase which was fully Endo H-sensitive [29].


  1. Inhibition of N-linked oligosaccharide trimming does not interfere with surface expression of certain integral membrane proteins. Burke, B., Matlin, K., Bause, E., Legler, G., Peyrieras, N., Ploegh, H. EMBO J. (1984) [Pubmed]
  2. Inhibition of N-linked oligosaccharide trimming mannosidases blocks human B cell development. Tulp, A., Barnhoorn, M., Bause, E., Ploegh, H. EMBO J. (1986) [Pubmed]
  3. Differential N-linked glycosylation of human immunodeficiency virus and Ebola virus envelope glycoproteins modulates interactions with DC-SIGN and DC-SIGNR. Lin, G., Simmons, G., Pöhlmann, S., Baribaud, F., Ni, H., Leslie, G.J., Haggarty, B.S., Bates, P., Weissman, D., Hoxie, J.A., Doms, R.W. J. Virol. (2003) [Pubmed]
  4. Glycosylation inhibitors and neuraminidase enhance human immunodeficiency virus type 1 binding and neutralization by mannose-binding lectin. Hart, M.L., Saifuddin, M., Spear, G.T. J. Gen. Virol. (2003) [Pubmed]
  5. Molecular characterization of the cellular receptor for poliovirus. Bernhardt, G., Bibb, J.A., Bradley, J., Wimmer, E. Virology (1994) [Pubmed]
  6. Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase. Gruters, R.A., Neefjes, J.J., Tersmette, M., de Goede, R.E., Tulp, A., Huisman, H.G., Miedema, F., Ploegh, H.L. Nature (1987) [Pubmed]
  7. Structure of Golgi alpha-mannosidase II: a target for inhibition of growth and metastasis of cancer cells. van den Elsen, J.M., Kuntz, D.A., Rose, D.R. EMBO J. (2001) [Pubmed]
  8. GPI- and transmembrane-anchored influenza hemagglutinin differ in structure and receptor binding activity. Kemble, G.W., Henis, Y.I., White, J.M. J. Cell Biol. (1993) [Pubmed]
  9. Inhibition of N-linked glycosylation affects organic cation transport across the brush border membrane of opossum kidney (OK) cells. Ott, R.J., Hui, A.C., Giacomini, K.M. J. Biol. Chem. (1992) [Pubmed]
  10. Non-lytic extraction and characterisation of receptors for multiple strains of rotavirus. Jolly, C.L., Beisner, B.M., Ozser, E., Holmes, I.H. Arch. Virol. (2001) [Pubmed]
  11. Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3. Tanaka, Y., Kato, J., Kohara, M., Galinski, M.S. Antiviral Res. (2006) [Pubmed]
  12. Post-translational protein modification in the endoplasmic reticulum. Demonstration of fatty acylase and deoxymannojirimycin-sensitive alpha-mannosidase activities. Rizzolo, L.J., Kornfeld, R. J. Biol. Chem. (1988) [Pubmed]
  13. Effects of tunicamycin and N-linked oligosaccharide-processing inhibitors on the morphology of cultured porcine thyroid cells. Giraud, A., Franc, J.L. Eur. J. Cell Biol. (1989) [Pubmed]
  14. Influence of N-glycan processing disruption on tyrosinase and melanin synthesis in HM3KO melanoma cells. Choi, H., Ahn, S., Chang, H., Cho, N.S., Joo, K., Lee, B.G., Chang, I., Hwang, J.S. Exp. Dermatol. (2007) [Pubmed]
  15. Pradimicin, a mannose-binding antibiotic, induced carbohydrate-mediated apoptosis in U937 cells. Oki, T., Yamazaki, Y., Furumai, T., Igarashi, Y. Biosci. Biotechnol. Biochem. (1997) [Pubmed]
  16. Carbohydrate synthesis inhibitors decrease interleukin 1-stimulated lymphocyte binding to endothelial cells. Renkonen, R., Ustinov, J. Eur. J. Immunol. (1991) [Pubmed]
  17. Inhibition of mannosidase in hybridomas yields monoclonal antibodies with greater capacity for carbohydrate labeling. Simonson, R.B., Ultee, M.E., Long, C.G., Gillette, R.W., McKearn, T.J., Rodwell, J.D. Clin. Chem. (1988) [Pubmed]
  18. Glucosidase trimming inhibitors preferentially perturb T cell activation induced by CD2 mAb. van Kemenade, F.J., Rotteveel, F.T., van den Broek, L.A., Baars, P.A., van Lier, R.A., Miedema, F. J. Leukoc. Biol. (1994) [Pubmed]
  19. Characterization of lipoprotein lipase activity, secretion, and degradation at different sites of post-translational processing in primary cultures of rat adipocytes. Simsolo, R.B., Ong, J.M., Kern, P.A. J. Lipid Res. (1992) [Pubmed]
  20. Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts. Sala, G., Dupré, T., Seta, N., Codogno, P., Ghidoni, R. Pediatr. Res. (2002) [Pubmed]
  21. Maturation of lipoprotein lipase. Expression of full catalytic activity requires glucose trimming but not translocation to the cis-Golgi compartment. Ben-Zeev, O., Doolittle, M.H., Davis, R.C., Elovson, J., Schotz, M.C. J. Biol. Chem. (1992) [Pubmed]
  22. Model for intracellular folding of the human immunodeficiency virus type 1 gp120. Fennie, C., Lasky, L.A. J. Virol. (1989) [Pubmed]
  23. Identification of a mammalian melanosomal matrix glycoprotein. Orlow, S.J., Zhou, B.K., Boissy, R.E., Pifko-Hirst, S. J. Invest. Dermatol. (1993) [Pubmed]
  24. Substrate specificity of the bovine and feline neutral alpha-mannosidases. De Gasperi, R., al Daher, S., Winchester, B.G., Warren, C.D. Biochem. J. (1992) [Pubmed]
  25. Role of calnexin, calreticulin, and endoplasmic reticulum mannosidase I in apolipoprotein(a) intracellular targeting. Wang, J., White, A.L. Biochemistry (2000) [Pubmed]
  26. Effect of inhibiting N-glycosylation or oligosaccharide processing on vasoactive intestinal peptide receptor binding activity and structure. el Battari, A., Forget, P., Fouchier, F., Pic, P. Biochem. J. (1991) [Pubmed]
  27. Interferon-gamma increases the expression of glycosylated CD95 in B-leukemic cells: an inducible model to study the role of glycosylation in CD95-signalling and trafficking. Dörrie, J., Sapala, K., Zunino, S.J. Cytokine (2002) [Pubmed]
  28. Effect of glycosidase inhibitors on the biosynthesis of alpha 2-plasmin inhibitor and antithrombin III in Hep G2 cells. Mori, K., Wada, Y., Mimuro, J., Matsuda, M., Yoshikuni, Y., Kimura, K., Sakata, Y. Biochim. Biophys. Acta (1994) [Pubmed]
  29. The relation between glycosylation and activity of guinea pig lipoprotein lipase. Semb, H., Olivecrona, T. J. Biol. Chem. (1989) [Pubmed]
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