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Chemical Compound Review

AGN-PC-00HZ5Q     N-[2,4-dihydroxy-6- (hydroxymethyl)-5-[3,4...

Synonyms: SureCN13211438, AR-1C8344, AKOS015919228, AC1L18T1, AC1Q5O3C, ...
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Disease relevance of N-acetyllactosamine


High impact information on N-acetyllactosamine


Chemical compound and disease context of N-acetyllactosamine

  • Embryonal carcinoma (EC) cells possess a complex cell surface glycoconjugate called lactosaminoglycan, whose core structure is composed of repeating N-acetyllactosamine (Gal leads to GlcNAc) disaccharides [9].
  • In functional assays alpha 2,3-ST and alpha 1,3- or 1,4-FT activities were observed in adenocarcinoma cell lysates to exogenous N-acetyllactosamine and lacto-N-biose acceptors and to their sialylated derivatives, leading to the synthesis of the sialyl-N-acetyllactosamine and s(Lex) or the sialyllacto-N-biose and s(Lea), respectively [10].
  • Glucosylated N-acetyllactosamine O-antigen chain in the lipopolysaccharide from Helicobacter pylori strain UA861 [11].
  • The major lipooligosaccharides of the sexually transmitted pathogen Haemophilus ducreyi 35000 have been previously found to terminate in N-acetyllactosamine and sialyl-N-acetyllactosamine, Neu5Ac alpha 2-->3Gal beta 1-->4GlcNAc (W. Melaugh, N. J. Phillips, A. A. Campagnari, M. V. Tullius, and B. W. Gibson, Biochemistry 33: 13070-13078, 1994) [12].

Biological context of N-acetyllactosamine


Anatomical context of N-acetyllactosamine


Associations of N-acetyllactosamine with other chemical compounds


Gene context of N-acetyllactosamine

  • Removal of polylactosamine chains by endo-beta D-galactosidase digestion significantly reduced the electrophoretic mobility of the immunoreactive bands, suggesting that HLA-G, unlike class Ib molecules studied to date, carries N-acetyllactosamine units [28].
  • The HNK-1 glycan synthesis is initiated by the addition of beta1,3-linked GlcA to N-acetyllactosamine followed by sulfation of the C-3 position of GlcA [29].
  • The amounts of T antigen and N-acetyllactosamine oligosaccharides on MUC5B increased during the first half of the cycle, peaked at midcycle, and dramatically dropped at the end of the cycle [30].
  • Like mammalian prototype galectin-1, Drgal1-L2 preferentially binds to N-acetyllactosamine [31].
  • In addition, AQN-3 binds preferentially to glycoproteins with either a linear or tri- and tetraantennary carbohydrates than to those containing diantennary N-acetyllactosamine structures [32].

Analytical, diagnostic and therapeutic context of N-acetyllactosamine


  1. Reduction of metastatic properties of BL6 melanoma cells expressing terminal fucose(alpha)1-2-galactose after alpha1,2-fucosyltransferase cDNA transfection. Gorelik, E., Xu, F., Henion, T., Anaraki, F., Galili, U. Cancer Res. (1997) [Pubmed]
  2. Haemophilus ducreyi produces a novel sialyltransferase. Identification of the sialyltransferase gene and construction of mutants deficient in the production of the sialic acid-containing glycoform of the lipooligosaccharide. Bozue, J.A., Tullius, M.V., Wang, J., Gibson, B.W., Munson, R.S. J. Biol. Chem. (1999) [Pubmed]
  3. Neisseria gonorrhoeae that infect men have lipooligosaccharides with terminal N-acetyllactosamine repeats. John, C.M., Schneider, H., Griffiss, J.M. J. Biol. Chem. (1999) [Pubmed]
  4. Ovarian cancer alpha 1,3-L-fucosyltransferase. Differentiation of distinct catalytic species with the unique substrate, 3'-sulfo-N-acetyllactosamine in conjunction with other synthetic acceptors. Chandrasekaran, E.V., Jain, R.K., Matta, K.L. J. Biol. Chem. (1992) [Pubmed]
  5. Lupus IgG VH4.34 antibodies bind to a 220-kDa glycoform of CD45/B220 on the surface of human B lymphocytes. Cappione, A.J., Pugh-Bernard, A.E., Anolik, J.H., Sanz, I. J. Immunol. (2004) [Pubmed]
  6. Lipooligosaccharides (LOS) of Neisseria gonorrhoeae and Neisseria meningitidis have components that are immunochemically similar to precursors of human blood group antigens. Carbohydrate sequence specificity of the mouse monoclonal antibodies that recognize crossreacting antigens on LOS and human erythrocytes. Mandrell, R.E., Griffiss, J.M., Macher, B.A. J. Exp. Med. (1988) [Pubmed]
  7. Crosslinking of mammalian lectin (galectin-1) by complex biantennary saccharides. Bourne, Y., Bolgiano, B., Liao, D.I., Strecker, G., Cantau, P., Herzberg, O., Feizi, T., Cambillau, C. Nat. Struct. Biol. (1994) [Pubmed]
  8. Structure of S-lectin, a developmentally regulated vertebrate beta-galactoside-binding protein. Liao, D.I., Kapadia, G., Ahmed, H., Vasta, G.R., Herzberg, O. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Embryonal carcinoma cell adhesion: the role of surface galactosyltransferase and its 90K lactosaminoglycan substrate. Shur, B.D. Dev. Biol. (1983) [Pubmed]
  10. Expression and function of alpha 2,3-sialyl- and alpha 1,3/1,4-fucosyltransferases in colon adenocarcinoma cell lines: role in synthesis of E-selectin counter-receptors. Majuri, M.L., Niemelä, R., Tiisala, S., Renkonen, O., Renkonen, R. Int. J. Cancer (1995) [Pubmed]
  11. Glucosylated N-acetyllactosamine O-antigen chain in the lipopolysaccharide from Helicobacter pylori strain UA861. Monteiro, M.A., Rasko, D., Taylor, D.E., Perry, M.B. Glycobiology (1998) [Pubmed]
  12. The lipooligosaccharides of Haemophilus ducreyi are highly sialylated. Melaugh, W., Campagnari, A.A., Gibson, B.W. J. Bacteriol. (1996) [Pubmed]
  13. Regulation of glycosylation. The influence of protein structure on N-linked oligosaccharide processing. Hubbard, S.C. J. Biol. Chem. (1988) [Pubmed]
  14. Two lectins from the marine sponge Halichondria okadai. An N-acetyl-sugar-specific lectin (HOL-I) and an N-acetyllactosamine-specific lectin (HOL-II). Kawagishi, H., Yamawaki, M., Isobe, S., Usui, T., Kimura, A., Chiba, S. J. Biol. Chem. (1994) [Pubmed]
  15. Molecular cloning of a human fucosyltransferase gene that determines expression of the Lewis x and VIM-2 epitopes but not ELAM-1-dependent cell adhesion. Lowe, J.B., Kukowska-Latallo, J.F., Nair, R.P., Larsen, R.D., Marks, R.M., Macher, B.A., Kelly, R.J., Ernst, L.K. J. Biol. Chem. (1991) [Pubmed]
  16. Characterization of oligosaccharide ligands expressed on SW1116 cells recognized by mannan-binding protein. A highly fucosylated polylactosamine type N-glycan. Terada, M., Khoo, K.H., Inoue, R., Chen, C.I., Yamada, K., Sakaguchi, H., Kadowaki, N., Ma, B.Y., Oka, S., Kawasaki, T., Kawasaki, N. J. Biol. Chem. (2005) [Pubmed]
  17. Novel binding epitope for Helicobacter pylori found in neolacto carbohydrate chains: structure and cross-binding properties. Miller-Podraza, H., Lanne, B., Angström, J., Teneberg, S., Milh, M.A., Jovall, P.A., Karlsson, H., Karlsson, K.A. J. Biol. Chem. (2005) [Pubmed]
  18. Alterations of cell surface carbohydrates and inhibition of metastatic property of murine melanomas by alpha 1,3 galactosyltransferase gene transfection. Gorelik, E., Duty, L., Anaraki, F., Galili, U. Cancer Res. (1995) [Pubmed]
  19. Branch specificity of bovine colostrum CMP-sialic acid: Gal beta 1----4GlcNAc-R alpha 2----6-sialyltransferase. Sialylation of bi-, tri-, and tetraantennary oligosaccharides and glycopeptides of the N-acetyllactosamine type. Joziasse, D.H., Schiphorst, W.E., Van den Eijnden, D.H., Van Kuik, J.A., Van Halbeek, H., Vliegenthart, J.F. J. Biol. Chem. (1987) [Pubmed]
  20. The distribution of repeating [Gal beta 1,4GlcNAc beta 1,3] sequences in asparagine-linked oligosaccharides of the mouse lymphoma cell lines BW5147 and PHAR 2.1. Cummings, R.D., Kornfeld, S. J. Biol. Chem. (1984) [Pubmed]
  21. Biosynthesis of blood group i-active polylactosaminoglycans. Partial purification and properties of an UDP-GlcNAc:N-acetyllactosaminide beta 1----3-N-acetylglucosaminyltransferase from Novikoff tumor cell ascites fluid. van den Eijnden, D.H., Koenderman, A.H., Schiphorst, W.E. J. Biol. Chem. (1988) [Pubmed]
  22. Molecular cloning and expression of a novel human beta-Gal-3-O-sulfotransferase that acts preferentially on N-acetyllactosamine in N- and O-glycans. Suzuki, A., Hiraoka, N., Suzuki, M., Angata, K., Misra, A.K., McAuliffe, J., Hindsgaul, O., Fukuda, M. J. Biol. Chem. (2001) [Pubmed]
  23. Mitogenic leukoagglutinin from Phaseolus vulgaris binds to a pentasaccharide unit in N-acetyllactosamine-type glycoprotein glycans. Hammarström, S., Hammarström, M.L., Sundblad, G., Arnarp, J., Lönngren, J. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  24. Accumulation of a blood group antigen precursor in oral premalignant lesions. Dabelsteen, E., Vedtofte, P., Hakomori, S., Young, W.W. Cancer Res. (1983) [Pubmed]
  25. X-ray crystal structure of the human galectin-3 carbohydrate recognition domain at 2.1-A resolution. Seetharaman, J., Kanigsberg, A., Slaaby, R., Leffler, H., Barondes, S.H., Rini, J.M. J. Biol. Chem. (1998) [Pubmed]
  26. Binding characteristics of galactoside-binding lectin (galaptin) from human spleen. Lee, R.T., Ichikawa, Y., Allen, H.J., Lee, Y.C. J. Biol. Chem. (1990) [Pubmed]
  27. Structures of the complex glycans found on the beta-subunit of (Na,K)-ATPase. Treuheit, M.J., Costello, C.E., Kirley, T.L. J. Biol. Chem. (1993) [Pubmed]
  28. HLA-G isoforms produced by placental cytotrophoblasts and found in amniotic fluid are due to unusual glycosylation. McMaster, M., Zhou, Y., Shorter, S., Kapasi, K., Geraghty, D., Lim, K.H., Fisher, S. J. Immunol. (1998) [Pubmed]
  29. Biosynthesis of HNK-1 glycans on O-linked oligosaccharides attached to the neural cell adhesion molecule (NCAM): the requirement for core 2 beta 1,6-N-acetylglucosaminyltransferase and the muscle-specific domain in NCAM. Ong, E., Suzuki, M., Belot, F., Yeh, J.C., Franceschini, I., Angata, K., Hindsgaul, O., Fukuda, M. J. Biol. Chem. (2002) [Pubmed]
  30. Variation in the amount of T antigen and N-acetyllactosamine oligosaccharides in human cervical mucus secretions with the menstrual cycle. Argüeso, P., Spurr-Michaud, S., Tisdale, A., Gipson, I.K. J. Clin. Endocrinol. Metab. (2002) [Pubmed]
  31. Biochemical and molecular characterization of galectins from zebrafish (Danio rerio): notochord-specific expression of a prototype galectin during early embryogenesis. Ahmed, H., Du, S.J., O'Leary, N., Vasta, G.R. Glycobiology (2004) [Pubmed]
  32. Boar spermadhesins AQN-1 and AQN-3: oligosaccharide and zona pellucida binding characteristics. Calvete, J.J., Carrera, E., Sanz, L., Töpfer-Petersen, E. Biol. Chem. (1996) [Pubmed]
  33. Survival of recombinant erythropoietin in the circulation: the role of carbohydrates. Fukuda, M.N., Sasaki, H., Lopez, L., Fukuda, M. Blood (1989) [Pubmed]
  34. Characterization of the carbohydrate binding specificity of the leukoagglutinating lectin from Maackia amurensis. Comparison with other sialic acid-specific lectins. Knibbs, R.N., Goldstein, I.J., Ratcliffe, R.M., Shibuya, N. J. Biol. Chem. (1991) [Pubmed]
  35. Removal of terminal alpha-galactosyl residues from xenogeneic porcine endothelial cells. Decrease in complement-mediated cytotoxicity but persistence of IgG1-mediated antibody-dependent cell-mediated cytotoxicity. Watier, H., Guillaumin, J.M., Piller, F., Lacord, M., Thibault, G., Lebranchu, Y., Monsigny, M., Bardos, P. Transplantation (1996) [Pubmed]
  36. Increase of sialylated tetraantennary sugar chains in parallel to the higher lung-colonizing abilities of mouse melanoma clones. Yamamura, K., Takasaki, S., Ichihashi, M., Mishima, Y., Kobata, A. J. Invest. Dermatol. (1991) [Pubmed]
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