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Chemical Compound Review

Sialyllactose     (2S,4S,5R,6R)-5-acetamido-2- [(2R,3S,4S,5R...

Synonyms: HMDB00825, AC1L3XJG, AR-1F5208, AKOS015916417, I14-50129, ...
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Disease relevance of Sialyllactose

  • Effects of strong electrolyte upon the activity of Clostridium perfringens sialidase toward sialyllactose and sialoglycolipids [1].
  • We report the effect of sialylation on cell surface on entry and the complex structure of DA virus, a persistent TMEV, and the receptor moiety mimic, sialyllactose, refined to a resolution of 3.0 A [2].
  • The viruses were assayed for their ability to bind the synthetic sialylglycopolymers 3'SL-PAA and 6'SLN-PAA, which contained, respectively, 3'-sialyllactose (the receptor determinant preferentially recognized by avian influenza viruses) and 6'-sialyl(N-acetyllactosamine) (the receptor determinant for human viruses) [3].
  • Gliding motility of Mycoplasma mobile can occur by repeated binding to N-acetylneuraminyllactose (sialyllactose) fixed on solid surfaces [4].
  • Molecular modeling studies based on the crystal structure of the influenza A virus hemagglutinin complexed with sialyllactose suggest a steric hindrance of hemagglutinin binding to aliphatically elongated N-acyl groups [5].

High impact information on Sialyllactose

  • Crystal structure of the N-terminal domain of sialoadhesin in complex with 3' sialyllactose at 1.85 A resolution [6].
  • This study aimed to determine the safety and efficacy of 3'-sialyllactose sodium salt (3'SL), an oligosaccharide that occurs naturally in human and bovine milk and that can inhibit the adhesion of H. pylori to human epithelial cells in vitro [7].
  • The structures of BoNT/B and its complex with sialyllactose provide a detailed description of the active site and a model for interactions between the toxin and its cell surface receptor [8].
  • GAS epitope on these nucleated cells, (1) like that present on RBC, is abolished by sialidase, unaffected by proteases, and inhibited by sialyllactose; and (2) is overlapping and/or proximal to that recognized by anti-sLe(x) MoAb, CSLEX-1, and KM-93 [9].
  • This additional CD24 MoAb reactivity on T lymphocytes was, in common with that observed on granulocytes (CD24 protein+), specifically inhibited by the presence of both sialyllactose and mucin [10].

Chemical compound and disease context of Sialyllactose

  • The resulting styrene derivative substituted with sialyllactose via an amide linkage was polymerized with ammonium peroxodisulfate and N,N,N',N-tetramethylethylenediamine in water at 30 degrees C. The interaction of the glycopolymer with influenza A and B viruses was investigated by three different methods [11].
  • When lactose was used as acceptor, again lower enzyme activity in the tumor cells in comparison with that in liver was established, but in liver and in hepatoma cells the predominant 14C-labelled product of the sialyltransferase assay was alpha (2-6) sialyllactose isomer [12].
  • The subcellular distribution of sialidase in rat hepatoma induced by 3'-methyl-4-dimethylaminoazobenzene was studied by using sialyllactose as a substrate in the pH range of 4.0-7 [13].

Biological context of Sialyllactose


Anatomical context of Sialyllactose

  • The cold agglutinin activity of MAT can be inhibited by sialyllactose or treatment of erythrocytes with neuraminidase but not papain [19].
  • As a specific ligand for the sialyllactose (SL)-binding proteins on granulosa cells, we used a radioiodinated multivalent SL-linked albumin (Alb-(SL)17) [14].
  • Incubating virus with soluble sialyllactose blocked fusion to both ganglioside-free and ganglioside-containing planar membranes [20].
  • The large-scale preparation of pure sialyllactose isomers from bovine colostrum is achieved using an improved ion-exchange separation on Dowex 1-X2 (less than 400 mesh) employing isomolar elution at 20 mM for monosialyloligosaccharides and 200 mM for disialyllactose [21].
  • Antisera specific for LS-tetrasaccharide c and 3'-sialyllactose (NeuAc alpha 2-3Gal beta 1-4Glc) identify their corresponding 3H-labeled haptens released from the major meconium gangliosides 6'-LM1 and GM3, respectively [22].

Associations of Sialyllactose with other chemical compounds

  • The intact SBP could bind various gangliosides, and the binding was sialidase-sensitive and inhibited by sialyllactose, thus indicating that it is the sialic acid-binding protein [23].
  • Furthermore, treatment of CD45 proteins with O-glycanase or neuraminidase resulted in the loss of both CD45R0 and CD45RB epitopes, although reactivity of the anti-CD45R0 and anti-CD45RB mAb was not affected by mAb preincubation with either sialic acids or sialyllactose in solution [24].
  • HepIII is chain elongated at O-2 by either a beta-D-Glcp residue (major), lactose or sialyllactose (minor, i.e. alpha-Neu5Ac-(2-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp), where a third minor acetylation site was identified at the glucose residue [25].
  • In contrast to the intralysosomal sialidase, the sialidase partially purified from rat liver cytosol by (NH4)2SO4 fractionation followed by chromatography on DEAE-cellulose and CM-cellulose hydrolyzed fetuin and orosomucoid to the extent about half that for sialyllactose [26].
  • Results indicated that 3'-sialyllactose and lactose were efficient acceptors of sulfation, whereas 6'-sialyllactose and 6'-sialyllactosamine were poor substrates for this sulfotransferase [27].

Gene context of Sialyllactose

  • ST8Sia VI also exhibited activity toward oligosaccharides such as sialyllactose and sialyllactosamine, and the structure of the minimal acceptor substrate for ST8Sia VI was determined as the NeuAcalpha2,3(6)Gal sequence [28].
  • 5. The enzyme also efficiently hydrolyzed GD3, GD1a, GD1b and GM3 whereas sialyllactose, 4MU-NeuAc, GM1 and GM2 were poor substrates, and it had no activity against sialylated glycoproteins such as fetuin, transferrin and orosomucoid [29].
  • However, results for the lpsA mutant indicate that sialyllactose extends from HepI as well, a molecular environment for sialyllactose in H. influenzae that has not been reported previously [30].
  • Structural studies of the parainfluenza virus 5 hemagglutinin-neuraminidase tetramer in complex with its receptor, sialyllactose [31].
  • The optimum pH was 6.5 for sialyllactose and 6.0 for orosomucoid and mixed brain gangliosides [32].

Analytical, diagnostic and therapeutic context of Sialyllactose

  • The three-dimensional structure of the complex between M. amurensis leukoagglutinin and sialyllactose has been determined at 2.75-A resolution using x-ray crystallography [33].
  • PMP sialyllactose, when ionized by ESI/MALDI, produced a mixture of [M + H]+, [M + Na]+, [M - H + 2Na]+ ions in the positive mode and [M - H]-, [M + Na - 2H]- ions in the negative mode [34].
  • After centrifugation, the activities with sialyllactose and fetuin were largely recovered in the supernatant, demonstrating that they were originally in the intralysosomal space [26].
  • The enzyme was maximally active at pH 4.7 with sialyllactose as substrate and had a minimum relative molecular mass of 60 000 +/- 5000 by gel filtration; it hydrolyzed a variety of sialooligosaccharides , those containing (alpha 2----3)sialyl linkages being better substrates than those with (alpha 2----6)sialyl linkages [26].
  • In Sda serological tests the product formed with 3'-sialyl-N-acetyllactosamine was highly active whereas that formed with 3'-sialyllactose had only weak activity [35].


  1. Effects of strong electrolyte upon the activity of Clostridium perfringens sialidase toward sialyllactose and sialoglycolipids. Barton, N.W., Lipovac, V., Rosenberg, A. J. Biol. Chem. (1975) [Pubmed]
  2. Sialylation of the host receptor may modulate entry of demyelinating persistent Theiler's virus. Zhou, L., Luo, Y., Wu, Y., Tsao, J., Luo, M. J. Virol. (2000) [Pubmed]
  3. Early alterations of the receptor-binding properties of H1, H2, and H3 avian influenza virus hemagglutinins after their introduction into mammals. Matrosovich, M., Tuzikov, A., Bovin, N., Gambaryan, A., Klimov, A., Castrucci, M.R., Donatelli, I., Kawaoka, Y. J. Virol. (2000) [Pubmed]
  4. Gliding motility of Mycoplasma mobile can occur by repeated binding to N-acetylneuraminyllactose (sialyllactose) fixed on solid surfaces. Nagai, R., Miyata, M. J. Bacteriol. (2006) [Pubmed]
  5. Elongation of the N-acyl side chain of sialic acids in MDCK II cells inhibits influenza A virus infection. Keppler, O.T., Herrmann, M., von der Lieth, C.W., Stehling, P., Reutter, W., Pawlita, M. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  6. Crystal structure of the N-terminal domain of sialoadhesin in complex with 3' sialyllactose at 1.85 A resolution. May, A.P., Robinson, R.C., Vinson, M., Crocker, P.R., Jones, E.Y. Mol. Cell (1998) [Pubmed]
  7. Treatment of Helicobacter pylori infection in rhesus monkeys using a novel antiadhesion compound. Mysore, J.V., Wigginton, T., Simon, P.M., Zopf, D., Heman-Ackah, L.M., Dubois, A. Gastroenterology (1999) [Pubmed]
  8. Structural analysis of the catalytic and binding sites of Clostridium botulinum neurotoxin B. Swaminathan, S., Eswaramoorthy, S. Nat. Struct. Biol. (2000) [Pubmed]
  9. Anti-Sia-lb (anti-Gd) cold agglutinins bind the domain NeuNAc alpha2-3Gal in sialyl Lewis(x), sialyl Lewis(a), and related carbohydrates on nucleated cells and in soluble cancer-associated mucins. Gallart, T., Roelcke, D., Blay, M., Pereira, A., Martínez, A., Massó, O., Viñas, O., Cid, M., Esparza, J., Molina, R., Barceló, J. Blood (1997) [Pubmed]
  10. Human T lymphocytes and hematopoietic cell lines express CD24-associated carbohydrate epitopes in the absence of CD24 mRNA or protein. Williams, L.A., Hock, B.D., Hart, D.N. Blood (1996) [Pubmed]
  11. Simple synthesis of sialyllactose-carrying polystyrene and its binding with influenza virus. Tsuchida, A., Kobayashi, K., Matsubara, N., Muramatsu, T., Suzuki, T., Suzuki, Y. Glycoconj. J. (1998) [Pubmed]
  12. Activity and characterization of sialyltransferase from serum of normal rats, of rats bearing Zajdela ascitic hepatoma, in normal host liver and in Zajdela hepatoma cells. Ivanov, D.G., Karaivanova, V.K., Ivanov, S.X., Chelibonova-Lorer, H. Neoplasma (1996) [Pubmed]
  13. Sialidase of rat hepatomas: qualitative and quantitative comparison with rat liver sialidase. Miyagi, T., Goto, T., Tsuiki, S. Gann = Gan. (1984) [Pubmed]
  14. Sialyllactose-mediated cell interaction during granulosa cell differentiation. Identification of its binding proteins. Hattori, M., Horiuchi, R., Hosaka, K., Hayashi, H., Kojima, I. J. Biol. Chem. (1995) [Pubmed]
  15. Reovirus binding to cell surface sialic acid potentiates virus-induced apoptosis. Connolly, J.L., Barton, E.S., Dermody, T.S. J. Virol. (2001) [Pubmed]
  16. Mutagenesis of the conserved active-site tyrosine changes a retaining sialidase into an inverting sialidase. Watson, J.N., Dookhun, V., Borgford, T.J., Bennet, A.J. Biochemistry (2003) [Pubmed]
  17. Inhibition of Helicobacter pylori binding to gastrointestinal epithelial cells by sialic acid-containing oligosaccharides. Simon, P.M., Goode, P.L., Mobasseri, A., Zopf, D. Infect. Immun. (1997) [Pubmed]
  18. Increased urinary excretion of free N-acetylneuraminic acid in thirteen patients with Salla disease. Renlund, M., Chester, M.A., Lundblad, A., Aula, P., Raivio, K.O., Autio, S., Koskela, S.L. Eur. J. Biochem. (1979) [Pubmed]
  19. The molecular mechanism of cryoprecipitation and cold agglutination of an IgM lambda Waldenström macroglobulin with anti-Gd specificity: sedimentation analysis and localization of interacting sites. Weber, R.J., Clem, L.W. J. Immunol. (1981) [Pubmed]
  20. The role of N-acetylneuraminic (sialic) acid in the pH dependence of influenza virion fusion with planar phospholipid membranes. Niles, W.D., Cohen, F.S. J. Gen. Physiol. (1991) [Pubmed]
  21. New chromatographic system for the rapid analysis and preparation of colostrum sialyloligosaccharides. Veh, R.W., Michalski, J.C., Corfield, A.P., Sander-Wewer, M., Gies, D., Schauer, R. J. Chromatogr. (1981) [Pubmed]
  22. A new ganglioside in human meconium detected by antiserum against the human milk sialyloligosaccharide, LS-tetrasaccharide b. Prieto, P.A., Smith, D.F. Arch. Biochem. Biophys. (1985) [Pubmed]
  23. Identification of the sea urchin 350-kDa sperm-binding protein as a new sialic acid-binding lectin that belongs to the heat shock protein 110 family: implication of its binding to gangliosides in sperm lipid rafts in fertilization. Maehashi, E., Sato, C., Ohta, K., Harada, Y., Matsuda, T., Hirohashi, N., Lennarz, W.J., Kitajima, K. J. Biol. Chem. (2003) [Pubmed]
  24. Glycosylation of CD45: carbohydrate composition and its role in acquisition of CD45R0 and CD45RB T cell maturation-related antigen specificities during biosynthesis. Pulido, R., Sánchez-Madrid, F. Eur. J. Immunol. (1990) [Pubmed]
  25. Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 1003. Månsson, M., Hood, D.W., Li, J., Richards, J.C., Moxon, E.R., Schweda, E.K. Eur. J. Biochem. (2002) [Pubmed]
  26. Rat-liver lysosomal sialidase. Solubilization, substrate specificity and comparison with the cytosolic sialidase. Miyagi, T., Tsuiki, S. Eur. J. Biochem. (1984) [Pubmed]
  27. Isolation and characterization from porcine serum of a soluble sulfotransferase responsible for 6-O-sulfation of the galactose residue in 2'-fucosyllactose: implications in the synthesis of the ligand for L-selectin. Huynh, Q.K., Shailubhai, K., Boddupalli, H., Yu, H.H., Broschat, K.O., Jacob, G.S. Glycoconj. J. (1999) [Pubmed]
  28. Molecular cloning and expression of a sixth type of alpha 2,8-sialyltransferase (ST8Sia VI) that sialylates O-glycans. Takashima, S., Ishida, H.K., Inazu, T., Ando, T., Ishida, H., Kiso, M., Tsuji, S., Tsujimoto, M. J. Biol. Chem. (2002) [Pubmed]
  29. Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli. Ha, K.T., Lee, Y.C., Cho, S.H., Kim, J.K., Kim, C.H. Mol. Cells (2004) [Pubmed]
  30. An alternate pattern for globoside oligosaccharide expression in Haemophilus influenzae lipopolysaccharide: structural diversity in nontypeable strain 1124. Yildirim, H.H., Li, J., Richards, J.C., Hood, D.W., Moxon, E.R., Schweda, E.K. Biochemistry (2005) [Pubmed]
  31. Structural studies of the parainfluenza virus 5 hemagglutinin-neuraminidase tetramer in complex with its receptor, sialyllactose. Yuan, P., Thompson, T.B., Wurzburg, B.A., Paterson, R.G., Lamb, R.A., Jardetzky, T.S. Structure (Camb.) (2005) [Pubmed]
  32. Purification and characterization of cytosolic sialidase from rat liver. Miyagi, T., Tsuiki, S. J. Biol. Chem. (1985) [Pubmed]
  33. An unusual carbohydrate binding site revealed by the structures of two Maackia amurensis lectins complexed with sialic acid-containing oligosaccharides. Imberty, A., Gautier, C., Lescar, J., Pérez, S., Wyns, L., Loris, R. J. Biol. Chem. (2000) [Pubmed]
  34. Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry. Lattová, E., Snovida, S., Perreault, H., Krokhin, O. J. Am. Soc. Mass Spectrom. (2005) [Pubmed]
  35. Enzymic synthesis, chemical characterisation and Sda activity of GalNAc beta 1-4[NeuAc alpha 2-3]Gal beta 1-4GlcNAc and GalNAc beta 1-4[NeuAc alpha 2-3]Gal beta 1-4Glc. Soh, C.P., Donald, A.S., Feeney, J., Morgan, W.T., Watkins, W.M. Glycoconj. J. (1989) [Pubmed]
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