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Chemical Compound Review

galactose     (3R,4S,5R,6R)-6- (hydroxymethyl)oxane-2,3,4...

Synonyms: D-galactose, dl-Galactose, D(+)-Galactose, D-()-Galactose, SureCN38935, ...
 
 
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Disease relevance of galactopyranoside

  • Four of six human monoclonal IgM proteins were found to react best with Klebsiella polysaccharides containing 3,4py beta DGal (pyruvic acetalated D-galactopyranose), one with Klebsiella polysaccharides with 4,6pyDGlc; the sixth is uncharacterized [1].
  • In contrast, each strain was recognized by the Gal- and GalNAc-reactive lectins of Actinomyces spp., but only strains 38 and 34 were recognized by GalNAc-sensitive lectins of other streptococci [2].
  • The fei genes were found to be located close to the galactose operon (gal) between the position 17 and 21 of the E. coli chromosomal linkage map [3].
 

High impact information on galactopyranoside

  • This Gal/GalNAc-inhibitable lectin has been shown previously to mediate adherence of E. histolytica to mammalian epithelial cells [4].
  • The PAP cDNA was placed under control of the galactose-inducible GAL1 promoter and transformed into Saccharomyces cerevisiae [5].
  • GT-Ko mice tolerized to Gal-expressing C3H hearts and IAB plus transient anti-CD40L therapy were challenged with pig kidney membranes that express high levels of Gal [6].
  • In this study, we take advantage of the ability of galactosyltransferase-deficient knockout (GT-Ko) mice to respond to the carbohydrate epitope, galactose-alpha1,3-galactose (Gal), to investigate whether IAB plus transient anti-CD40L therapy directly tolerize B cell responses [6].
  • Cell growth is inhibited when PAP cDNA is expressed in the yeast Saccharomyces cerevisiae under the control of the galactose-inducible GAL1 promoter [7].
 

Biological context of galactopyranoside

 

Anatomical context of galactopyranoside

 

Associations of galactopyranoside with other chemical compounds

  • Of the 35 amino acids in the TM1O region, only 12 differ between Ga12 and Hxt2, indicating that these 12 amino acids include the critical residue(s) responsible for the differential recognition of galactose and glucose in these transporters [13].
  • The higher binding affinity of GalNAc over Gal to SBA is due to additional hydrophobic interactions with Tyr107 rather than a hydrogen bond between N-acetamide group of the sugar and the side chain of Asp88 as suggested from X-ray crystal structure studies [14].
  • The hydrogen bonding scheme, predicted from the homology model, shows that the invariant residues i.e. Asp, Gly, Asn, and aromatic residues (Phe) found in all other legume lectins, bind Gal, slightly in a different way than reported in X-ray structure of SBA-pentasaccharide complex [14].
 

Gene context of galactopyranoside

References

  1. Immunochemical studies on human monoclonal macroglobulins with specificities for 3,4-pyruvylated D-galactose and 4,6-pyruvylated D-glucose. Rao, A.S., Liao, J., Kabat, E.A., Osserman, E.F., Harboe, M., Nimmich, W. J. Biol. Chem. (1984) [Pubmed]
  2. The cell wall polysaccharide of Streptococcus gordonii 38: structure and immunochemical comparison with the receptor polysaccharides of Streptococcus oralis 34 and Streptococcus mitis J22. Reddy, G.P., Abeygunawardana, C., Bush, C.A., Cisar, J.O. Glycobiology (1994) [Pubmed]
  3. Chromosomal mapping of genes encoding mannose-sensitive (type I) and mannose-resistant F8 (P) fimbriae of Escherichia coli O18:K5:H5. Krallmann-Wenzel, U., Ott, M., Hacker, J., Schmidt, G. FEMS Microbiol. Lett. (1989) [Pubmed]
  4. Identification of a Gal/GalNAc lectin in the protozoan Hartmannella vermiformis as a potential receptor for attachment and invasion by the Legionnaires' disease bacterium. Venkataraman, C., Haack, B.J., Bondada, S., Abu Kwaik, Y. J. Exp. Med. (1997) [Pubmed]
  5. Isolation and characterization of pokeweed antiviral protein mutations in Saccharomyces cerevisiae: identification of residues important for toxicity. Hur, Y., Hwang, D.J., Zoubenko, O., Coetzer, C., Uckun, F.M., Tumer, N.E. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  6. Intact active bone transplantation synergizes with anti-CD40 ligand therapy to induce B cell tolerance. Yin, D., Ma, L., Varghese, A., Shen, J., Chong, A.S. J. Immunol. (2002) [Pubmed]
  7. Pokeweed antiviral protein regulates the stability of its own mRNA by a mechanism that requires depurination but can be separated from depurination of the alpha-sarcin/ricin loop of rRNA. Parikh, B.A., Coetzer, C., Tumer, N.E. J. Biol. Chem. (2002) [Pubmed]
  8. Protein-ligand energetics assessed using deoxy and fluorodeoxy sugars in equilibrium binding and high resolution crystallographic studies. Vermersch, P.S., Tesmer, J.J., Quiocho, F.A. J. Mol. Biol. (1992) [Pubmed]
  9. Exocellular components of Paracoccidioides brasiliensis: identification of a specific antigen. Puccia, R., Schenkman, S., Gorin, P.A., Travassos, L.R. Infect. Immun. (1986) [Pubmed]
  10. Improved high-performance liquid chromatographic method to estimate aminosugars and its application to glycosaminoglycan determination in plasma and serum. Campo, G.M., Campo, S., Ferlazzo, A.M., Vinci, R., Calatroni, A. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]
  11. Activation of procollagenase IV by cytochalasin D and concanavalin A in cultured rat mesangial cells: linkage to cytoskeletal reorganization. Allenberg, M., Weinstein, T., Li, I., Silverman, M. J. Am. Soc. Nephrol. (1994) [Pubmed]
  12. Detection of terminal N-linked N-acetylglucosamine residues in the Golgi apparatus using galactosyltransferase and endoglucosaminidase F/peptide N-glycosidase F: adaptation of a biochemical approach to electron microscopy. Lucocq, J.M., Berger, E.G., Roth, J. J. Histochem. Cytochem. (1987) [Pubmed]
  13. Transmembrane segment 10 is important for substrate recognition in Ga12 and Hxt2 sugar transporters in the yeast Saccharomyces cerevisiae. Kasahara, M., Shimoda, E., Maeda, M. FEBS Lett. (1996) [Pubmed]
  14. Three dimensional structure of the soybean agglutinin Gal/GalNAc complexes by homology modeling. Rao, V.S., Lam, K., Qasba, P.K. J. Biomol. Struct. Dyn. (1998) [Pubmed]
  15. Receptor-directed contrast agents for MR imaging: preclinical evaluation with affinity assays. Reimer, P., Weissleder, R., Wittenberg, J., Brady, T.J. Radiology. (1992) [Pubmed]
 
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