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Chemical Compound Review

NSC-2028     2,3,4,5-tetrahydroxy-6- [3,4,5-trihydroxy-6...

Synonyms: G5643_SIGMA, M7788_SIGMA, NSC2028, AR-1H2459, AC1L57Y0, ...
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Disease relevance of melibiose


High impact information on melibiose


Chemical compound and disease context of melibiose


Biological context of melibiose

  • Yeast transformed with GAL4-bearing plasmid become constitutive for expression of the galactose/melibiose genes, even in normally repressing (glucose) medium [9].
  • These observations suggested that expression of the melibiose operon in W3133 is also temperature-sensitive [15].
  • The cloned alkaliphile gene restored to NM81 the ability to grow at pH 7.5 in the presence of 0.6 M NaCl and on 100 mM Li+ in the presence of melibiose, and concomitantly led to an increase in the membrane associated Na+/H+ antiport activity [16].
  • We cloned the mutated melB gene that encodes the melibiose carrier, determined the nucleotide sequences, and identified replaced nucleotides [2].
  • The proteoliposomes exhibited counterflow activity, as well as membrane potential and sodium gradient-driven melibiose accumulation [17].

Anatomical context of melibiose

  • Lectin from the embryos and oocytes was purified by affinity chromatography on a column derivatized with melibiose [18].
  • By use of techniques described recently for lac permease [Roepe, P.D., & Kaback, H.R. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 6087], the melibiose permease from Escherichia coli, another polytopic integral plasma membrane protein, has been purified in a metastable soluble form after overexpression of the melB gene via the T7 RNA polymerase system [19].
  • The synthetic free alpha-galactosyl epitope (Gal alpha1-3Gal beta1-4GlcNAc) was found to be 300-fold more effective than melibiose or alpha-methyl galactoside in inhibiting anti-Gal binding to porcine endothelial cells, and to prevent >90% of the antibody binding at a concentration of 1 mM [20].
  • Melibiose decreased TEER dose-dependently in the jejunum and cecum, but not in the ileum and colon [21].
  • The addition of 1-100 mmol/L melibiose, difructose anhydride (DFA)III, or DFAIV to the mucosal medium increased the net Ca absorption and LY permeability dose-dependently in the jejunum, ileum, cecum and colon preparations [21].

Associations of melibiose with other chemical compounds


Gene context of melibiose


Analytical, diagnostic and therapeutic context of melibiose


  1. Projection structure at 8 A resolution of the melibiose permease, an Na-sugar co-transporter from Escherichia coli. Hacksell, I., Rigaud, J.L., Purhonen, P., Pourcher, T., Hebert, H., Leblanc, G. EMBO J. (2002) [Pubmed]
  2. Resistance of the melibiose carrier to inhibition by the phosphotransferase system due to substitutions of amino acid residues in the carrier of Salmonella typhimurium. Kuroda, M., de Waard, S., Mizushima, K., Tsuda, M., Postma, P., Tsuchiya, T. J. Biol. Chem. (1992) [Pubmed]
  3. Primary structure and characteristics of the melibiose carrier of Klebsiella pneumoniae. Hama, H., Wilson, T.H. J. Biol. Chem. (1992) [Pubmed]
  4. Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Gibbons, R.J., Qureshi, J.V. Infect. Immun. (1979) [Pubmed]
  5. A melibiose transporter and an operon containing its gene in Enterobacter cloacae. Okazaki, N., Jue, X.X., Miyake, H., Kuroda, M., Shimamoto, T., Tsuchiya, T. J. Bacteriol. (1997) [Pubmed]
  6. Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes. Sandrin, M.S., Vaughan, H.A., Dabkowski, P.L., McKenzie, I.F. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  7. Histidine-94 is the only important histidine residue in the melibiose permease of Escherichia coli. Pourcher, T., Sarkar, H.K., Bassilana, M., Kaback, H.R., Leblanc, G. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  8. Functional domains of the yeast regulatory protein GAL4. Johnston, S.A., Zavortink, M.J., Debouck, C., Hopper, J.E. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  9. Isolation of the yeast regulatory gene GAL4 and analysis of its dosage effects on the galactose/melibiose regulon. Johnston, S.A., Hopper, J.E. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  10. Cation-coupling in chimeric melibiose carriers derived from Escherichia coli and Klebsiella pneumoniae. The amino-terminal portion is crucial for Na+ recognition in melibiose transport. Hama, H., Wilson, T.H. J. Biol. Chem. (1993) [Pubmed]
  11. Lithium ion-sugar cotransport via the melibiose transport system in Escherichia coli. Measurement of Li+ transport and specificity. Tsuchiya, T., Oho, M., Shiota-Niiya, S. J. Biol. Chem. (1983) [Pubmed]
  12. Carboxyl-terminal truncations of the melibiose carrier of Escherichia coli. Botfield, M.C., Wilson, T.H. J. Biol. Chem. (1989) [Pubmed]
  13. Cysteine mutagenesis of the amino acid residues of transmembrane helix I in the melibiose carrier of Escherichia coli. Ding, P.Z., Wilson, T.H. Biochemistry (2001) [Pubmed]
  14. Melibiose permease of Escherichia coli: structural organization of cosubstrate binding sites as deduced from tryptophan fluorescence analyses. Mus-Veteau, I., Leblanc, G. Biochemistry (1996) [Pubmed]
  15. Conversion of temperature-sensitive to -resistant gene expression due to mutations in the promoter region of the melibiose operon in Escherichia coli. Tamai, E., Shimamoto, T., Tsuda, M., Mizushima, T., Tsuchiya, T. J. Biol. Chem. (1998) [Pubmed]
  16. Molecular cloning and sequencing of a gene from alkaliphilic Bacillus firmus OF4 that functionally complements an Escherichia coli strain carrying a deletion in the nhaA Na+/H+ antiporter gene. Ivey, D.M., Guffanti, A.A., Bossewitch, J.S., Padan, E., Krulwich, T.A. J. Biol. Chem. (1991) [Pubmed]
  17. Solubilization and reconstitution of the melibiose carrier from a plasmid-carrying strain of Escherichia coli. Tsuchiya, T., Ottina, K., Moriyama, Y., Newman, M.J., Wilson, T.H. J. Biol. Chem. (1982) [Pubmed]
  18. Lectin from embryos and oocytes of Xenopus laevis. Purification and properties. Roberson, M.M., Barondes, S.H. J. Biol. Chem. (1982) [Pubmed]
  19. Isolation and functional reconstitution of soluble melibiose permease from Escherichia coli. Roepe, P.D., Kaback, H.R. Biochemistry (1990) [Pubmed]
  20. Inhibition of anti-Gal IgG binding to porcine endothelial cells by synthetic oligosaccharides. Galili, U., Matta, K.L. Transplantation (1996) [Pubmed]
  21. Melibiose, difructose anhydride III and difructose anhydride IV enhance net calcium absorption in rat small and large intestinal epithelium by increasing the passage of tight junctions in vitro. Mineo, H., Hara, H., Shigematsu, N., Okuhara, Y., Tomita, F. J. Nutr. (2002) [Pubmed]
  22. Isolation and preliminary characterization of the GAL4 gene, a positive regulator of transcription in yeast. Laughon, A., Gesteland, R.F. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  23. Mutagenesis of acidic residues in putative membrane-spanning segments of the melibiose permease of Escherichia coli. I. Effect on Na(+)-dependent transport and binding properties. Pourcher, T., Zani, M.L., Leblanc, G. J. Biol. Chem. (1993) [Pubmed]
  24. The inner interhelix loop 4-5 of the melibiose permease from Escherichia coli takes part in conformational changes after sugar binding. Meyer-Lipp, K., Séry, N., Ganea, C., Basquin, C., Fendler, K., Leblanc, G. J. Biol. Chem. (2006) [Pubmed]
  25. Sugar transport. The crr mutation: its effect on repression of enzyme synthesis. Saier, M.H., Roseman, S. J. Biol. Chem. (1976) [Pubmed]
  26. Lectin purification on affinity columns containing reductively aminated disaccharides. Baues, R.J., Gray, G.R. J. Biol. Chem. (1977) [Pubmed]
  27. Disruption of regulatory gene GAL80 in Saccharomyces cerevisiae: effects on carbon-controlled regulation of the galactose/melibiose pathway genes. Torchia, T.E., Hamilton, R.W., Cano, C.L., Hopper, J.E. Mol. Cell. Biol. (1984) [Pubmed]
  28. Physical and genetic characterization of the melibiose operon and identification of the gene products in Escherichia coli. Hanatani, M., Yazyu, H., Shiota-Niiya, S., Moriyama, Y., Kanazawa, H., Futai, M., Tsuchiya, T. J. Biol. Chem. (1984) [Pubmed]
  29. Genetic and molecular analysis of the GAL3 gene in the expression of the galactose/melibiose regulon of Saccharomyces cerevisiae. Torchia, T.E., Hopper, J.E. Genetics (1986) [Pubmed]
  30. Organisation of the regulatory region of the Escherichia coli melibiose operon. Webster, C., Kempsell, K., Booth, I., Busby, S. Gene (1987) [Pubmed]
  31. Polarity of Tn5 insertion mutations in Escherichia coli. Berg, D.E., Weiss, A., Crossland, L. J. Bacteriol. (1980) [Pubmed]
  32. Evidence that intravenously administered alpha-galactosyl carbohydrates reduce baboon serum cytotoxicity to pig kidney cells (PK15) and transplanted pig hearts. Ye, Y., Neethling, F.A., Niekrasz, M., Koren, E., Richards, S.V., Martin, M., Kosanke, S., Oriol, R., Cooper, D.K. Transplantation (1994) [Pubmed]
  33. Novel food-grade plasmid vector based on melibiose fermentation for the genetic engineering of Lactococcus lactis. Boucher, I., Parrot, M., Gaudreau, H., Champagne, C.P., Vadeboncoeur, C., Moineau, S. Appl. Environ. Microbiol. (2002) [Pubmed]
  34. Three-dimensional structure of the sugar symporter melibiose permease from cryo-electron microscopy. Purhonen, P., Lundbäck, A.K., Lemonnier, R., Leblanc, G., Hebert, H. J. Struct. Biol. (2005) [Pubmed]
  35. Production of recombinant alpha-galactosidases in Thermus thermophilus. Fridjonsson, O., Mattes, R. Appl. Environ. Microbiol. (2001) [Pubmed]
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