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Chemical Compound Review

Globotriaose     (2R,3S,4R,5R)-4,5,6- trihydroxy-2,3...

Synonyms: AC1L4XUD, AR-1L8553, P(k) Trisaccharide, Galp-1-4-galp-glcp, Gal-1-4-gal-1-4-glc
 
 
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Disease relevance of Globotriose

 

High impact information on Globotriose

 

Biological context of Globotriose

  • This tetrasaccharide displays the globoside trisaccharide (globotriose) as a terminal epitope, a structure that is found on many human cells (P(k) blood group antigen) and which is thought to be an important virulence determinant for H. influenzae [2].
  • Large scale in vivo synthesis of globotriose and globotetraose by high cell density culture of metabolically engineered Escherichia coli [4].
  • By using standard glycosyltransferase assay and HPLC, we show that LgtD is an N-acetylgalactosaminyltransferase with high donor substrate specificity and globotriose is a highly preferred acceptor substrate for the enzyme [7].
  • Seven aglycon analogs of globotriosylceramide were synthesized by glycosylation of suitable functionalized alcohols with peracetylated globotriose trichloroacetimidate, followed by further transformations of the aglycon and removal of the protecting groups [8].
  • This plasmid was inserted into the E. coli NM522 strain to form globotriose-producing cells ('superbug' pLDR20-CKTUF) [9].
 

Anatomical context of Globotriose

  • More complex ceramide-hexosides, globotriose, globotetraose and blood-group substance H, present in trace amounts in normal brain, were much more abundant in cerebral cortex and especially in white matter of brains affected by Krabbe's disease [10].
 

Gene context of Globotriose

 

Analytical, diagnostic and therapeutic context of Globotriose

  • Recently, three globotriose (Galalpha[1-4] Galbeta [1-4] Glcbeta) binding sites per B-subunit monomer were identified by crystallography [12].
  • The wild-type and mutant Stx1s with amino acid replacements at positions 167 and 170 of the A subunit were purified by one-step affinity chromatography with commercially available Globotriose Fractogel, and the mutant Stxs were used for the immunization of mice [13].
  • Globotriose (5 mg/ml) completely inhibited and reversed cell agglutination and caused a 10- to 100-fold reduction in JR1 binding to target cells, as determined by flow cytometry [6].

References

  1. A mutational analysis of the globotriaosylceramide-binding sites of verotoxin VT1. Soltyk, A.M., MacKenzie, C.R., Wolski, V.M., Hirama, T., Kitov, P.I., Bundle, D.R., Brunton, J.L. J. Biol. Chem. (2002) [Pubmed]
  2. Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b strain RM7004. Masoud, H., Martin, A., Thibault, P., Moxon, E.R., Richards, J.C. Biochemistry (2003) [Pubmed]
  3. Neutralization of Shiga toxins Stx1, Stx2c, and Stx2e by recombinant bacteria expressing mimics of globotriose and globotetraose. Paton, A.W., Morona, R., Paton, J.C. Infect. Immun. (2001) [Pubmed]
  4. Large scale in vivo synthesis of globotriose and globotetraose by high cell density culture of metabolically engineered Escherichia coli. Antoine, T., Bosso, C., Heyraud, A., Samain, E. Biochimie (2005) [Pubmed]
  5. Determination of the cell adhesion specificity of Streptococcus suis with the complete set of monodeoxy analogues of globotriose. Haataja, S., Zhang, Z., Tikkanen, K., Magnusson, G., Finne, J. Glycoconj. J. (1999) [Pubmed]
  6. In vitro and in vivo effects of soluble, monovalent globotriose on bacterial attachment and colonization. Leach, J.L., Garber, S.A., Marcon, A.A., Prieto, P.A. Antimicrob. Agents Chemother. (2005) [Pubmed]
  7. Overexpression and biochemical characterization of beta-1,3-N-acetylgalactosaminyltransferase LgtD from Haemophilus influenzae strain Rd. Shao, J., Zhang, J., Kowal, P., Lu, Y., Wang, P.G. Biochem. Biophys. Res. Commun. (2002) [Pubmed]
  8. Synthesis of some aglycon analogs of globotriosylceramide. Hansen, H.C., Magnusson, G. Carbohydr. Res. (1999) [Pubmed]
  9. Large-scale synthesis of globotriose derivatives through recombinant E. coli. Zhang, J., Kowal, P., Chen, X., Wang, P.G. Org. Biomol. Chem. (2003) [Pubmed]
  10. Chemical pathology of Krabbe's disease. III. Ceramide-hexosides and gangliosides of brain. Vanier, M.T., Svennerholm, L. Acta paediatrica Scandinavica. (1975) [Pubmed]
  11. Synthesis of complex carbohydrates and glyconjugates: enzymatic synthesis of globotetraose using alpha-1,3-N-acetylgalactosaminyltransferase LgtD from Haemophilus infuenzae strain Rd. Ryu, K., Lin, S., Shao, J., Song, J., Chen, M., Wang, W., Li, H., Yi, W., Wang, P.G. Methods Mol. Biol. (2005) [Pubmed]
  12. The identification of three biologically relevant globotriaosyl ceramide receptor binding sites on the Verotoxin 1 B subunit. Bast, D.J., Banerjee, L., Clark, C., Read, R.J., Brunton, J.L. Mol. Microbiol. (1999) [Pubmed]
  13. Protection against Shiga toxin 1 challenge by immunization of mice with purified mutant Shiga toxin 1. Ishikawa, S., Kawahara, K., Kagami, Y., Isshiki, Y., Kaneko, A., Matsui, H., Okada, N., Danbara, H. Infect. Immun. (2003) [Pubmed]
 
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