Globotriaosyl ceramide

K. Matsuoka, M. Terabatake, Y. Esumi, D. Terunuma, and H. Kuzuhara, Synthetic assembly of trisaccharide moieties of globotriaosyl ceramide using carbosilane dendrimers as cores. A new type of functional glyco-material, Tetrahedron Lett., 40 (1999) 7839-7842. 

Figure 1 Structure of the glycosphingolipid, globotriaosyl ceramide. Gal 1 -4 Cain 1 -4 glucosyl ceramide. The three lowest energy conformations as calculated by molecular modeling (3) are shown.

Lactosyl ceramide synthase is a pi-4 galactosyl transferase (40). Lactosyl ceramide is the only glycoconjugate that contains lactose (as opposed to lactosamine). Lactosyl ceramide is the substrate for several glycosyl transferases that then define a core sequence of glycosphingolipids. The Globo series is defined by an al-4 galactosyl transferase activity (41, 42) to make initially globotriaosyl ceramide [also defined as the p ... 

YU, Okita H, Okuda K, Fujimoto J. Shiga toxin binding to globotriaosyl ceramide induces intracellular signals that mediate 134. 

Mylvaganam M, Lingwood C. Adamantyl globotriaosyl ceramide—a monovalent soluble glycolipid mimic which inhibits verotoxin binding to its glycolipid receptor. Biochem. Biophys. 209. Res. Commun. 1999 257 391-394. 

A related strategy was used for synthesis of a more complex carbohydrate, the trisaccharide moiety of globotriaosyl ceramide (Gb3) [10b] (Scheme 3.19). In this reaction an acyl-based fluorous protecting group was used to facilitate the intermediate purification steps in a similar way as can be achieved by solid phase carbohydrate chemistry [12]. 

Khine A.A., Lingwood C.A., Functional significance of globotriaosyl ceramide in interferon-alpha(2)/type 1 interferon receptor-mediated antiviral activity, Journal of Cellular Physiology 182 (2000) 97-108. 

Maloney M.D., Lingwood C.A., CD19 has a potential CD77 (globotriaosyl ceramide)-binding site with sequence similarity to verotoxin B-subunits implications of molecular mimicry for B cell adhesion and enterohemorrhagic Escherichia coh pathogenesis. Journal of Experimental Medicine 180 (1994) 191-201. 

This strategy was successfully applied fo a practical synthesis of a trisaccharide part of globotriaosyl ceramide. A highly fluorinated carboxyUc acid (Hfb) was also prepared and used for rapid and large-scale synthesis of a thyrotropin-releasing hormone (TRH). ... 

Lund N, Branch DR, Mylvaganam M, et al. A novel soluble mimic of the glycolipid, globotriaosyl ceramide inhibits HIV infection. AIDS. 2006 20(3) 333-343. 

Kiarash A, Boyd B, Lingwood CA Glycosphingolipid receptor function is modified by fatty acid content Verotoxin 1 and verotoxin 2c preferentially recognize different globotriaosyl ceramide fatty acid homologues. J. Biol. Chem. 1994 269 11138-11146. 

Arab, S. and Lingwood, C. A., Influence of phospholipid chain length on verotoxin/ globotriaosyl ceramide binding in model membranes comparison of a surface bilayer film and... 

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