C-glycoside analogs

Vyplel, H, Scholz, D, Macher, I, Schindlmaier, K, Schuetze, E, C-glycosidic analogs of lipid A and lipid X synthesis and biological activities, J. Med. Chem., 34, 2159-2161, 1991. 

Synthesis and Evaluation of Anticancer Vaccine Candidates, C-Glycoside Analogs ofSTn and PSA... 

Figure 4. Tumor antigen sTn 0-glycoside 4 and its C-glycoside analog 5.

We then embarked in the synthesis of a double C-glycoside analog of sTn 31 (Schemes 3 and 4) (43). This target was designed to reduce the number of synthetic steps required to prepare 21, to facilitate its conjugation to KLH (Keyhole Limpet Hemocyanin) carrier protein, to further increase biological half-life and to enhance immunological response. 

Human a-l,3-fucosyltransferases are found in milk,51 53 saliva,54 and other specific cell lines.55-57 Through cloning studies, a role for an a-1,3-fucosyltransferase in cell adhesion was identified for the biosynthesis of sialyl Lewisxon neutrophils.58-59 As these studies link a-l,3-fucosyltransferase to cell adhesion and since the activated fucose species used by this enzyme is GDP-L-fucose, Luengo, et al.,eo prepared the C-glycoside analog of GDP-fucose shown in Figure 1.4.4. 

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