Easy production of a glycolipid analogue using animal cells in culture.
A glycolipid analogue, GM4-type ganglioside, was obtained by a combination of chemical synthesis and biosynthetic processes in animal cells with dodecyl beta-D-galactoside (Gal C12) as primer. The primer was conveniently prepared in two steps: glycosylation, followed by deacetylation. The primer was introduced to mouse melanoma B16 cells to serve as substrate for cellular, enzyme-catalyzed glycosylation. Incubation of the cells in the presence of the primer resulted in sialylation of the galactose residue to afford a GM4 analogue that was released from the cells to the culture medium. The strategy of preparation of the GM4 analogue described in this study is a viable alternative to the existing methods. The saccharide-primer method is fast, convenient, not requiring expensive enzymes and glycosyl donors, and highly stereoselective.
Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
Maria Carmelita Z
MC
Kasuya
Kenichi
K
Hatanaka
D000818:Animals; D006017:Glycolipids / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D051379:Mice; D014407:Tumor Cells, Cultured
D006017:Glycolipids