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 β‐D‐galactoside (Gal C12) as primer. The primer was conveniently prepared in two steps: glycosylation, followed by deacetylation. The primer was in...

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Bibliographic Details
Published in:Chemistry & biodiversity 2010-02, Vol.7 (2), p.440-446
Main Authors: Kasuya, Maria Carmelita Z., Hatanaka, Kenichi
Format: Article
Language:English
Subjects:
Animals
Biosynthesis
Ceramides
Dodecyl β-D-galactoside primer
Gangliosides
Glycolipid analogues
Glycolipids - biosynthesis
Glycolipids - chemical synthesis
Glycolipids - chemistry
Glycosylation
Mice
Mouse melanoma B16 cells
Sialosylgalactosyl ceramide
Stereoselective synthesis
Tumor Cells, Cultured
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Summary:A glycolipid analogue, GM4‐type ganglioside, was obtained by a combination of chemical synthesis and biosynthetic processes in animal cells with dodecyl β‐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.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.200900176