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Easy Production of a Glycolipid Analogue Using Animal Cells in Culture
Author(s) -
Kasuya Maria Carmelita Z.,
Hatanaka Kenichi
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200900176
Subject(s) - glycosylation , glycolipid , chemistry , primer (cosmetics) , ganglioside , biochemistry , enzyme , chemical synthesis , galactose , glycosyl , stereochemistry , in vitro , organic chemistry
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.