Glycosylation of lactosylceramide analogs in animal cells: amphipathic disaccharide primers for glycosphingolipid synthesis

Biochemical and Biophysical Research Communications
Y Miura, T Yamagata

Abstract

N-Acylaminoethyl lactosides as lactosylceramide analogs as well as n-alkyl lactosides were examined for their ability to prime glycosphingolipid (GSL) synthesis in mouse melanoma B16 cells. Using compounds radiolabeled in a galactose residue and having nondegradable thioglucosidic linkages in lactoside, direct glycosylation was shown to occur at the terminal galactose residue of lactosides subsequent to uptake by cells and dissemination into Golgi compartments. B16 cells took in lactosides temperature-dependently to the point of saturation. All lactosides were taken up and glycosylated by B16 cells. C8-lactosides could not settle on the plasma membrane, while C16-lactosides remained within the cells. Glycosylation in all cases was cellular GSL-specific, suggesting the involvement of glycosyltransferases in GSL synthesis during glycosylation of lactosides. The priming of GSL synthesis by lactosides inhibited the cell surface expression of endogenous GM3 in B16 cells. Lactosylceramide analogs are thus shown useful as primers for glycosylation and to modify GSL expression, and these features should facilitate clarification of the functions of GSLs which have yet to be elucidated.

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Citations

Nov 6, 2007·Chemistry Central Journal·Atsushi MiyagawaKenichi Hatanaka
Jun 24, 2010·Analytical Biochemistry·Tomohisa KatoKenichi Hatanaka
Mar 23, 2004·Biochemical and Biophysical Research Communications·Maria Carmelita Z KasuyaKenichi Hatanaka
Feb 14, 2015·Chemistry & Biodiversity·Tamami KimuraKoji Matsuoka
Dec 29, 2006·Chemistry & Biodiversity·Yoshimi MurozukaKenichi Hatanaka
Aug 26, 1998·The Journal of Biological Chemistry·W H TaylorJ D Esko
Apr 10, 1999·The Journal of Biological Chemistry·R MiuraY Yamaguchi
Oct 12, 2012·Molecular and Cellular Biochemistry·Yinan WangToshinori Sato

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