Synthesis of fluorescent lactosylceramide stereoisomers

Chemistry and Physics of Lipids
Yidong Liu, Robert Bittman

Abstract

The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-1-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY)-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake.

References

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May 30, 1998·Proceedings of the National Academy of Sciences of the United States of America·C S ChenR E Pagano
Mar 23, 2002·The Journal of Biological Chemistry·Peter MattjusRhoderick E Brown
Aug 20, 2003·Molecular Biology of the Cell·Raman Deep SinghRichard E Pagano

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Citations

Oct 5, 2007·The Journal of Organic Chemistry·Zaiguo Li, Robert Bittman
Jun 24, 2008·Journal of Immunotoxicology·Tomer Adar, Yaron Ilan
Aug 5, 2015·Glycoconjugate Journal·Hongbin YanFengyang Yan
Sep 21, 2013·ELife·Matthias CorrotteNorma W Andrews
Jun 3, 2016·Bioconjugate Chemistry·Martin DaunerValentin Wittmann
Jun 17, 2018·Biological Chemistry·Julian Fink, Jürgen Seibel
Dec 5, 2014·Biological Chemistry·Nigel J Pyne, Richard N Kolesnick
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo

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