Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2

Chemistry, an Asian Journal
Shinya NakashimaMakoto Kiso

Abstract

The first total synthesis of the hybrid ganglioside X2, which consisted of a highly branched octasaccharide and ceramide moieties, was accomplished by using a glucosyl ceramide cassette approach. With a disaccharyl donor, the heptasaccharide could not be constructed by glycosylation of the C4 hydroxy group of galactose at the reducing end of the pentasaccharide. In contrast, through an alternative approach with two branched glycan units, a GM2-core trisaccharide, and a lacto-ganglio tetrasaccharide, the heptasaccharyl donor could be prepared and subsequently joined with a glucosyl ceramide cassette to afford the protected ganglioside, X2. Finally, global deprotection completed the synthesis, thus affording the pure ganglioside X2.

References

Aug 10, 2006·Glycoconjugate Journal·Tomoaki FuseYu-Teh Li
Feb 16, 2008·Glycoconjugate Journal·Takeru YoshikawaMakoto Kiso
Oct 8, 2011·Bioscience, Biotechnology, and Biochemistry·Hiroyo ShimizuMakoto Kiso

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Citations

May 21, 2014·Journal of Neuroimmunology·Nobuhiro YukiKoichi Hirata
Dec 18, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Miku KonishiMakoto Kiso
Apr 5, 2016·Nature Chemical Biology·Naoko KomuraMakoto Kiso
May 14, 2016·Chemistry : a European Journal·Kenta GotoMakoto Kiso
Sep 25, 2015·Organic & Biomolecular Chemistry·Haruka HiroseMakoto Kiso
Aug 14, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tomohiro NoharaMakoto Kiso
Jun 23, 2020·Chemistry : a European Journal·Kazuki InabaKazunobu Toshima
Aug 22, 2017·European Journal of Organic Chemistry·Yunpeng LiuJunqiang Fang
Jul 25, 2017·Biochimica Et Biophysica Acta. General Subjects·Kenichi G N SuzukiAkihiro Kusumi
May 25, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Amol M VibhuteHiromune Ando
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo

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