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 1, 1992·Muscle & Nerve·N YukiT Miyatake
May 4, 1991·Lancet·N YukiH Sasaki
Dec 1, 1986·Carbohydrate Research·K K SadozaiA Kobata
May 18, 2000·The Journal of Organic Chemistry·M Nitz, D R Bundle
Mar 7, 2006·Carbohydrate Research·Jean-Claude Jacquinet
Aug 10, 2006·Glycoconjugate Journal·Tomoaki FuseYu-Teh Li
Feb 16, 2008·Glycoconjugate Journal·Takeru YoshikawaMakoto Kiso
Jun 24, 2008·Carbohydrate Research·Kohki FujikawaMakoto Kiso
Mar 20, 2009·The Journal of Organic Chemistry·Akihiro ImamuraMakoto Kiso
Jan 6, 2011·Chemistry : a European Journal·Shinya NakashimaMakoto Kiso
Apr 7, 2011·Chemistry : a European Journal·Kohki FujikawaMakoto Kiso
Oct 8, 2011·Bioscience, Biotechnology, and Biochemistry·Hiroyo ShimizuMakoto Kiso
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 4, 2019·Organic & Biomolecular Chemistry·Han ZhangJian Gao
Jul 12, 2017·Chemical Communications : Chem Comm·Abhishek SantraXi Chen
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
Dec 5, 2018·Organic Letters·Barry M TrostWen-Ju Bai
Jan 5, 2021·The Journal of Organic Chemistry·Rajendra S RohokaleZhongwu Guo