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Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP‑4 Isolated from Feather Star Comanthus japonica

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journal contribution
posted on 21.05.2019, 14:33 by Kenta Goto, Hideki Tamai, Yoh Takeda, Hide-Nori Tanaka, Takashi Mizuno, Akihiro Imamura, Hideharu Ishida, Makoto Kiso, Hiromune Ando
The first total synthesis of three echinodermatous sialyl inositol phosphosphingolipids, which exhibit unusual neuritogenic activity in the absence of nerve growth factor, are reported. Highlights of the syntheses include 9-O-methylation on sialic acid, inter-residual amide bond formation between sialic acid residues, and highly stereo- and regioselective sialylation of inositol. A key phosphodiester linkage between the mono-, di-, and trisialyl inositols and ceramide was formed at a late state employing the phosphoramidite method.