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Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP-4 Isolated from Feather Star Comanthus japonica
- Goto, Kenta, Tamai, Hideki, Takeda, Yoh, Tanaka, Hide-Nori, Mizuno, Takashi, Imamura, Akihiro, Ishida, Hideharu, Kiso, Makoto, Ando, Hiromune
- Organic letters 2019 v.21 no.11 pp. 4054-4057
- ceramides, chemical reactions, chemical structure, inositols, nerve growth factor, regioselectivity, sialic acid
- 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.