Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP-4 Isolated from Feather Star Comanthus japonica
Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP-4 Isolated from Feather Star Comanthus japonica
复制标题
羽星伞花唾液酸肌醇磷酸鞘脂 CJP-2、CJP-3 和 CJP-4 的全合成
DOI：
10.1021/acs.orglett.9b01229
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Ando Hiromune
中科院分区：
文献类型：
--
作者：
Goto Kenta;Tamai Hideki;Takeda Yoh;Tanaka Hide-Nori;Mizuno Takashi;Imamura Akihiro;Ishida Hideharu;Kiso Makoto;Ando Hiromune
报道了三种棘皮唾液酰肌醇磷脂的首次全合成，它们在缺乏神经生长因子的情况下表现出不寻常的神经生成活性。合成的亮点包括唾液酸上的9- o甲基化，唾液酸残基之间残基间酰胺键的形成，以及高度立体和区域选择性的肌醇唾液酰化。在单、二、三烯醇肌醇和神经酰胺之间形成了一个关键的磷酸二酯键。
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.