Stereocontrolled and convergent entry to CF2-sialosides:: Synthesis of CF2-linked ganglioside GM4
Stereocontrolled and convergent entry to CF2-sialosides:: Synthesis of CF2-linked ganglioside GM4
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DOI：
10.1021/ja075738w
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发表时间：
2007-12-19
影响因子：
15
通讯作者：
Sodeoka, Mikiko
中科院分区：
文献类型：
--
作者：
Hirai, Go;Watanabe, Toru;Sodeoka, Mikiko
抗唾液酸酶的神经节苷脂类似物具有与天然神经节苷脂相似的生物活性，有望成为阐明神经节苷脂生物学功能的重要探针。以二氟亚甲基连接(CF2连接)α(2，3)唾液酸半乳糖作为抗唾液酸酶神经节苷脂模拟物的核心结构，我们开发了基于爱尔兰-Claisen重排合成CF2-sialoside的新型、立体控制和高效的方法。合成了CF2连接的α(2，3)唾液酸半乳糖和CF2连接的GM4。
Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.