Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N

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• 作者：Tatsuya Komori ; Akihiro Imamura ; Hiromune Ando ; Hideharu Ishida ; Makoto Kiso
• 关键词：a-Series ganglioside ; Troc group ; GM3 acceptor and GM2 acceptor ; Diethylphosphite method ; Trichloroacetimidate method
• 刊名：Carbohydrate Research
• 出版年：2009
• 出版时间：17 August 2009
• 年：2009
• 卷：344
• 期：12
• 页码：1453-1463
• 全文大小：852 K

文摘

A first systematic synthesis of the glycan parts of the a-series gangliosides (GT1a, GD1a, and GM1) utilizing the newly developed N-Troc-protected GM3 and galactosaminyl building blocks is described. The key processes, including the assembly of the GM2 sequence and its conversion into the 3-hydroxy acceptor, were facilitated mainly by the high degree of participation and chemoselective cleavability of the Troc group in the galactosaminyl unit. Furthermore, the novel GM2 acceptor served as a good coupling partner during glycosylation with galactosyl, sialyl galactosyl, and disialyl galactosyl donors, successfully producing the GM1, GD1a, and GT1a glycans.