期刊
CARBOHYDRATE RESEARCH
卷 344, 期 12, 页码 1453-1463出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2009.06.009
关键词
a-Series ganglioside; Troc group; GM3 acceptor and GM2 acceptor; Diethylphosphite method; Trichloroacetimidate method
资金
- MEXT of Japan [1701007]
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. (C) 2009 Elsevier Ltd. All rights reserved.
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