Stereocontrolled and convergent entry to CF2-sialosides: Synthesis of CF2-linked ganglioside GM4

Go Hirai; Toru Watanabe; Kazunori Yamaguchi; Taeko Miyagi; Mikiko Sodeoka

doi:10.1021/ja075738w

Stereocontrolled and convergent entry to CF₂-sialosides: Synthesis of CF₂-linked ganglioside GM4

Go Hirai, Toru Watanabe, Kazunori Yamaguchi, Taeko Miyagi, Mikiko Sodeoka

Research output: Contribution to journal › Article › peer-review

63 Citations (Scopus)

Abstract

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) α(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 α(2,3)sialylgalactose and CF₂-linked GM4 were synthesized.

Original language	English
Pages (from-to)	15420-15421
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	50
DOIs	https://doi.org/10.1021/ja075738w
Publication status	Published - Dec 19 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Miyagi, Taeko

AU - Sodeoka, Mikiko

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AB - 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) α(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 α(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

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Stereocontrolled and convergent entry to CF₂-sialosides: Synthesis of CF₂-linked ganglioside GM4

Abstract

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