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 journalArticle

47 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 languageEnglish
Pages (from-to)15420-15421
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number50
DOIs
Publication statusPublished - Dec 19 2007
Externally publishedYes

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Gangliosides
Bioactivity
Neuraminidase
Ireland
GM4 ganglioside

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Stereocontrolled and convergent entry to CF2-sialosides : Synthesis of CF2-linked ganglioside GM4. / Hirai, Go; Watanabe, Toru; Yamaguchi, Kazunori; Miyagi, Taeko; Sodeoka, Mikiko.

In: Journal of the American Chemical Society, Vol. 129, No. 50, 19.12.2007, p. 15420-15421.

Research output: Contribution to journalArticle

Hirai, Go ; Watanabe, Toru ; Yamaguchi, Kazunori ; Miyagi, Taeko ; Sodeoka, Mikiko. / Stereocontrolled and convergent entry to CF2-sialosides : Synthesis of CF2-linked ganglioside GM4. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 50. pp. 15420-15421.
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