Synthesis of simple sea cucumber ganglioside analogs

Ryuichi Higuchi, Takeshi Mori, Tetsuji Sugata, Koji Yamada, Tomofumi Miyamoto

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Abstract

Two simple sea cucumber ganglioside analogs 8 (NeuAcα2→6 Glcβ 1→1 docosanol) and 9 (NeuAcβ2→6 Glcβ 1→1 docosanol), containing a long-chain alcohol as a mimic of ceramide, have been synthesized. Coupling of the methyl 2-thioglycoside derivative of N-acetylneuraminic acid S with docosyl glucoside derivative 3 afforded the protected ganglioside analogs 6 and 7, which were deprotected to give the corresponding ganglioside analogs 8 and 9, respectively. The 13C-NMR data obtained for these anomers 8 and 9 should prove useful for the determination of anomeric configurations of sialic acid residues in gangliosides.

Original languageEnglish
Pages (from-to)3175-3178
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number11
Publication statusPublished - Nov 1 1999

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Higuchi, R., Mori, T., Sugata, T., Yamada, K., & Miyamoto, T. (1999). Synthesis of simple sea cucumber ganglioside analogs. European Journal of Organic Chemistry, (11), 3175-3178.