Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa

Isao Ohtsuka, Noriyasu Hada, Misaki Kanemaru, Takanari Fujii, Toshiyuki Atsumi, Nobuko Kakiuchi

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3 Citations (Scopus)

Abstract

The glycosphingolipid neurosporaside (α-D-Glcp-(1→2)-β-D-Galp-(1→6)-β-D-Galp-(1→6)-β-D-Galp-(1→)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (β-D-Galp-(1→6)-β-D-Galp-(1→6)-β-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalCarbohydrate Research
Volume404
DOIs
Publication statusPublished - 2015 Mar 2

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Keywords

  • Glycosphingolipid
  • Neurospora crassa
  • Neurosporaside
  • Oligosaccharide synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Ohtsuka, I., Hada, N., Kanemaru, M., Fujii, T., Atsumi, T., & Kakiuchi, N. (2015). Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa. Carbohydrate Research, 404, 9-16. https://doi.org/10.1016/j.carres.2014.11.018