RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

Takuya Tashiro, Ryusuke Nakagawa, Sayo Inoue, Masao Shiozaki, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl β-l-arabinopyranoside. Bioassay showed RCAI-61 to be a much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-γ in vivo.

Original languageEnglish
Pages (from-to)6827-6830
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number48
DOIs
Publication statusPublished - 2008 Nov 24

Keywords

  • CD1d
  • IFN-γ
  • KRN7000
  • α-Galactosylceramides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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