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
Externally publishedYes

Fingerprint

Lymphocytes
Bioactivity
Interferons
Galactose
Bioassay
Biological Assay
KRN 7000

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

RCAI-61, the 6′-O-methylated analog of KRN7000 : its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo. / Tashiro, Takuya; Nakagawa, Ryusuke; Inoue, Sayo; Shiozaki, Masao; Watarai, Hiroshi; Taniguchi, Masaru; Mori, Kenji.

In: Tetrahedron Letters, Vol. 49, No. 48, 24.11.2008, p. 6827-6830.

Research output: Contribution to journalArticle

Tashiro, Takuya ; Nakagawa, Ryusuke ; Inoue, Sayo ; Shiozaki, Masao ; Watarai, Hiroshi ; Taniguchi, Masaru ; Mori, Kenji. / RCAI-61, the 6′-O-methylated analog of KRN7000 : its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 48. pp. 6827-6830.
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