RCAI-56, a carbocyclic analogue of KRN7000: its synthesis and potent activity for natural killer (NK) T cells to preferentially produce interferon-γ

Takuya Tashiro, Ryusuke Nakagawa, Takatsugu Hirokawa, Sayo Inoue, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

RCAI-56 (3), a carbocyclic analogue of KRN7000 (1) was synthesized through an efficient coupling of a carba-α-d-galactose derivative 11 with cyclic sulfamidate derivative 13 of phytosphingosine to give 15. Carbasugar derivative 11 was prepared by starting from methyl α-d-galactopyranoside (4), employing Pd(II)-catalyzed Ferrier rearrangement as the key step. RCAI-56 (3) is a potent stimulant of NKT cells in vivo to induce the production of Th1 biased cytokines such as interferon-γ in mice. According to the docking model of CD1d-3 complex, its stabilization energy is approximately at the same level as that of the CD1d-1 complex.

Original languageEnglish
Pages (from-to)3343-3347
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number19
DOIs
Publication statusPublished - 2007 May 7
Externally publishedYes

Fingerprint

phytosphingosine
Carbasugars
Natural Killer T-Cells
T-cells
Galactose
Interferons
Cytokines
Derivatives
Stabilization
KRN 7000
methyl-galactopyranoside

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

RCAI-56, a carbocyclic analogue of KRN7000 : its synthesis and potent activity for natural killer (NK) T cells to preferentially produce interferon-γ. / Tashiro, Takuya; Nakagawa, Ryusuke; Hirokawa, Takatsugu; Inoue, Sayo; Watarai, Hiroshi; Taniguchi, Masaru; Mori, Kenji.

In: Tetrahedron Letters, Vol. 48, No. 19, 07.05.2007, p. 3343-3347.

Research output: Contribution to journalArticle

Tashiro, Takuya ; Nakagawa, Ryusuke ; Hirokawa, Takatsugu ; Inoue, Sayo ; Watarai, Hiroshi ; Taniguchi, Masaru ; Mori, Kenji. / RCAI-56, a carbocyclic analogue of KRN7000 : its synthesis and potent activity for natural killer (NK) T cells to preferentially produce interferon-γ. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 19. pp. 3343-3347.
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