2026-01-20 九州大学
本研究の概要図
<関連情報>
- https://www.kyushu-u.ac.jp/ja/researches/view/1398
- https://www.kyushu-u.ac.jp/f/64470/26_0120_01.pdf
- https://pubs.acs.org/doi/10.1021/jacs.5c17740
β-グルコシルセラミドとβ-グルコシルコレステロールの連鎖編集:β選択的C-グルコシル化と強力なミンクルリガンドの開発 Linkage-Editing of β-Glucosylceramide and β-Glucosylcholesterol: Development of β-Selective C-Glucosylation and Potent Mincle Ligands
Suzuka Chiba,Wakana Kusuhara,Eri Ishikawa,Makoto Yoritate,Taishi Miura,Kazushi Maeda,Haruto Takamura,Hiroaki Matoba,Sho Yamasaki,and Go Hira
Journal of the American Chemical Society Published: January 10, 2026
DOI:https://doi.org/10.1021/jacs.5c17740
Abstract
Despite recent advances, highly stereoselective C-glucosylation for the synthesis of glycan analogs with diverse C-glycoside linkages (linkage-edited pseudoglycans) remains a considerable challenge. Here, we present a β-selective C-glucosylation method using a 2,4-bis(triisopropylsilyl)-protected glucosyl bromide donor. Direct coupling with ceramide and cholesterol-derived bromofluoroolefins provides access to analogs of β-glucosylceramide (pseudo-β-GlcCer) and β-glucosylcholesterol (pseudo-β-GlcChol) containing CH2-, (R)–CHF-, and (S)–CHF-linkages. Pseudo-β-GlcCers activated immune responses in mouse bone marrow-derived macrophages and dendritic cells more potently than native β-GlcCer, with distinct immune activity patterns, depending on the linkage type.
