High-Sensitivity and Low-Toxicity Fucose Probe for Glycan Imaging and Biomarker Discovery

Yasuhiko Kizuka, Sho Funayama, Hidehiko Shogomori, Miyako Nakano, Kazuki Nakajima, Ritsuko Oka, Shinobu Kitazume, Yoshiki Yamaguchi, Masahiro Sano, Hiroaki Korekane, Tsui Ling Hsu, Hsiu Yu Lee, Chi Huey Wong, Naoyuki Taniguchi

研究成果: Article査読

24 被引用数 (Scopus)


Fucose, a terminal sugar in glycoconjugates, critically regulates various physiological and pathological phenomena, including cancer development and inflammation. However, there are currently no probes for efficient labeling and detection of this sugar. We chemically synthesized a novel series of alkynyl-fucose analogs as probe candidates and found that 7-alkynyl-fucose gave the highest labeling efficiency and low cytotoxicity. Among the fucose analogs, 7-alkynyl-fucose was the best substrate against all five fucosyltransferases examined. We confirmed its conversion to the corresponding guanosine diphosphate derivative in cells and found that cellular glycoproteins were labeled much more efficiently with 7-alkynyl-fucose than with an existing probe. 7-Alkynyl-fucose was detected in the N-glycan core by mass spectrometry, and 7-alkynyl-fucose-modified proteins mostly disappeared in core-fucose-deficient mouse embryonic fibroblasts, suggesting that this analog mainly labeled core fucose in these cells. These results indicate that 7-alkynyl-fucose is a highly sensitive and powerful tool for basic glycobiology research and clinical application for biomarker discovery.

ジャーナルCell Chemical Biology
出版ステータスPublished - 21-07-2016

All Science Journal Classification (ASJC) codes

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬理学
  • 創薬
  • 臨床生化学


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