1-N-Iminosugars: Potent and selective inhibitors of β-glycosidases

Yoshitaka Ichikawa, Yasuhiro Igarashi, Mie Ichikawa, Yoshitomo Suhara

研究成果: Article査読

227 被引用数 (Scopus)


A series of 1-N-iminosugars were synthesized to supply the need for glycosidase inhibitors that are both highly potent and selective for β- glycosidases. Designed on the basis of the transition-state model of the β- glucosidase reaction, these iminosugar inhibitors differ from the currently available inhibitors in possessing a nitrogen atom at the anomeric position of the pyranose ring, thereby generating a positive charge on the anomeric position rather than on the ring oxygen of the sugar. Their syntheses, starting with a readily available carbohydrate derivative, involve (i) introduction of an amino functionality as an azido group, (ii) formation of a 1-N-iminopyranose ring with reductive amination, and (iii) stereoselective introduction of a hydroxymethyl or methyl group and were accomplished in a highly stereoselective and efficient manner. The inhibitory potencies of the 1-N-iminosugars were evaluated against several α- and β-glycosidases, and they were found to be extremely potent and highly specific against the corresponding β-glycosidases, with K(i) values in the nanomolar range.

ジャーナルJournal of the American Chemical Society
出版ステータスPublished - 1998 4月 8

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学


「1-N-Iminosugars: Potent and selective inhibitors of β-glycosidases」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。