Development of a Stereoselective C-glycosylation and Glycamino Acid-Based New Carbohydrate Analog

Yoshitomo Suhara, Yasuhiro Igarashi, Mie Ichikawa, Masayuki Izumi, Yoshitaka Ichikawa

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Abstract

Glycamino acids are C-glycoside derivatives that possess a C-1 carboxylate and an amino group replacing one of the hydroxyl groups of the monosaccharide moiety. For their preparation, an efficient α-stereoselective C-glycosyl cyanation procedure has been developed by an ethylthio glycoside and TMSCN in the presence of MeOTf. Assembly of oligomers composed of glycamino acid and of hybrid composed of glycamino acid and β-amino acid was carried out in a manner similar to that used for peptide synthesis. Those oligomers were found to be potent inhibitors of HIV infection, sialyl Lewis X -selectin interaction and tumor cell invasion in a sequence specific manner.

Original languageEnglish
Pages (from-to)557-566
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume56
Issue number7
DOIs
Publication statusPublished - 1998 Jan 1

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Keywords

  • Amido-linked
  • Analogs
  • Anti-HIV activity
  • C-glycosides
  • Glycamino acid
  • Oligosaccharide, peptide

ASJC Scopus subject areas

  • Organic Chemistry

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