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

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

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)557-566
ページ数10
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
56
7
DOI
出版ステータスPublished - 1998 1 1
外部発表はい

ASJC Scopus subject areas

  • Organic Chemistry

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