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 language | English |
|---|---|
| Pages (from-to) | 557-566 |
| Number of pages | 10 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 56 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 1998 Jan 1 |
Keywords
- Amido-linked
- Analogs
- Anti-HIV activity
- C-glycosides
- Glycamino acid
- Oligosaccharide, peptide
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Suhara, Y., Igarashi, Y., Ichikawa, M., Izumi, M., & Ichikawa, Y. (1998). Development of a Stereoselective C-glycosylation and Glycamino Acid-Based New Carbohydrate Analog. Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 56(7), 557-566. https://doi.org/10.5059/yukigoseikyokaishi.56.557