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 |
| Publication status | Published - 1998 |
| Externally published | Yes |
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Keywords
- Amido-linked
- Analogs
- Anti-HIV activity
- C-glycosides
- Glycamino acid
- Oligosaccharide, peptide
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Development of a Stereoselective C-glycosylation and Glycamino Acid-Based New Carbohydrate Analog. / Suhara, Yoshitomo; Igarashi, Yasuhiro; Ichikawa, Mie; Izumi, Masayuki; Ichikawa, Yoshitaka.
In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 56, No. 7, 1998, p. 557-566.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Development of a Stereoselective C-glycosylation and Glycamino Acid-Based New Carbohydrate Analog
AU - Suhara, Yoshitomo
AU - Igarashi, Yasuhiro
AU - Ichikawa, Mie
AU - Izumi, Masayuki
AU - Ichikawa, Yoshitaka
PY - 1998
Y1 - 1998
N2 - 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.
AB - 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.
KW - Amido-linked
KW - Analogs
KW - Anti-HIV activity
KW - C-glycosides
KW - Glycamino acid
KW - Oligosaccharide, peptide
UR - http://www.scopus.com/inward/record.url?scp=0041093851&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0041093851&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0041093851
VL - 56
SP - 557
EP - 566
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 7
ER -