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

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

doi:10.5059/yukigoseikyokaishi.56.557

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

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

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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	https://doi.org/10.5059/yukigoseikyokaishi.56.557
Publication status	Published - 1998
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Organic Chemistry

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10.5059/yukigoseikyokaishi.56.557

Cite this

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title = "Development of a Stereoselective C-glycosylation and Glycamino Acid-Based New Carbohydrate Analog",

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.",

keywords = "Amido-linked, Analogs, Anti-HIV activity, C-glycosides, Glycamino acid, Oligosaccharide, peptide",

author = "Yoshitomo Suhara and Yasuhiro Igarashi and Mie Ichikawa and Masayuki Izumi and Yoshitaka Ichikawa",

year = "1998",

doi = "10.5059/yukigoseikyokaishi.56.557",

language = "English",

volume = "56",

pages = "557--566",

journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",

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publisher = "Society of Synthetic Organic Chemistry",

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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

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JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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