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

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 Jan 1

Fingerprint

Keywords

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

ASJC Scopus subject areas

Organic Chemistry

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

@article{92a362b2163b4b309793170291630ad5,

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",

month = jan

day = "1",

doi = "10.5059/yukigoseikyokaishi.56.557",

language = "English",

volume = "56",

pages = "557--566",

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

issn = "0037-9980",

publisher = "Society of Synthetic Organic Chemistry",

number = "7",

}

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 - 1998/1/1

Y1 - 1998/1/1

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

U2 - 10.5059/yukigoseikyokaishi.56.557

DO - 10.5059/yukigoseikyokaishi.56.557

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 -

Access to Document

10.5059/yukigoseikyokaishi.56.557