Synthesis of a 'Manno-Gb 3' analogue as a potential shiga toxin/verotoxin inhibitor

K. P. Ravindranathan Kartha; Steven W. Homans; Robert A. Field

Synthesis of a 'Manno-Gb ₃' analogue as a potential shiga toxin/verotoxin inhibitor

K. P. Ravindranathan Kartha, Steven W. Homans, Robert A. Field

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

3 Citations (Scopus)

Abstract

A highly facile stereospecific synthesis of 'manno-Gb3' trisaccharide as its 2-(trimethylsilyl)ethyl glycoside is reported in which the crucial glycosylation reaction of the appropriately protected lactoside acceptor 10 with acetobromomannose was carried out using molecular iodine in excellent yield. The Gb3 analogue 3 is expected to serve as an inhibitor of Shiga/Shiga-like toxins.

Original language	English
Pages (from-to)	14-19
Number of pages	6
Journal	Trends in Carbohydrate Research
Volume	2
Issue number	2
Publication status	Published - 2010

Keywords

'Manno-gb3' synthesis
Iodine-promoted glycosylation
Shiga toxin/verotoxin inhibitor
Stereospecific oligosaccharide synthesis

Cite this

@article{7399c85cd5e24c2f9cb30a2e697b0976,

title = "Synthesis of a 'Manno-Gb 3' analogue as a potential shiga toxin/verotoxin inhibitor",

abstract = "A highly facile stereospecific synthesis of 'manno-Gb3' trisaccharide as its 2-(trimethylsilyl)ethyl glycoside is reported in which the crucial glycosylation reaction of the appropriately protected lactoside acceptor 10 with acetobromomannose was carried out using molecular iodine in excellent yield. The Gb3 analogue 3 is expected to serve as an inhibitor of Shiga/Shiga-like toxins.",

keywords = "'Manno-gb3' synthesis, Iodine-promoted glycosylation, Shiga toxin/verotoxin inhibitor, Stereospecific oligosaccharide synthesis",

author = "Kartha, {K. P. Ravindranathan} and Homans, {Steven W.} and Field, {Robert A.}",

year = "2010",

language = "English",

volume = "2",

pages = "14--19",

journal = "Trends in Carbohydrate Research",

issn = "0975-0304",

publisher = "Association of Carbohydrate Chemists and Technologists",

number = "2",

}

TY - JOUR

T1 - Synthesis of a 'Manno-Gb 3' analogue as a potential shiga toxin/verotoxin inhibitor

AU - Kartha, K. P. Ravindranathan

AU - Homans, Steven W.

AU - Field, Robert A.

PY - 2010

Y1 - 2010

N2 - A highly facile stereospecific synthesis of 'manno-Gb3' trisaccharide as its 2-(trimethylsilyl)ethyl glycoside is reported in which the crucial glycosylation reaction of the appropriately protected lactoside acceptor 10 with acetobromomannose was carried out using molecular iodine in excellent yield. The Gb3 analogue 3 is expected to serve as an inhibitor of Shiga/Shiga-like toxins.

AB - A highly facile stereospecific synthesis of 'manno-Gb3' trisaccharide as its 2-(trimethylsilyl)ethyl glycoside is reported in which the crucial glycosylation reaction of the appropriately protected lactoside acceptor 10 with acetobromomannose was carried out using molecular iodine in excellent yield. The Gb3 analogue 3 is expected to serve as an inhibitor of Shiga/Shiga-like toxins.

KW - 'Manno-gb3' synthesis

KW - Iodine-promoted glycosylation

KW - Shiga toxin/verotoxin inhibitor

KW - Stereospecific oligosaccharide synthesis

UR - http://www.scopus.com/inward/record.url?scp=84861451059&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:84861451059

VL - 2

SP - 14

EP - 19

JO - Trends in Carbohydrate Research

JF - Trends in Carbohydrate Research

SN - 0975-0304

IS - 2

ER -

Synthesis of a 'Manno-Gb 3' analogue as a potential shiga toxin/verotoxin inhibitor

Abstract

Keywords

Other files and links

Cite this

Synthesis of a 'Manno-Gb ₃' analogue as a potential shiga toxin/verotoxin inhibitor