Blockwise approach to fragments of the O-specific polysaccharide of Shigella flexneri serotype 2a: convergent Synthesis of a decasaccharide representative of a dimer of the branched repeating unit.
J Org Chem
; 69(4): 1060-74, 2004 Feb 20.
Article
em En
| MEDLINE
| ID: mdl-14961653
ABSTRACT
The D'A'B'(E')C'DAB(E)C decasaccharide representative of a dimer of a frame-shifted pentasaccharide repeating unit of the O-specific polysaccharide of Shigella flexneri 2a was synthesized as its methyl glycoside by condensing a pentasaccharide donor (D'A'B'(E')C') and a pentasaccharide acceptor (DAB(E)C-OMe). Several convergent routes to these two building blocks, involving either the AB linkage or the BC linkage as the disconnection site, were evaluated in comparison to the linear strategy. The latter was preferred. It is based on the use of the trichloroacetimidate chemistry. The target branched oligosaccharide was designed to probe the recognition at the molecular level of the natural polysaccharide by protective monoclonal antibodies.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oligossacarídeos
/
Shigella flexneri
/
Antígenos O
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2004
Tipo de documento:
Article
País de afiliação:
França