Issue 21, 2009

Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae19F capsular polysaccharide

Abstract

The synthesis of a carba-analogue corresponding to the trisaccharide repeating unit of Streptococcus pneumoniae type 19F capsular polysaccharide, where a residue of carba-L-rhamnose has been inserted into the natural trisaccharide in place of L-rhamnose, is described. The conformational properties of the analogue were investigated with the aid of molecular dynamics simulations and were strictly analogous to those of the natural compound. The biological activity of the carba-analogue was comparable to that of the corresponding natural repeating unit, thus suggesting that this compound, more stable to hydrolysis, is a good mimic of the natural structure.

Graphical abstract: Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae19F capsular polysaccharide

Supplementary files

Article information

Article type
Paper
Submitted
10 Jun 2009
Accepted
20 Jul 2009
First published
20 Aug 2009

Org. Biomol. Chem., 2009,7, 4428-4436

Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae19F capsular polysaccharide

L. Legnani, S. Ronchi, S. Fallarini, G. Lombardi, F. Campo, L. Panza, L. Lay, L. Poletti, L. Toma, F. Ronchetti and F. Compostella, Org. Biomol. Chem., 2009, 7, 4428 DOI: 10.1039/B911323A

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