TY - JOUR
T1 - Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae 19F capsular polysaccharide
AU - Legnani, Laura
AU - Ronchi, Silvia
AU - Fallarini, Silvia
AU - Lombardi, Grazia
AU - Campo, Federica
AU - Panza, Luigi
AU - Lay, Luigi
AU - Poletti, Laura
AU - Toma, Lucio
AU - Ronchetti, Fiamma
AU - Compostella, Federica
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=70350036078&partnerID=8YFLogxK
U2 - 10.1039/b911323a
DO - 10.1039/b911323a
M3 - Article
SN - 1477-0520
VL - 7
SP - 4428
EP - 4436
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 21
ER -