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.

Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae 19F capsular polysaccharide / L. Legnani, S. Ronchi, S. Fallarini, L. Lombardi, F. Campo, L. Panza, L. Lay, L. Poletti, L. Toma, F. Ronchetti, F. Compostella. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 7:21(2009 Nov 07), pp. 4428-4436.

Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae 19F capsular polysaccharide

S. Ronchi
Secondo
;
L. Lay;L. Poletti;F. Ronchetti
Penultimo
;
F. Compostella
Ultimo
2009

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.
Settore BIO/10 - Biochimica
Settore CHIM/06 - Chimica Organica
7-nov-2009
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/68983
Citazioni
  • ???jsp.display-item.citation.pmc??? 4
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 23
social impact