Synthesis and conformational analysis of a simplified inositol-model of the Streptococcus pneumoniae 19F capsular polysaccharide repeating unit.
Carbohydrate mimics have been studied for a long time as useful sugar substitutes, both in the investigation of biological events and in the treatment of sugar-related diseases. Here we report further evaluation of the capabilities of inositols as carbohydrate substitutes. The conformational features of an inositol-model of a simplified repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae 19F has been evaluated by computational analysis, and compared to the native repeating unit. The inositol mimic was synthesized, and its experimental spectroscopic data allowed for verification of the theoretical results.
Università di Pisa, Dipartimento di Farmacia, Via Bonanno 33, 56126 Pisa, Italy.
Giorgio
G
Catelani
Università di Pisa, Dipartimento di Farmacia, Via Bonanno 33, 56126 Pisa, Italy.
Felicia
F
D'Andrea
Università di Pisa, Dipartimento di Farmacia, Via Bonanno 33, 56126 Pisa, Italy. Electronic address: lorenzo.guazzelli@unipi.it.
Lorenzo
L
Guazzelli
Università di Pisa, Dipartimento di Farmacia, Via Bonanno 33, 56126 Pisa, Italy.
Alessio
A
Griselli
Università di Pisa, Dipartimento di Farmacia, Via Bonanno 33, 56126 Pisa, Italy.
Nicola
N
Testi
Università di Catania, Dipartimento di Scienze del Farmaco, V.le A. Doria 6, 95125 Catania, Italy; Università di Pavia, Dipartimento di Chimica, Via Taramelli 12, 27100 Pavia, Italy.
Maria Assunta
MA
Chiacchio
Università di Catania, Dipartimento di Scienze del Farmaco, V.le A. Doria 6, 95125 Catania, Italy; Università di Pavia, Dipartimento di Chimica, Via Taramelli 12, 27100 Pavia, Italy.
Laura
L
Legnani
Università di Pavia, Dipartimento di Chimica, Via Taramelli 12, 27100 Pavia, Italy.
Lucio
L
Toma
D016667:Bacterial Capsules / Q000737:chemistry*; D002236:Carbohydrate Conformation; D060326:Chemistry Techniques, Synthetic; D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D013002:Somatomedins / Q000138:chemical synthesis* / Q000737:chemistry*; D013296:Streptococcus pneumoniae / Q000737:chemistry*
C088268:Biomin H; D013002:Somatomedins; C116177:capsular polysaccharide 19F; D007294:Inositol
Carbohydrate mimic; Inositol; Streptococcus pneumoniae; Vaccine