Carbohydr Res. 2017 Mar 14;443-444:29-36. doi: 10.1016/j.carres.2017.03.012. [Epub ahead of print]

Synthesis and conformational analysis of a simplified inositol-model of the Streptococcus pneumoniae 19F capsular polysaccharide repeating unit.

Catelani G1, D'Andrea F1, Guazzelli L2, Griselli A1, Testi N1, Chiacchio MA3, Legnani L3, Toma L4.

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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.

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Carbohydrate mimic; Inositol; Streptococcus pneumoniae; Vaccine

PMID: 28324771 DOI: 10.1016/j.carres.2017.03.012