title: Synthesis of a structural analogue of the repeating unit from Streptococcus pneumoniae 19F capsular polysaccharide based on the cross-metathesis-selenocyclization reaction sequence.
abstract: Pseudo-oligosaccharides have attracted much interest as scaffolds for the synthesis of sugar mimics endowed with very similar biological properties but structurally and synthetically simpler than their natural counterparts. Herein, the synthesis of pseudo-oligosaccharides using the cross-metathesis reaction between distinct sugar-olefins followed by intramolecular selenocyclization of the obtained heterodimer as key steps is first investigated. This methodology has been then applied to the preparation of structural analogues of the trisaccharide repeating unit from Streptococcus pneumoniae 19F. The inhibition abilities of the synthetic molecules were evaluated by a competitive ELISA assay using a rabbit polyclonal anti-19F serum.
authors: Dipartimento di Chimica and ISTM-CNR, Università degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy.
authors: Paolo
authors: P
authors: Ronchi
authors: Catalina
authors: C
authors: Scarponi
authors: Matteo
authors: M
authors: Salvi
authors: Silvia
authors: S
authors: Fallarini
authors: Laura
authors: L
authors: Polito
authors: Enrico
authors: E
authors: Caneva
authors: Luana
authors: L
authors: Bagnoli
authors: Luigi
authors: L
authors: Lay
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013296:Streptococcus pneumoniae / Q000737:chemistry*
chemical_list: D016566:Organoselenium Compounds; D011134:Polysaccharides