Synthesis of a structural analogue of the repeating unit from streptococcus pneumoniae 19F capsular polysaccharide based on the cross-metathesis- selenocyclization reaction sequence (Articolo in rivista)

Type
Label
  • Synthesis of a structural analogue of the repeating unit from streptococcus pneumoniae 19F capsular polysaccharide based on the cross-metathesis- selenocyclization reaction sequence (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo4001146 (literal)
Alternative label
  • Ronchi P.; Scarponi C.; Salvi M.; Fallarini S.; Polito L.; Caneva E.; Bagnoli L.; Lay L. (2013)
    Synthesis of a structural analogue of the repeating unit from streptococcus pneumoniae 19F capsular polysaccharide based on the cross-metathesis- selenocyclization reaction sequence
    in Journal of organic chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Ronchi P.; Scarponi C.; Salvi M.; Fallarini S.; Polito L.; Caneva E.; Bagnoli L.; Lay L. (literal)
Pagina inizio
  • 5172 (literal)
Pagina fine
  • 5183 (literal)
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  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84879310925&partnerID=q2rCbXpz (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 78 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 11 (literal)
Note
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica, ISTM-CNR, Università degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy; Dipartimento di Chimica e Tecnologia Del Farmaco, Sezione di Chimica Organica, Università di Perugia, via del Liceo 1, I-06123 Perugia, Italy; DISCAFF, Università del Piemonte Orientale Amedeo Avogadro, Via Bovio 6, I-28100 Novara, Italy; CNR-ISTM, via Fantoli 16/15, I-20138 Milano, Italy; Centro Interdipartimentale Grandi Apparecchiature (CIGA), via Golgi 19, I-20133 Milano, Italy (literal)
Titolo
  • Synthesis of a structural analogue of the repeating unit from streptococcus pneumoniae 19F capsular polysaccharide based on the cross-metathesis- selenocyclization reaction sequence (literal)
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. © 2013 American Chemical Society. (literal)
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