Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

Laura Morelli, Damiano Cancogni, Marta Tontini, Alberto Nilo, Sara Filippini, Paolo Costantino, Maria Rosaria Romano, Francesco Berti, Roberto Adamo and Luigi Lay
Beilstein J. Org. Chem. 2014, 10, 2367–2376. https://doi.org/10.3762/bjoc.10.247

Supporting Information

Supporting Information File 1: Experimental procedures for the synthesis of compounds 1, 5, 6, 7, 9, 19, copies of 1H NMR and 13C NMR spectra of compounds 5–6 and 1H NMR, 13C NMR and 31P NMR spectra of compounds 1, 7, 9.
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Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments
Laura Morelli, Damiano Cancogni, Marta Tontini, Alberto Nilo, Sara Filippini, Paolo Costantino, Maria Rosaria Romano, Francesco Berti, Roberto Adamo and Luigi Lay
Beilstein J. Org. Chem. 2014, 10, 2367–2376. https://doi.org/10.3762/bjoc.10.247

How to Cite

Morelli, L.; Cancogni, D.; Tontini, M.; Nilo, A.; Filippini, S.; Costantino, P.; Romano, M. R.; Berti, F.; Adamo, R.; Lay, L. Beilstein J. Org. Chem. 2014, 10, 2367–2376. doi:10.3762/bjoc.10.247

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Patents

  • GILL DAVINDER; HARALE KISHORE; CHHIKARA MANOJ KUMAR. Novel synthetic oligomers of Neisseria meningitis serogroup X and process of preparing them. AU 2015221820 B2, Jan 31, 2019.
  • GILL DAVINDER; HARALE KISHORE; CHHIKARA MANOJ KUMAR. Synthetic oligomers of Neisseria meningitis serogroup X and process of preparing them. US 10183962 B2, Jan 22, 2019.
  • ジル,ダビンダー; ハラレ,キショア; チッカラ,マノジュ クマール. 髄膜炎菌(Neisseria meningitidis)血清型Xの新規の合成オリゴマー及びその調製方法. JP 2017512203 A, May 18, 2017.
  • GILL DAVINDER; HARALE KISHORE; CHHIKARA MANOJ KUMAR. Novel synthetic oligomers of neisseria meningitis serogroup x and process of preparing them. CN 106061986 A, Oct 26, 2016.
  • GILL DAVINDER; HARALE KISHORE; CHHIKARA MANOJ KUMAR. NOVEL SYNTHETIC OLIGOMERS OF NEISSERIA MENINGITIS SEROGROUP X AND PROCESS OF PREPARING THEM. WO 2015128797 A1, Sept 3, 2015.
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