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. | ||
Format: PDF | Size: 2.1 MB | Download |
Cite the Following Article
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
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Huang, Z.; Chen, S.; Li, X.; Liu, H. Conjugation Methods in Synthetic Glycoconjugate Vaccines. Chemistry–Methods 2024, 4. doi:10.1002/cmtd.202300054
- Compostella, F.; Morelli, L.; Lay, L. doi:10.1002/9783527831326.ch1
- Rohokale, R.; Guo, Z. Development in the Concept of Bacterial Polysaccharide Repeating Unit-Based Antibacterial Conjugate Vaccines. ACS infectious diseases 2023, 9, 178–212. doi:10.1021/acsinfecdis.2c00559
- Shivatare, S. S.; Shivatare, V. S.; Wong, C.-H. Glycoconjugates: Synthesis, Functional Studies, and Therapeutic Developments. Chemical reviews 2022, 122, 15603–15671. doi:10.1021/acs.chemrev.1c01032
- Donahue, T. C.; Zong, G.; O'Brien, N. A.; Ou, C.; Gildersleeve, J. C.; Wang, L.-X. Synthesis and Immunological Study of N-Glycan-Bacteriophage Qβ Conjugates Reveal Dominant Antibody Responses to the Conserved Chitobiose Core. Bioconjugate chemistry 2022, 33, 1350–1362. doi:10.1021/acs.bioconjchem.2c00211
- Wang, N.; Kong, Y.; Li, J.; Hu, Y.; Li, X.; Jiang, S.; Dong, C. Synthesis and application of phosphorylated saccharides in researching carbohydrate-based drugs. Bioorganic & medicinal chemistry 2022, 68, 116806. doi:10.1016/j.bmc.2022.116806
- Del Bino, L.; Østerlid, K. E.; Wu, D.-Y.; Nonne, F.; Romano, M. R.; Codée, J.; Adamo, R. Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance. Chemical reviews 2022, 122, 15672–15716. doi:10.1021/acs.chemrev.2c00021
- Pietri, G. P.; Tontini, M.; Brogioni, B.; Oldrini, D.; Robakiewicz, S.; Henriques, P.; Calloni, I.; Abramova, V.; Santini, L.; Malić, S.; Miklić, K.; Lisnić, B.; Bertuzzi, S.; Unione, L.; Balducci, E.; de Ruyck, J.; Romano, M.; Jiménez-Barbero, J.; Bouckaert, J.; Jonjić, S.; Rovis, T. L.; Adamo, R. Elucidating the Structural and Minimal Protective Epitope of the Serogroup X Meningococcal Capsular Polysaccharide. Frontiers in molecular biosciences 2021, 8, 745360. doi:10.3389/fmolb.2021.745360
- Morelli, L.; Lay, L.; Santana-Mederos, D.; Valdés-Balbín, Y.; Bencomo, V. V.; van Diepen, A.; Hokke, C. H.; Chiodo, F.; Compostella, F. ACS Chemical Biology - Glycan Array Evaluation of Synthetic Epitopes between the Capsular Polysaccharides from Streptococcus pneumoniae 19F and 19A. ACS chemical biology 2021, 16, 1671–1679. doi:10.1021/acschembio.1c00347
- Sato, K.; Hagio, T.; Sano, M.; Muramoto, K.; Yaoita, A.; Noro, M.; Hara, R. I.; Wada, T. Solid-Phase Stereocontrolled Synthesis of Oligomeric P-Modified Glycosyl Phosphate Derivatives Using the Oxazaphospholidine Method. ACS omega 2021, 6, 20026–20041. doi:10.1021/acsomega.1c03058
- Berti, F.; Romano, M.; Micoli, F.; Adamo, R. Carbohydrate based meningococcal vaccines: past and present overview. Glycoconjugate journal 2021, 38, 401–409. doi:10.1007/s10719-021-09990-y
- Basu, N.; Ghosh, R. Recent chemical syntheses of bacteria related oligosaccharides using modern expeditious approaches. Carbohydrate research 2021, 507, 108295. doi:10.1016/j.carres.2021.108295
- Mettu, R.; Chen, C.-Y.; Wu, C.-Y. Synthetic carbohydrate-based vaccines: challenges and opportunities. Journal of biomedical science 2020, 27, 1–22. doi:10.1186/s12929-019-0591-0
- Zamyatina, A.; Strobl, S. Synthesis of bioactive lipid A and analogs. Recent Trends in Carbohydrate Chemistry; Elsevier, 2020; pp 51–102. doi:10.1016/b978-0-12-820954-7.00003-7
- Dalal, J.; Rana, R.; Harale, K. R.; Hanif, S.; Kumar, N.; Singh, D.; Chhikara, M. K. Development and pre-clinical evaluation of a synthetic oligosaccharide-protein conjugate vaccine against Neisseria meningitidis serogroup C. Vaccine 2019, 37, 5297–5306. doi:10.1016/j.vaccine.2019.07.053
- MacCalman, T.; Phillips-Jones, M. K.; Harding, S. E. Glycoconjugate vaccines: some observations on carrier and production methods. Biotechnology & genetic engineering reviews 2019, 35, 93–125. doi:10.1080/02648725.2019.1703614
- Morelli, L.; Fallarini, S.; Lombardi, G.; Colombo, C.; Lay, L.; Compostella, F. Synthesis and biological evaluation of a trisaccharide repeating unit derivative of Streptococcus pneumoniae 19A capsular polysaccharide. Bioorganic & medicinal chemistry 2018, 26, 5682–5690. doi:10.1016/j.bmc.2018.10.016
- Colombo, C.; Pitirollo, O.; Lay, L. Recent Advances in the Synthesis of Glycoconjugates for Vaccine Development. Molecules (Basel, Switzerland) 2018, 23, 1712. doi:10.3390/molecules23071712
- Hlozek, J.; Kuttel, M. M.; Ravenscroft, N. Conformations of Neisseria meningitidis serogroup A and X polysaccharides: The effects of chain length and O-acetylation. Carbohydrate research 2018, 465, 44–51. doi:10.1016/j.carres.2018.06.007
- Hara, R. I.; Yaoita, A.; Takeda, K.; Ueki, H.; Ishii, A.; Imoto, H.; Kobayashi, S.; Sano, M.; Noro, M.; Sato, K.; Wada, T. Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method. ChemistryOpen 2018, 7, 439–446. doi:10.1002/open.201800030
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.
- GILL DAVINDER; CHHIKARA MANOJ KUMAR; RANA RAKESH; DALAL JUNED; SINGH DEEPTI. AN IMPROVED PROCESS OF CONJUGATION AND NOVEL SYNTHETIC OLIGOSACCHARIDE- PROTEIN CONJUGATES OBTAINED THEREOF. EP 3204396 A4, March 28, 2018.
- 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.