Supporting Information
Supporting Information File 1: Experimental procedures for compounds 2–13, 16, 17, 18a, 18b, 19, 20, protocols of biological evaluation and copies of NMR spectra of compounds 8, 9, 10, 16, 17. | ||
Format: PDF | Size: 1.4 MB | Download |
Cite the Following Article
Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope
Manuel Johannes, Maximilian Reindl, Bastian Gerlitzki, Edgar Schmitt and Anja Hoffmann-Röder
Beilstein J. Org. Chem. 2015, 11, 155–161.
https://doi.org/10.3762/bjoc.11.15
How to Cite
Johannes, M.; Reindl, M.; Gerlitzki, B.; Schmitt, E.; Hoffmann-Röder, A. Beilstein J. Org. Chem. 2015, 11, 155–161. doi:10.3762/bjoc.11.15
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
- Wei, X.; Wang, P.; Liu, F.; Ye, X.; Xiong, D. Drug Discovery Based on Fluorine-Containing Glycomimetics. Molecules (Basel, Switzerland) 2023, 28, 6641. doi:10.3390/molecules28186641
- Zhang, H.; Mei, H.; Li, M.; Liu, Z.; Han, J.; Cao, Y. A review: Deoxy-fluorination of galactose – One of lignocellulosic biomass hydrolysates. Industrial Crops and Products 2023, 197, 116671. doi:10.1016/j.indcrop.2023.116671
- Mestre, J.; Bascuas, I.; Bernús, M.; Castillón, S.; Boutureira, O. Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1,2-trans glycosylation. Organic Chemistry Frontiers 2023, 10, 2405–2415. doi:10.1039/d3qo00274h
- Mondal, U. K.; Barchi, J. J. Isolipoic acid-linked gold nanoparticles bearing the thomsen friedenreich tumor-associated carbohydrate antigen: Stability and in vitro studies. Frontiers in chemistry 2022, 10, 1002146. doi:10.3389/fchem.2022.1002146
- Dal Colle, M. C. S.; Fittolani, G.; Delbianco, M. Synthetic Approaches to Break the Chemical Shift Degeneracy of Glycans. Chembiochem : a European journal of chemical biology 2022, 23, e202200416. doi:10.1002/cbic.202200416
- Jensen, D. L.; Trinderup, H. H.; Skovbo, F.; Jensen, H. H. Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis. Organic & biomolecular chemistry 2022, 20, 4915–4925. doi:10.1039/d2ob00939k
- Zhu, M.; Ghouilem, J.; Messaoudi, S. Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines. ACS organic & inorganic Au 2022, 2, 351–358. doi:10.1021/acsorginorgau.2c00006
- Jakubec, M.; Císařová, I.; Karban, J.; Sýkora, J. The Effect of Deoxyfluorination on Intermolecular Interactions in the Crystal Structures of 1,6-Anhydro-2,3-epimino-hexopyranoses. Molecules (Basel, Switzerland) 2022, 27, 278. doi:10.3390/molecules27010278
- Lin, H.; Hong, H.; Feng, L.; Shi, J.; Zhou, Z.; Wu, Z. Synthesis of DNP-modified GM3-based anticancer vaccine and evaluation of its immunological activities for cancer immunotherapy. Chinese Chemical Letters 2021, 32, 4041–4044. doi:10.1016/j.cclet.2021.04.034
- Kurfiřt, M.; Dračínský, M.; Šťastná, L. Č.; Cuřínová, P.; Hamala, V.; Hovorková, M.; Bojarová, P.; Karban, J. Selectively Deoxyfluorinated N-Acetyllactosamine Analogues as 19F NMR Probes to Study Carbohydrate-Galectin Interactions. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 13040–13051. doi:10.1002/chem.202101752
- Hamala, V.; Šťastná, L. Č.; Kurfiřt, M.; Cuřínová, P.; Dračínský, M.; Karban, J. Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides. Beilstein journal of organic chemistry 2021, 17, 1086–1095. doi:10.3762/bjoc.17.85
- Kurfiřt, M.; Lucie, Č. Š.; Cuřínová, P.; Hamala, V.; Karban, J. Development of α-Selective Glycosylation for the Synthesis of Deoxyfluorinated TN Antigen Analogues. The Journal of organic chemistry 2021, 86, 5073–5090. doi:10.1021/acs.joc.0c03015
- Andrea, V. R.-M.; German, J. P.-C.; Karen, J. C.-M.; Javier, E. G.-C. Development of Strategies for Glycopeptide Synthesis: An Overview on the Glycosidic Linkage. Current Organic Chemistry 2020, 24, 2475–2497. doi:10.2174/1385272824999200701121037
- Liu, J.; Schleyer, K. A.; Bryan, T. L.; Xie, C.; Seabra, G. M.; Xu, Y.; Kafle, A.; Cui, C.; Wang, Y.; Yin, K.; Fetrow, B.; Henderson, P. K. P.; Fatland, P. Z.; Liu, J.; Li, C.; Guo, H.; Cui, L. Ultrasensitive small molecule fluorogenic probe for human heparanase. Chemical science 2020, 12, 239–246. doi:10.1039/d0sc04872k
- Bennai, N.; Ibrahim, N.; Marrot, J.; Belkadi, M.; Alami, M.; Magnier, E.; Anselmi, E.; Messaoudi, S. Synthesis of S‐Trifluoromethyl S‐Arylsulfoximine Thioglycosides through Pd‐Catalyzed Migita Cross‐Coupling. European Journal of Organic Chemistry 2020, 2020, 4972–4981. doi:10.1002/ejoc.202000821
- Linclau, B.; Ardá, A.; Reichardt, N.-C.; Sollogoub, M.; Unione, L.; Vincent, S. P.; Jiménez-Barbero, J. Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives. Chemical Society reviews 2020, 49, 3863–3888. doi:10.1039/c9cs00099b
- Kilpin, K. J.; Gusthart, J. S.; Allman, S.; Linclau, B.; Lee, S. S. Enzymatic glycosylation involving fluorinated carbohydrates. Organic & biomolecular chemistry 2020, 18, 3423–3451. doi:10.1039/d0ob00436g
- Bermejo, I. A.; Navo, C. D.; Castro-López, J.; Guerreiro, A.; Jiménez-Moreno, E.; Fernández, E. M. S.; Garcia-Martin, F.; Hinou, H.; Nishimura, S.-I.; Fernández, J. M. G.; Mellet, C. O.; Avenoza, A.; Busto, J. H.; Bernardes, G. J. L.; Hurtado-Guerrero, R.; Peregrina, J. M.; Corzana, F. Synthesis, conformational analysis and in vivo assays of an anti-cancer vaccine that features an unnatural antigen based on an sp2-iminosugar fragment. Chemical science 2020, 11, 3996–4006. doi:10.1039/c9sc06334j
- Franconetti, A.; López, Ó.; Fernández-Bolaños, J. G. Carbohydrates: Potential Sweet Tools Against Cancer. Current medicinal chemistry 2020, 27, 1206–1242. doi:10.2174/0929867325666180719114150
- Zhu, M.; Alami, M.; Messaoudi, S. Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides. Chemical communications (Cambridge, England) 2020, 56, 4464–4467. doi:10.1039/d0cc01126f