Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

Baptiste Thomas, Michele Fiore, Isabelle Bossu, Pascal Dumy and Olivier Renaudet
Beilstein J. Org. Chem. 2012, 8, 421–427. https://doi.org/10.3762/bjoc.8.47

Supporting Information

The Supporting Information file contains analytical details of all heteroglycoclusters of series 2:2 (6-Man/Fuc, 6-Man/Lac, 6-Fuc/Man, 6-Fuc/Lac, 6-Lac/Man and 6-Lac/Fuc) and 3:1 (8-Man/Fuc, 8-Man/Lac, 8-Fuc/Man, 8-Fuc/Lac, 8-Lac/Man and 8-Lac/Fuc) described in this article.

Supporting Information File 1: Crude RP-HPLC profiles and ESI-MS spectra for the heteroglycoclusters.
Format: PDF Size: 2.1 MB Download

Cite the Following Article

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations
Baptiste Thomas, Michele Fiore, Isabelle Bossu, Pascal Dumy and Olivier Renaudet
Beilstein J. Org. Chem. 2012, 8, 421–427. https://doi.org/10.3762/bjoc.8.47

How to Cite

Thomas, B.; Fiore, M.; Bossu, I.; Dumy, P.; Renaudet, O. Beilstein J. Org. Chem. 2012, 8, 421–427. doi:10.3762/bjoc.8.47

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

  • Behren, S.; Westerlind, U. Novel Approaches To Design Glycan‐Based Antibacterial Inhibitors. European Journal of Organic Chemistry 2022, 26. doi:10.1002/ejoc.202200795
  • Goyard, D.; Ortiz, A. M.-S.; Boturyn, D.; Renaudet, O. Multivalent glycocyclopeptides: conjugation methods and biological applications. Chemical Society reviews 2022, 51, 8756–8783. doi:10.1039/d2cs00640e
  • Fray, M.; Mathiron, D.; Pilard, S.; Lesur, D.; Abidi, R.; Barhoumi‐Slimi, T.; Cragg, P. J.; Benazza, M. Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N‐Alkylation of N‐Acylhydrazone. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202101537
  • Niedzwiecka, A.; Achebe, N.; Ling, C.-C. Comprehensive Glycoscience - Glycoclusters and Glycodendrimers. Comprehensive Glycoscience; Elsevier, 2021; pp 263–345. doi:10.1016/b978-0-12-819475-1.00039-0
  • Goyard, D.; Thomas, B.; Gillon, E.; Imberty, A.; Renaudet, O. Heteroglycoclusters With Dual Nanomolar Affinities for the Lectins LecA and LecB From Pseudomonas aeruginosa. Frontiers in chemistry 2019, 7, 666. doi:10.3389/fchem.2019.00666
  • Gade, M.; Alex, C.; Ben-Arye, S. L.; Monteiro, J. T.; Yehuda, S.; Lepenies, B.; Padler-Karavani, V.; Kikkeri, R. Microarray Analysis of Oligosaccharide-Mediated Multivalent Carbohydrate-Protein Interactions and Their Heterogeneity. Chembiochem : a European journal of chemical biology 2018, 19, 1170–1177. doi:10.1002/cbic.201800037
  • Freichel, T.; Eierhoff, S.; Snyder, N. L.; Hartmann, L. Toward Orthogonal Preparation of Sequence-Defined Monodisperse Heteromultivalent Glycomacromolecules on Solid Support Using Staudinger Ligation and Copper-Catalyzed Click Reactions. The Journal of organic chemistry 2017, 82, 9400–9409. doi:10.1021/acs.joc.7b01398
  • Bagul, R. S.; Hosseini, M. M.; Shiao, T. C.; Roy, R. “Onion peel” glycodendrimer syntheses using mixed triazine and cyclotriphosphazene scaffolds. Canadian Journal of Chemistry 2017, 95, 975–983. doi:10.1139/cjc-2017-0220
  • Pifferi, C.; Daskhan, G. C.; Fiore, M.; Shiao, T. C.; Roy, R.; Renaudet, O. Aminooxylated Carbohydrates: Synthesis and Applications. Chemical reviews 2017, 117, 9839–9873. doi:10.1021/acs.chemrev.6b00733
  • Mellet, C. O.; Nierengarten, J.-F.; Fernández, J. M. G. Multivalency as an action principle in multimodal lectin recognition and glycosidase inhibition: a paradigm shift driven by carbon-based glyconanomaterials. Journal of materials chemistry. B 2017, 5, 6428–6436. doi:10.1039/c7tb00860k
  • García-Moreno, M. I.; Ortega-Caballero, F.; Rísquez-Cuadro, R.; Mellet, C. O.; Fernández, J. M. G. The Impact of Heteromultivalency in Lectin Recognition and Glycosidase Inhibition: An Integrated Mechanistic Study. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 6295–6304. doi:10.1002/chem.201700470
  • Bagul, R. S.; Hosseini, M. M.; Shiao, T. C.; Saadeh, N. K.; Roy, R. Heterolayered hybrid dendrimers with optimized sugar head groups for enhancing carbohydrate–protein interactions. Polymer Chemistry 2017, 8, 5354–5366. doi:10.1039/c7py01044c
  • Daskhan, G. C.; Pifferi, C.; Renaudet, O. Synthesis of a New Series of Sialylated Homo‐ and Heterovalent Glycoclusters by using Orthogonal Ligations. ChemistryOpen 2016, 5, 477–484. doi:10.1002/open.201600062
  • Müller, C.; Despras, G.; Lindhorst, T. K. Organizing multivalency in carbohydrate recognition. Chemical Society reviews 2016, 45, 3275–3302. doi:10.1039/c6cs00165c
  • Vincent, S. P.; Buffet, K.; Nierengarten, I.; Imberty, A.; Nierengarten, J.-F. Biologically Active Heteroglycoclusters Constructed on a Pillar[5]arene-Containing [2]Rotaxane Scaffold. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 22, 88–92. doi:10.1002/chem.201504110
  • Thomas, B.; Pifferi, C.; Daskhan, G. C.; Fiore, M.; Berthet, N.; Renaudet, O. Divergent and convergent synthesis of GalNAc-conjugated dendrimers using dual orthogonal ligations. Organic & biomolecular chemistry 2015, 13, 11529–11538. doi:10.1039/c5ob01870f
  • Meyer, A.; Noël, M.; Vasseur, J.-J.; Morvan, F. Hetero-Click Conjugation of Oligonucleotides with Glycosides Using Bifunctional Phosphoramidites. European Journal of Organic Chemistry 2015, 2015, 2921–2927. doi:10.1002/ejoc.201500165
  • Lindhorst, T. K. Multivalent glycosystems for nanoscience. Beilstein journal of organic chemistry 2014, 10, 2345–2347. doi:10.3762/bjoc.10.244
  • Daskhan, G. C.; Berthet, N.; Thomas, B.; Fiore, M.; Renaudet, O. Multivalent glycocyclopeptides: toward nano-sized glycostructures. Carbohydrate research 2014, 405, 13–22. doi:10.1016/j.carres.2014.07.017
  • Fiore, M.; Daskhan, G. C.; Thomas, B.; Renaudet, O. Orthogonal dual thiol-chloroacetyl and thiol-ene couplings for the sequential one-pot assembly of heteroglycoclusters. Beilstein journal of organic chemistry 2014, 10, 1557–1563. doi:10.3762/bjoc.10.160
Other Beilstein-Institut Open Science Activities