The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Recent applications of thiol–ene coupling as a click process for glycoconjugation
Abstract
There has been over the past decades a resurgence of the free-radical thiol-ene coupling (TEC) as a method for assembling crosslinked networks and polymer functionalization. On the other hand the use of TEC in carbohydrate chemistry, a field of special importance due to the key role of carbohydrates in living organisms, is represented only by a handful of papers. Nevertheless it appears that TEC possesses many if not all the attributes of a click process proceeding with the assistance of the greenest catalyst such as visible light. This tutorial review focuses on the application of TEC on different topics, all related to glycochemistry, including: (a) carbohydrate modification, (b) oligosaccharide and glycosyl amino acid synthesis, (c) assembly of glycoclusters on rigid molecular platforms (calixarene, cyclodextrin, silsesquioxane, dendrimer), (d) peptide and protein glycosylation. Also the very recent development in peptide glycosylation by the closely related thiol-yne chemistry is described.
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Citations
Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Introduction and General Overview of Cyclodextrin Chemistry
Szejtli, J. (1998) · Chemical Reviews · doi:10.1021/cr970022c · Cited by 5,016
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis
Lowe, A. B. (2010) · Polym. Chem. · doi:10.1039/b9py00216b · Cited by 1,563
Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling
Fiore, M., Lo Conte, M., Pacifico, S., Marra, A., & Dondoni, A. (2011) · Tetrahedron Letters · doi:10.1016/j.tetlet.2010.11.097 · Cited by 38
Self-citation
Cited by
Thiyl Radicals in Organic Synthesis
Dénès, F., Pichowicz, M., Povie, G., & Renaud, P. (2014) · Chemical Reviews · doi:10.1021/cr400441m · Cited by 985
Lowe, A. B. (2014) · Polym. Chem. · doi:10.1039/c4py00339j · Cited by 768
Glycomimetics versus Multivalent Glycoconjugates for the Design of High Affinity Lectin Ligands
Cecioni, S., Imberty, A., & Vidal, S. (2015) · Chemical Reviews · doi:10.1021/cr500303t · Cited by 544
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Metadata
- Authors
- Dondoni, A., & Marra, A.
- Venue
- Chem. Soc. Rev.
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2012
- Volume
- 41
- Issue
- 2
- Pages
- 573-586
- ISSN
- 0306-0012 (ISSN-L)
- 1460-4744
- OpenAlex
- W2050213698
- Cited by
- 293
- References
- 4
- FWCI
- 0.69
- Type
- journal article
- Language
- en
- Open access
- closed
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