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Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications.

Authors :
Agrahari AK
Bose P
Jaiswal MK
Rajkhowa S
Singh AS
Hotha S
Mishra N
Tiwari VK
Source :
Chemical reviews [Chem Rev] 2021 Jul 14; Vol. 121 (13), pp. 7638-7956. Date of Electronic Publication: 2021 Jun 24.
Publication Year :
2021

Abstract

Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

Details

Language :
English
ISSN :
1520-6890
Volume :
121
Issue :
13
Database :
MEDLINE
Journal :
Chemical reviews
Publication Type :
Academic Journal
Accession number :
34165284
Full Text :
https://doi.org/10.1021/acs.chemrev.0c00920