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

被引:269
作者
Agrahari, Anand K. [1 ]
Bose, Priyanka [1 ]
Jaiswal, Manoj K. [1 ]
Rajkhowa, Sanchayita [2 ]
Singh, Anoop S. [1 ]
Hotha, Srinivas [3 ]
Mishra, Nidhi [1 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[2] Jorhat Inst Sci & Technol JIST, Dept Chem, Jorhat 785010, Assam, India
[3] Indian Inst Sci & Engn Res IISER, Dept Chem, Pune 411021, Maharashtra, India
关键词
AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; CARBOHYDRATE-PROTEIN INTERACTIONS; PERYLENEDIIMIDE-BASED GLYCOCLUSTERS; CENTERED MULTIVALENT GLYCOCLUSTERS; RUTHENIUM-CATALYZED CYCLOADDITION; DECARBOXYLATIVE MANNICH REACTION; CARBONIC-ANHYDRASE INHIBITORS; RING-OPENING POLYMERIZATION; PROMOTED CONJUGATE ADDITION;
D O I
10.1021/acs.chemrev.0c00920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:7638 / 7955
页数:318
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