Synthesis of glycoconjugate mimics by ‘click chemistry’

Thakur, Kratima; Khare, Naveen K.

doi:10.1016/j.carres.2019.107775

Cited by 6 publications

(3 citation statements)

References 36 publications

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“…Recently, Thakur and Khare reported a convenient and high-yield protocol for easy access to a library comprising glycoconjugate mimics by reacting 2-deoxy propargyl glycosides with β-glycopyranosylazides in the presence of CuI in acetonitrile. Although the method produced excellent reaction yield and avoided use of any base, high loading of catalyst (2.5 equiv of CuI) is required to provide the 94% optimized yield . In addition, this modular CuAAC click chemistry has been widely explored with a number of highly demanding scaffolds, including 4-(2-chloroethoxy)phenyl glycosides as Janus aglycons, triazole-linked 1,3,4-oxadiazole glycoconjugates, and triazole-appended bis-glycoconjugates .…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

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

et al. 2021

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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.

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Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

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

et al. 2021

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“…In 2001, Sharpless and his co-workers introduced the concept of “click chemistry” to describe “spring-loaded” exothermic reactions that are versatile and modular, give high yields, and do not generate harmful by-products [ 22 ]. The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between terminal alkynes and azides has become the most widely used click chemistry reaction in the past two decades [ 23 , 24 , 25 ]. Although click chemistry reactions were originally designed to facilitate low-molecular-weight drug discovery, they are now used in broad areas of chemistry, such as material sciences [ 26 , 27 ], nanotechnology [ 28 , 29 ], and the bioconjugation and modification of DNA, natural products, and polymers [ 30 , 31 ].…”

Section: Introductionmentioning

confidence: 99%

Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity

Rathinam,

Magdadaro,

Hjálmarsdóttir

et al. 2024

JFB

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The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against S. aureus, E. faecalis, E. coli, and P. aeruginosa. The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria.

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“…To achieve the combination of PEO and β-CD, the click reaction, as a robust reaction without side reactions or tedious purification process, [18][19][20][21] was applied. From previous researches, it can be found that N 3 -β-CD is a common kind of β-CD derivative.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and performance of a novel polycarboxylate superplasticizer through grafting the β‐cyclodextrin on the side chain by click reaction

Gao

Wang

2021

J of Applied Polymer Sci

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A novel monovinyl β-cyclodextrin monomer (β-P) is employed to synthesize polycarboxylate superplasticizers with β-cyclodextrin (β-CD) grafted on the end of side chain [PAA-g-(β-P) n HPEG, n is the mass ratio of β-P in macromonomer, n = 3%~9%]. β-P is synthesized through grafting β-CD on the polyoxyethylene (PEO) via click reaction, which is the first try to superimpose the steric hindrance effect of PEO and β-CD during the preparation of polycarboxylate superplasticizer. FTIR, 1 H NMR, GPC, and DLS are used to characterize the molecular structure of the intermediates and the products.Compared with PAA-g-HPEG (PCE0) only with PEO as side chains, cement paste containing PAA-g-(β-P) 7% HPEG has the largest fluidity; PAA-g-(β-P) 9% HPEG corresponds to the best fluidity retention performance; cement paste containing PAA-g-(β-P) n HPEG has shorter setting time. The DLS results reveal that the introduction of β-CD in PAA-g-(β-P) n HPEG extends the side chain length and increases the steric hindrance effect. The adsorption test results show that the novel PCE has good slump retention performance because it is adsorbed on cement particles less but more lives in the liquid phase with the n increasing. This study provides a new approach to synthesize high-performance polycarboxylate superplasticizer.

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Synthesis of glycoconjugate mimics by ‘click chemistry’

Cited by 6 publications

References 36 publications

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

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

Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity

Synthesis and performance of a novel polycarboxylate superplasticizer through grafting the β‐cyclodextrin on the side chain by click reaction

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