Development of sustainable synthesis of glucuronic acid glycodendrimers using ball milling and microwave-assisted CuAAC reaction

Abstract

Two green strategies for the copper-catalyzed azide-alkyne cycloaddition reaction (CuAAC) based on two different activation pathways, solvent free mechanochemistry and microwave irradiation (MW) using biomass-derived solvents, are reported for the...

Copper(i)-catalyzed click chemistry in deep eutectic solvent for the syntheses of β-d-glucopyranosyltriazoles

“…The click reaction in glyco-chemistry have already been explored and the reaction is performed in various hazardous organic solvents such as toluene, DCM, acetonitrile, DMF and THF. [46][47][48][49][50][51][52][53][54][55][56][57][58][86][87][88][89][90][91][92][93][94][95][96] Herein, for the rst time, we studied the use of deep eutectic solvents (DESs) as reaction media for the syntheses of triazolyl glycoconjugates. In our present work, a series of DESs were prepared through the combination of various hydrogen-bond acceptor such as choline chloride (ChCl), tetra butyl ammonium bromide (TBAB), tetramethyl ammonium chloride (TMAC) and methyl triphenyl phosphonium bromide (MTPB) and various hydrogen bond donors, namely urea, thiourea, glycerol and ethylene glycol.…”

“…[29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] Along with the successful development of CuAAC reactions in various elds of chemistry, its application in carbohydrate chemistry has been parallelly explored. [46][47][48][49][50][51][52][53][54][55][56][57][58] In this regard, Tiwari and co-workers elegantly illustrated the application of click chemistry in glycoscience. 46,47 Carbohydrates are very common class of biomolecules and an integral part of living cells.…”

“…69 These glycoproducts have widespread applications including medicinal science, material science, gelation, chelation, sensing, glycosylation, phermacology and catalysis. [46][47][48][49][50][51][52][53][54][55][56][57][58] However, sustainable synthetic approach of this modular and bio-orthogonal clickcarbohydrate chemistry is less explored.…”

Exploring Rigid and Flexible Scaffolds to Develop Potent Glucuronic Acid Glycodendrimers for Dengue Virus Inhibition

“…The CuAAC reaction has proven to be extremely useful in the synthesis of GDs due to the comparatively very facile functionalization of organic scaffolds with azides and alkynes, which remain unaffected throughout the subsequent transformations in the presence of highly functionalized biomolecules. ,, The CuAAC reaction presents several advantages because this reaction is simple to perform, modular, wide scope, highly efficient, high yielding, and regiospecific, requires readily available alkynes/azides as starting materials and reagents such as copper catalysts, and is conducted in easily removable or benign solvents (e.g., H 2 O or biosolvent). , Based on our previous results and with the intention of increasing the affinity of the glycodendrons toward the DENV envelope protein, three new sets of GlcA-based dendrimers bearing different levels of multivalency, polarity, and structural features were designed for affinity binding assays. Their chemical synthesis was performed sequentially in three stages, namely, (a) the chemical synthesis of the oligoalkynyl scaffolds, (b) assembling with fully protected GlcA-based azide units by using a microwave (MW)-assisted CuAAC protocol, and (c) sequential deprotection of hydroxyl and carboxylic acid groups (Scheme ).…”

“…In recent decades, there have been increasing efforts to design and synthesize GDs that could interfere with bacterial and viral infections, suggesting the feasibility of antiadhesive therapy for infectious diseases and the potential of multivalent carbohydrates in this context. ,− The number of publications has significantly increased, and many potent antiadhesive glycoclusters, including glycodendrons and GDs, have been proposed. Our research group was the first to report an efficient and sustainable copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC) for the synthesis of novel GlcA glycodendrons as potential active compounds in the treatment of DENV. Our previous work described the preparation of a tetravalent GlcA dendron that binds with good affinity to the DENV envelope protein ( K D = 22 μM) .…”