Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Abstract

Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review

“…This displacement of two axial N2 atoms from the basal plane formed by two pyridine N4 atoms and two chloride ions leads to a pyramidal distortion of the octahedral geometry. In another reported ionic complex of [Cu(L1) 2 (CH 3 CN)-(ClO 4 )](ClO 4 ), 176 the copper cation displays the square-planar geometry of four nitrogen atoms with CH 3 CN and ClO 4 À ligands at the axial positions.…”

“…The crystal structure and DFT calculated structural data for [Cu 2 Pt 2 (L) 4 ] 6+ complexes demonstrated their tetrahedral geometry, 129,177,179 but only using the asymmetric ligands with orthogonal binding sites in combination with cis-protecting directional bonding strategies at the Pt(II) centers.…”

<strong>CATALYSIS INVESTIGATION FOR SYNTHESIS OF 2-AMINO-4<em>H</em>-PYRAN-3-CARBONITRILES CONTAINING PROPARGYL GROUP</strong>

“…In continuation of our work, herein a green approach for the one pot synthesis of propargyl ester of 2-amino-3-cyano-4H-pyran derivatives has been reported. These esters will be used in our further research in click reaction with tetra-O-acetyl-β-D-glucopyranosyl azide [6,7].…”

Synthesis and evaluation of a water-solubility glycosyl-rhodamine fluorescent probe detecting Hg2+

“…The glucose molecule had been even used to improve the water-solubility of fluorescent probe via incorporating D-glucosamine group and quinoline group 25 . Inspired by these, in this work we introduced three glucose units into rhodamine framework via click reaction technology, which has been widely used to construct complex architectures in carbohydrate chemistry 26 , to increase the water-solubility of rhodamine molecule, and broaden its application for the detection of Hg 2+ ion in the water-solubility environment and biological systems. The obtained target compound (RBGlc-3) to detect Hg 2+ ion was correspondingly characterized and evaluated in the water-solubility environment.…”