Literature DB >> 34165284

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

Anand K Agrahari1, Priyanka Bose1, Manoj K Jaiswal1, Sanchayita Rajkhowa2, Anoop S Singh1, Srinivas Hotha3, Nidhi Mishra1, Vinod K Tiwari1.   

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.

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Year:  2021        PMID: 34165284     DOI: 10.1021/acs.chemrev.0c00920

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  9 in total

1.  Aza-Oxa-Triazole Based Macrocycles with Tunable Properties: Design, Synthesis, and Bioactivity.

Authors:  Subba Rao Cheekatla; Liya Thurakkal; Anna Jose; Debashis Barik; Mintu Porel
Journal:  Molecules       Date:  2022-05-25       Impact factor: 4.927

2.  Synthesis of Xylan-Click-Quaternized Chitosan via Click Chemistry and Its Application in the Preparation of Nanometal Materials.

Authors:  Yuqiong Luo; Jihai Cai; Yanan Huang; Jiwen Luo
Journal:  Molecules       Date:  2022-05-27       Impact factor: 4.927

3.  Ag2O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones.

Authors:  Hua-Feng He; Yuwan Wang; Chun Zou; Zheng Tu; Yongquan Xu; Junfeng Yin
Journal:  ACS Omega       Date:  2022-01-11

4.  Terminal and Internal Alkyne Complexes and Azide-Alkyne Cycloaddition Chemistry of Copper(I) Supported by a Fluorinated Bis(pyrazolyl)borate.

Authors:  Anurag Noonikara-Poyil; Alvaro Muñoz-Castro; H V Rasika Dias
Journal:  Molecules       Date:  2021-12-21       Impact factor: 4.411

5.  Extracellular Electron Transfer Enables Cellular Control of Cu(I)-Catalyzed Alkyne-Azide Cycloaddition.

Authors:  Gina Partipilo; Austin J Graham; Brian Belardi; Benjamin K Keitz
Journal:  ACS Cent Sci       Date:  2022-01-14       Impact factor: 18.728

6.  Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase.

Authors:  Peterson de Andrade; Sanaz Ahmadipour; Robert A Field
Journal:  Beilstein J Org Chem       Date:  2022-02-17       Impact factor: 2.883

7.  Targeting Multiresistant Gram-Positive Bacteria by Ruthenium, Osmium, Iridium and Rhodium Half-Sandwich Type Complexes With Bidentate Monosaccharide Ligands.

Authors:  Bence Balázs; Zoltán Tóth; István Kacsir; Adrienn Sipos; Péter Buglyó; László Somsák; Éva Bokor; Gábor Kardos; Péter Bai
Journal:  Front Chem       Date:  2022-04-12       Impact factor: 5.545

Review 8.  Synthesis and Application of Trehalose Materials.

Authors:  Daniele Vinciguerra; Madeline B Gelb; Heather D Maynard
Journal:  JACS Au       Date:  2022-07-06

9.  The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives.

Authors:  Josip Požar; Marija Cvetnić; Andrea Usenik; Nikola Cindro; Gordan Horvat; Katarina Leko; Matija Modrušan; Vladislav Tomišić
Journal:  Molecules       Date:  2022-01-12       Impact factor: 4.411

  9 in total

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