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
相关论文
共 1333 条
  • [61] A new chemical probe for proteomics of carbohydrate-binding proteins
    Ballell, L
    Alink, KJ
    Slijper, M
    Versluis, C
    Liskamp, RMJ
    Pieters, RJ
    [J]. CHEMBIOCHEM, 2005, 6 (02) : 291 - 295
  • [62] A new chemical probe for the detection of the cancer-linked galectin-3
    Ballell, Lluis
    van Scherpenzeel, Monique
    Buchalova, Katerina
    Liskamp, Rob M. J.
    Pieters, Roland J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) : 4387 - 4394
  • [63] [2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOLE-2'',2''-DIOXIDE) (TSAO) DERIVATIVES OF PURINE AND PYRIMIDINE NUCLEOSIDES AS POTENT AND SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1
    BALZARINI, J
    PEREZPEREZ, MJ
    SANFELIX, A
    VELAZQUEZ, S
    CAMARASA, MJ
    DECLERCQ, E
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (05) : 1073 - 1080
  • [64] Multivalent Display and Receptor-Mediated Endocytosis of Transferrin on Virus-Like Particles
    Banerjee, Deboshri
    Liu, Allen P.
    Voss, Neil R.
    Schmid, Sandra L.
    Finn, M. G.
    [J]. CHEMBIOCHEM, 2010, 11 (09) : 1273 - 1279
  • [65] Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents
    Banerjee, Swagata
    Veale, Emma B.
    Phelan, Caroline M.
    Murphy, Samantha A.
    Tocci, Gillian M.
    Gillespie, Lisa J.
    Frimannsson, Daniel O.
    Kelly, John M.
    Gunnlaugsson, Thorfinnur
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (04) : 1601 - 1618
  • [66] CRYSTAL-STRUCTURE OF HUMAN PROTEIN-TYROSINE-PHOSPHATASE 1B
    BARFORD, D
    FLINT, AJ
    TONKS, NK
    [J]. SCIENCE, 1994, 263 (5152) : 1397 - 1404
  • [67] Click glycoconjugation of per-azido- and alkynyl-functionalized β-peptides built from aspartic acid
    Barra, Marielle
    Roy, Olivier
    Traikia, Mounir
    Taillefumier, Claude
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) : 2941 - 2955
  • [68] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis
    Baudequin, C
    Brégeon, D
    Levillain, J
    Guillen, F
    Plaquevent, JC
    Gaumont, AC
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (24) : 3921 - 3945
  • [69] Design and synthesis of new carbohydrate-lithocholic acid conjugates linked via 1,2,3-triazole rings
    Bautista-Hernandez, Claudia I.
    Negron-Silva, Guillermo E.
    Santillan, Rosa
    Ivonne Vergara-Arenas, Blanca
    Angeles-Beltran, Deyanira
    Lomas-Romero, Leticia
    Perez-Martinez, Diego
    [J]. TETRAHEDRON, 2018, 74 (16) : 2009 - 2019
  • [70] Chemoselective Ligation in the Functionalization of Polysaccharide-Based Particles
    Beaudette, Tristan T.
    Cohen, Joel A.
    Bachelder, Eric M.
    Broaders, Kyle E.
    Cohen, Jessica L.
    Engleman, Edgar G.
    Frechet, Jean M. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) : 10360 - +