Download PDF
Rutjes, F. P. J. T. : 2022 Science of Synthesis, 2021/4: Click Chemistry DOI: 10.1055/sos-SD-235-00078
Click Chemistry

2.4 CuAAC in Carbohydrate Conjugation

More Information

Book

Editor: Rutjes, F. P. J. T. 

Authors: Agrahari, A. K.; Alabugin, I. V. ; Beke-Somfai, T. ; Blanco-Ania, D. ; Bratlie, K. M. ; Carlson, J. C. T. ; Friscourt, F. ; Giel, M.-C. ; Harris, T. ; Houk, K. N. ; Janssen, L. J. N.; Kacprzak, K. M.; Kann, N. ; Kovalová, A.; Kuba, W. ; La Venia, A.; Liskamp, R. M. J. ; Meuleman, T. J.; Mikula, H. ; Mishra, A.; Moses, J. E. ; Ort, F. F.; Page, K. M.; Paterson, A. J. ; Rutkowski, J.; Singh, R.; Sinha, A. K.; Skiera, I.; Smedley, C. J. ; Svatunek, D. ; Tiwari, V. K. ; van Hest, J. C. M. ; Vrabel, M. ; Wilkovitsch, M. ; Xu, Z.; Zhang, C.

Title: Click Chemistry

Print ISBN: 9783132435568; Online ISBN: 9783132435575; Book DOI: 10.1055/b000000077

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

Copper(I)-catalyzed azide–alkyne cycloaddition reactions (CuAAC), as a versatile, reliable, and modular strategy, have been widely investigated in the area of glycoscience during the last 20 years. Herein, we presented a brief overview of CuAAC click approaches for easy access to diverse simple and complex triazole-appended carbohydrate-containing molecular architectures. Both intermolecular and intramolecular CuAAC conjugation of glycosylated azides and terminal alkynes have been widely employed for the regioselective triazole-forming reaction under standard click conditions.

Key words

click chemistry - copper-catalyzed azide–alkyne cycloaddition (CuAAC) - alkynes - azides - copper catalysis - triazoles - carbohydrates - conjugation
 
  • 1 Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X. Chem. Rev.. 2016; 116: 3086
    Google Scholar
  • 2 Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA. Med. Res. Rev.. 2008; 2: 278
    Google Scholar
  • 3 Huisgen R. Angew. Chem. Int. Ed. Engl.. 1963; 2: 565
    Google Scholar
  • 4 Tornøe CW, Christensen C, Meldal M. J. Org. Chem.. 2002; 67: 3057
    Google Scholar
  • 5 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed.. 2002; 41: 2596
    Google Scholar
  • 6 Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc.. 2005; 127: 15998
    Google Scholar
  • 7 Thirumurugan P, Matosiuk D, Jozwiak K. Chem. Rev.. 2013; 113: 4905
    Google Scholar
  • 8 Carbohydrates in Drug Discovery and Development. Tiwari VK. Elsevier; Amsterdam 2020
    Google Scholar
  • 11 Mishra N, Agrahari AK, Bose P, Singh SK, Singh AS, Tiwari VK. Sci. Rep.. 2020; 10: 3586
    Google Scholar
  • 12 Akula RA, Temelkoff DP, Artis ND, Norris P. Heterocycles. 2004; 63: 2719
    Google Scholar
  • 13 Chennaiah A, Bhowmick S, Vankar YD. RSC Adv.. 2017; 7: 41755
    Google Scholar
  • 14 Dedola S, Hughes DL, Nepogodiev SA, Rejzek M, Field RA. Carbohydr. Res.. 2010; 345: 1123
    Google Scholar
  • 15 Carvalho I, Andrade P, Campo VL, Guedes PMM, Sesti-Costa R, Silva JS, Schenkman S, Dedola S, Hill L, Rejzek M, Nepogodiev SA, Field RA. Bioorg. Med. Chem.. 2010; 18: 2412
    Google Scholar
  • 16 Mishra KB, Tiwari VK. J. Org. Chem.. 2014; 79: 5752
    Google Scholar
  • 17 Kumar D, Mishra KB, Mishra BB, Mondal S, Tiwari VK. Steroids. 2014; 80: 71
    Google Scholar
  • 18 Mishra KB, Mishra BB, Tiwari VK. Carbohydr. Res.. 2014; 399: 2
    Google Scholar
  • 19 Bautista-Hernández CI, Negrón-Silva GE, Santillán R, Vergara-Arenas BI, Ángeles-Beltrán D, Lomas-Romero L, Pérez-Martínez D. Tetrahedron. 2018; 74: 2009
    Google Scholar
  • 20 Mishra KB, Tiwari N, Bose P, Singh R, Rawat AK, Singh SK, Mishra RC, Singh RK, Tiwari VK. ChemistrySelect. 2019; 4: 2644
    Google Scholar
  • 21 Dwivedi P, Mishra KB, Mishra BB, Singh N, Singh RK, Tiwari VK. Glycoconjugate J.. 2015; 32: 127
    Google Scholar
  • 22 Olomola TO, Klein R, Mautsa N, Sayed Y, Kaye PT. Bioorg. Med. Chem.. 2013; 21: 1964 Bioorg. Med. Chem.. 2013; 21: 6856
    Google Scholar
  • 23 Palomo C, Aizpurua JM, Balentová E, Azcune I, Santos JI, Jiménez-Barbero J, Cañada J, Miranda JI. Org. Lett.. 2008; 10: 2227
    Google Scholar
  • 24 Hradilová L, Poláková M, Dvořáková B, Hajdúch M, Petruš L. Carbohydr. Res.. 2012; 361: 1
    Google Scholar
  • 25 Yang J.-W, He X.-P, Li C, Gao L.-X, Sheng L, Xie J, Shi X.-X, Tang Y, Li J, Chen G.-R. Bioorg. Med. Chem. Lett.. 2011; 21: 1092
    Google Scholar
  • 26 Martin H, McGovern M, Abbey L, Gilroy A, Mullins S, Howell S, Kavanagh K, Velasco-Torrijos T. Eur. J. Med. Chem.. 2018; 160: 82
    Google Scholar
  • 27 Agrahari AK, Singh AS, Singh AK, Mishra N, Singh M, Prakas P, Tiwari VK. New J. Chem.. 2019; 43: 12475
    Google Scholar
  • 29 Fiore M, Chambery A, Marra A, Dondoni A. Org. Biomol. Chem.. 2009; 7: 3910
    Google Scholar
  • 30 Papin C, Doisneau G, Beau J.-M. Chem.–Eur. J.. 2009; 15: 53
    Google Scholar
  • 31 Diot J, García-Moreno MI, Gouin SG, Mellet CO, Haupt K, Kovensky J. Org. Biomol. Chem.. 2009; 7: 357
    Google Scholar
  • 32 Carmona AT, Carrión-Jiménez S, Pingitore V, Moreno-Clavijo E, Robina I, Moreno-Vargas AJ. Eur. J. Med. Chem.. 2018; 151: 765
    Google Scholar
  • 33 Cheng K, Liu J, Liu X, Li H, Sun H, Xie J. Carbohydr. Res.. 2009; 344: 841
    Google Scholar
  • 34 Cheng K, Liu J, Sun H, Bokor , Czifrák K, Kónya B, Tóth M, Docsa T, Gergely P, Somsák L. New J. Chem.. 2010; 34: 1450
    Google Scholar
  • 35 Mishra A, Tiwari VK. J. Org. Chem.. 2015; 80: 4869
    Google Scholar
  • 36 Zhang Y.-H, Zhang Y.-M, Chen Y, Yang Y, Liu Y. Org. Chem. Front.. 2014; 1: 355
    Google Scholar
  • 37 Mishra A, Tiwari VK. ChemistrySelect. 2017; 2: 9466
    Google Scholar
  • 38 Casas-Solvas JM, Ortiz-Salmerón E, Giménez-Martínez J, García-Fuentes J, Capitán-Vallvey LF, Santoyo-González F, Vargas-Berenguel A. Chem.–Eur. J.. 2009; 15: 710
    Google Scholar
  • 39 Droumaguet LC, Wang C, Wang Q. Chem. Soc. Rev.. 2010; 39: 1233
    Google Scholar
  • 40 Kushwaha D, Singh RS, Tiwari VK. Tetrahedron Lett.. 2014; 55: 4532
    Google Scholar
  • 41 Ivanova IN, Nepogodiev SA, Saalbach G, OʼNeill EC, Urbaniak MD, Ferguson MAJ, Gurcha SS, Besra GS, Field RA. Carbohydr. Res.. 2017; 438: 26
    Google Scholar
  • 42 Thakur A, Mandal D, Deb P, Mondal B, Ghosh S. RSC Adv.. 2014; 4: 1918
    Google Scholar
  • 43 Dolai B, Nayim S, Hossain M, Pahari P, Atta AK. Sens. Actuators, B. 2019; 279: 476
    Google Scholar
  • 44 Nongbe MC, Bretel G, Ekou L, Ekou T, Robitzer M, Le Grognec E, Felpin F.-X. Cellulose. 2018; 25: 1395
    Google Scholar
  • 45 Hassane FS, Frisch B, Schuber F. Bioconjugate Chem.. 2006; 17: 849
    Google Scholar
  • 46 Zerkowski JA, Nuñez A, Strahan GD, Solaiman DKY. J. Am. Oil Chem. Soc.. 2009; 86: 1115
    Google Scholar
  • 47 Tyagi M, Kartha KPR. Carbohydr. Res.. 2015; 413: 85
    Google Scholar
  • 48 Pérez-Labrada K, Brouard I, Méndez I, Pérez CS, Gavín JA, Rivera DG. Eur. J. Org. Chem.. 2014; 3671
    Google Scholar
  • 49 Rabuka D, Hubbard SC, Laughlin ST, Argade SP, Bertozzi CR. J. Am. Chem. Soc.. 2006; 128: 12078
    Google Scholar
  • 50 Webler CB, Jiang H, Wang W, Baughn AD, Wu P. Bioorg. Med. Chem. Lett.. 2011; 21: 4989
    Google Scholar
  • 51 Gupta SS, Kuzelka J, Singh P, Lewis WG, Manchester M, Finn MG. Bioconjugate Chem.. 2005; 16: 1572
    Google Scholar
  • 52 Gupta SS, Raja KS, Kaltgrad E, Strable E, Finn MG. Chem. Commun. (Cambridge). 2005; 4315
    Google Scholar
  • 53 Sawa M, Hsu T.-L, Itoh T, Sugiyama M, Hanson SR, Vogt PK, Wong C.-H. Proc. Natl. Acad. Sci. U. S. A.. 2006; 103: 12371
    Google Scholar
  • 54 Astronomo RD, Kaltgrad E, Udit AK, Wang S.-K, Doores KJ, Huang C.-Y, Pantophlet R, Paulson JC, Wong C.-H, Finn MG, Burton DR. Chem. Biol.. 2010; 17: 357
    Google Scholar
  • 56 Mindt TL, Struthers H, Brans L, Anguelov T, Schweinsberg C, Maes V, Tourwé D, Schibli R. J. Am. Chem. Soc.. 2006; 128: 15096
    Google Scholar
  • 57 Fernández S, Croëcamo N, Incerti M, Giglio J, Scarone L, Rey A. J. Labelled Compd. Radiopharm.. 2012; 55: 274
    Google Scholar
  • 58 Kizaka-Kondoh S, Konse-Nagasawa H. Cancer Sci.. 2009; 100: 1366
    Google Scholar
  • 59 Fernández S, Giglio J, Rey AM, Cerecetto H. Bioorg. Med. Chem.. 2012; 20: 4040
    Google Scholar
  • 60 Jung K.-H, Müller M, Schmidt RR. Chem. Rev.. 2000; 100: 4423
    Google Scholar
  • 61 Tiwari VK, Kumar A, Schmidt RR. Eur. J. Org. Chem.. 2012; 2945
    Google Scholar
  • 63 Ray A, Manoj K, Bhadbhade MM, Mukhopadhyay R, Bhattacharjya A. Tetrahedron Lett.. 2006; 47: 2775
    Google Scholar
  • 64 Chandrasekhar S, Rao CL, Nagesh C, Reddy CR, Sridhar B. Tetrahedron Lett.. 2007; 48: 5869
    Google Scholar
  • 66 Chen A, Samankumara LP, Dodlapati S, Wang D, Adhikari S, Wang G. Eur. J. Org. Chem.. 2019; 1189
    Google Scholar
  • 67 Bodine KD, Gin DY, Gin MS. Org. Lett.. 2005; 7: 4479
    Google Scholar
  • 68 Bodine KD, Gin DY, Gin MS. J. Am. Chem. Soc.. 2004; 126: 1638
    Google Scholar
  • 69 Campo VL, Carvalho I, Da Silva CHTP, Schenkman S, Hill L, Nepogodiev SA, Field RA. Chem. Sci.. 2010; 1: 507
    Google Scholar
  • 70 Cheng J, Yu H, Lau K, Huang S, Chokhawala HA, Li Y, Tiwari VK, Chen X. Glycobiology. 2008; 18: 686
    Google Scholar
  • 71 Muthana S, Yu H, Cao H, Cheng J, Chen X. J. Org. Chem.. 2009; 74: 2928
    Google Scholar