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Rutjes, F. P. J. T. : 2022 Science of Synthesis, 2021/4: Click Chemistry DOI: 10.1055/sos-SD-235-00062
Click Chemistry

2.3 CuAAC in Protein Conjugation

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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

This chapter summarizes the use of the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction in the synthesis of peptide and protein conjugates. The different reaction conditions used for construction of the conjugates and their application in various disciplines are covered. Synthetic strategies for the introduction of the click groups (azide or alkyne) into the peptide backbones are included as well.

Key words

click chemistry - copper-catalyzed azide–alkyne cycloaddition (CuAAC) - alkynes - azides - copper catalysts - dipolar cycloadditions - peptide modification - protein modification - triazoles
 
  • 1 Adusumalli SR, Rawale DG, Singh U, Tripathi P, Paul R, Kalra N, Mishra RK, Shukla S, Rai V. J. Am. Chem. Soc.. 2018; 140: 15114
    Google Scholar
  • 4 Miller LW, Cornish VW. Curr. Opin. Chem. Biol.. 2005; 9: 56
    Google Scholar
  • 5 Wanigasekara MSK, Huang X, Chakrabarty JK, Bugarin A, Chowdhury SM. ACS Omega. 2018; 3: 14229
    Google Scholar
  • 7 Basle E, Joubert N, Pucheault M. Chem. Biol.. 2010; 17: 213
    Google Scholar
  • 8 Zhang G, Zheng S, Liu H, Chen PR. Chem. Soc. Rev.. 2015; 44: 3405
    Google Scholar
  • 9 van Vught R, Pieters RJ, Breukink E. Comput. Struct. Biotechnol. J.. 2014; 9: e201 402 001
    Google Scholar
  • 10 Tamura T, Hamachi I. J. Am. Chem. Soc.. 2019; 141: 2782
    Google Scholar
  • 11 Boutureira O, Bernardes GJL. Chem. Rev.. 2015; 115: 2174
    Google Scholar
  • 12 Krall N, da Cruz FP, Boutureira O, Bernardes GJL. Nature Chem.. 2016; 8: 103
    Google Scholar
  • 13 Nischan N, Hackenberger CP. J. Org. Chem.. 2014; 79: 10727
    Google Scholar
  • 14 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed.. 2002; 41: 2596
    Google Scholar
  • 15 Tornøe CW, Christensen C, Meldal M. J. Org. Chem.. 2002; 67: 3057
    Google Scholar
  • 16 Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG. J. Am. Chem. Soc.. 2003; 125: 3192
    Google Scholar
  • 18 Apel K, Hirt H. Annu. Rev. Plant Biol.. 2004; 55: 373
    Google Scholar
  • 20 Ray PD, Huang B.-W, Tsuji Y. Cell. Signalling. 2012; 24: 981
    Google Scholar
  • 21 Bachi A, Dalle-Donne I, Scaloni A. Chem. Rev.. 2013; 113: 596
    Google Scholar
  • 22 Li S, Cai H, He J, Chen H, Lam S, Cai T, Zhu Z, Bark SJ, Cai C. Bioconjugate Chem.. 2016; 27: 2315
    Google Scholar
  • 23 Stadtman ER, Berlett BS. Drug Metab. Rev.. 1998; 30: 225
    Google Scholar
  • 24 Kumar A, Li K, Cai C. Chem. Commun. (Cambridge). 2011; 47: 3186
    Google Scholar
  • 25 Hong V, Presolski SI, Ma C, Finn MG. Angew. Chem. Int. Ed.. 2009; 48: 9879
    Google Scholar
  • 26 Hatit MZC, Reichenbach LF, Tobin JM, Vilela F, Burley GA, Watson AJB. Nat. Commun.. 2018; 9: 4021
    Google Scholar
  • 27 Kennedy DC, McKay CS, Legault MCB, Danielson DC, Blake JA, Pegoraro AF, Stolow A, Mester Z, Pezacki JP. J. Am. Chem. Soc.. 2011; 133: 17993
    Google Scholar
  • 28 Soriano del Amo D, Wang W, Jiang H, Besanceney C, Yan AC, Levy M, Liu Y, Marlow FL, Wu P. J. Am. Chem. Soc.. 2010; 132: 16893
    Google Scholar
  • 29 Besanceney-Webler C, Jiang H, Zheng T, Feng L, Soriano del Amo D, Wang W, Klivansky LM, Marlow FL, Liu Y, Wu P. Angew. Chem. Int. Ed.. 2011; 50: 8051
    Google Scholar
  • 30 Sen Gupta S, Kuzelka J, Singh P, Lewis WG, Manchester M, Finn MG. Bioconjugate Chem.. 2005; 16: 1572
    Google Scholar
  • 31 Agard NJ, Prescher JA, Bertozzi CR. J. Am. Chem. Soc.. 2005; 127: 11196
    Google Scholar
  • 32 Schoffelen S, Lambermon MHL, van Eldijk MB, van Hest JCM. Bioconjugate Chem.. 2008; 19: 1127
    Google Scholar
  • 34 Pretze M, Kuchar M, Bergmann R, Steinbach J, Pietzsch J, Mamat C. ChemMedChem. 2013; 8: 935
    Google Scholar
  • 35 Ramenda T, Kniess T, Bergmann R, Steinbach J, Wuest F. Chem. Commun. (Cambridge). 2009; 7521
    Google Scholar
  • 36 Pickens CJ, Johnson SN, Pressnall MM, Leon MA, Berkland CJ. Bioconjugate Chem.. 2018; 29: 686
    Google Scholar
  • 37 Ahmad Fuaad AAH, Azmi F, Skwarczynski M, Toth I. Molecules. 2013; 18: 13148
    Google Scholar
  • 38 Tang W, Becker ML. Chem. Soc. Rev.. 2014; 43: 7013
    Google Scholar
  • 39 Hoogstede FABM, Rutjes FPJT, Click Reactions in Organic Synthesis. Chandrasekaran S. Wiley-VCH; Weinheim, Germany 2016. 141.
    Google Scholar
  • 40 Castro V, Rodríguez H, Albericio F. ACS Comb. Sci.. 2016; 18: 1
    Google Scholar
  • 41 Miller N, Williams GM, Brimble MA. Org. Lett.. 2009; 11: 2409
    Google Scholar
  • 42 Yim CB, Boerman OC, de Visser M, de Jong M, Dechesne AC, Rijkers DTS, Liskamp RMJ. Bioconjugate Chem.. 2009; 20: 1323
    Google Scholar
  • 43 DʼErcole A, Sabatino G, Pacini L, Impresari E, Capecchi I, Papini AM, Rovero P. Pept. Sci. (Hoboken, NJ, U. S.). 2020; 112
    Google Scholar
  • 44 Chen Y.-X, Zhao L, Huang Z.-P, Zhao Y.-F, Li Y.-M. Bioorg. Med. Chem. Lett.. 2009; 19: 3775
    Google Scholar
  • 45 Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett.. 2004; 6: 2853
    Google Scholar
  • 46 Isidro-Llobet A, Álvarez M, Albericio F. Chem. Rev.. 2009; 109: 2455
    Google Scholar
  • 47 Carberry TP, Tarallo R, Falanga A, Finamore E, Galdiero M, Weck M, Galdiero S. Chem.–Eur. J.. 2012; 18: 13678
    Google Scholar
  • 48 Dutot L, Lécorché P, Burlina F, Marquant R, Point V, Sagan S, Chassaing G, Mallet JM, Lavielle S. J. Chem. Biol.. 2010; 3: 51
    Google Scholar
  • 49 Feni L, Parente S, Robert C, Gazzola S, Arosio D, Piarulli U, Neundorf I. Bioconjugate Chem.. 2019; 30: 2011
    Google Scholar
  • 50 Hintersteiner M, Kimmerlin T, Kalthoff F, Stoeckli M, Garavel G, Seifert JM, Meisner NC, Uhl V, Buehler C, Weidemann T, Auer M. Chem. Biol.. 2009; 16: 724
    Google Scholar
  • 51 Jølck RI, Berg RH, Andresen TL. Bioconjugate Chem.. 2010; 21: 807
    Google Scholar
  • 52 Cox N, Kintzing JR, Smith M, Grant GA, Cochran JR. Angew. Chem. Int. Ed.. 2016; 55: 9894
    Google Scholar
  • 53 Thoreau F, Vanwonterghem L, Henry M, Coll JL, Boturyn D. Org. Biomol. Chem.. 2018; 16: 4101
    Google Scholar
  • 54 Liu Q, Kistemaker HAV, Bhogaraju S, Dikic I, Overkleeft HS, van der Marel GA, Ovaa H, van der Heden van Noort GJ, Filippov DV. Angew. Chem. Int. Ed.. 2018; 57: 1659
    Google Scholar
  • 55 Kovalová A, Pohl R, Vrabel M. Org. Biomol. Chem.. 2018; 16: 5960
    Google Scholar
  • 56 Bock VD, Perciaccante R, Jansen TP, Hiemstra H, van Maarseveen JH. Org. Lett.. 2006; 8: 919
    Google Scholar
  • 57 Gopi H, Umashankara M, Pirrone V, LaLonde J, Madani N, Tuzer F, Baxter S, Zentner I, Cocklin S, Jawanda N, Miller SR, Schön A, Klein JC, Freire E, Krebs FC, Smith III AB, Sodroski J, Chaiken I. J. Med. Chem.. 2008; 51: 2638
    Google Scholar
  • 58 Gopi HN, Tirupula KC, Baxter S, Ajith S, Chaiken IM. ChemMedChem. 2006; 1: 54
    Google Scholar
  • 59 Lundquist JT, Pelletier JC. Org. Lett.. 2001; 3: 781
    Google Scholar
  • 60 Rijkers DTS, van Esse GW, Merkx R, Brouwer AJ, Jacobs HJF, Pieters RJ, Liskamp RMJ. Chem. Commun. (Cambridge). 2005; 4581
    Google Scholar
  • 61 van Dijk M, van Nostrum CF, Hennink WE, Rijkers DTS, Liskamp RMJ. Biomacromolecules. 2010; 11: 1608
    Google Scholar
  • 62 Xu W, Lau YH, Fischer G, Tan YS, Chattopadhyay A, de la Roche M, Hyvönen M, Verma C, Spring DR, Itzhaki LS. J. Am. Chem. Soc.. 2017; 139: 2245
    Google Scholar
  • 63 Rijkers DTS, van Vugt HHR, Jacobs HJF, Liskamp RMJ. Tetrahedron Lett.. 2002; 43: 3657
    Google Scholar
  • 64 Goddard-Borger ED, Stick RV. Org. Lett.. 2007; 9: 3797
    Google Scholar
  • 65 Goddard-Borger ED, Stick RV. Org. Lett.. 2011; 13: 2514
    Google Scholar
  • 66 Parrish B, Breitenkamp RB, Emrick T. J. Am. Chem. Soc.. 2005; 127: 7404
    Google Scholar
  • 67 Sun H, Liu L, Lu J, Qiu S, Yang C.-Y, Yi H, Wang S. Bioorg. Med. Chem. Lett.. 2010; 20: 3043
    Google Scholar
  • 68 Chakrabarty SP, Ramapanicker R, Mishra R, Chandrasekaran S, Balaram H. Bioorg. Med. Chem.. 2009; 17: 8060
    Google Scholar
  • 69 Cornier PG, Boggián DB, Mata EG, Delpiccolo CML. Tetrahedron Lett.. 2012; 53: 632
    Google Scholar
  • 71 Guell I, Vilá S, Micalo L, Badosa E, Montesinos E, Planas M, Feliu L. Eur. J. Org. Chem.. 2013; 4933
    Google Scholar
  • 72 Vilá S, Camo C, Figueras E, Badosa E, Montesinos E, Planas M, Feliu L. Eur. J. Org. Chem.. 2014; 4785
    Google Scholar
  • 73 Wan Q, Chen J, Chen G, Danishefsky SJ. J. Org. Chem.. 2006; 71: 8244
    Google Scholar
  • 74 Kislukhin AA, Hong VP, Breitenkamp KE, Finn MG. Bioconjugate Chem.. 2013; 24: 684
    Google Scholar
  • 75 Lamandé-Langle S, Collet C, Hensienne R, Vala C, Chrétien F, Chapleur Y, Mohamadi A, Lacolley P, Regnault V. Bioorg. Med. Chem.. 2014; 22: 6672
    Google Scholar
  • 76 Soto CA, Du H.-C, Fox RG, Yang T, Hooson J, Anastasio NC, Gilbertson SR, Cunningham KA. Front. Pharmacol.. 2019; 10: 907
    Google Scholar
  • 77 Fittler H, Avrutina O, Glotzbach B, Empting M, Kolmar H. Org. Biomol. Chem.. 2013; 11: 1848
    Google Scholar
  • 78 Ferreira SZ, Carneiro HC, Lara HA, Alves RB, Resende JM, Oliveira HM, Silva LM, Santos DA, Freitas RP. ACS Med. Chem. Lett.. 2015; 6: 271
    Google Scholar
  • 79 Forner M, Defaus S, Andreu D. J. Org. Chem.. 2020; 85: 1626
    Google Scholar
  • 80 Mertens MD, Gütschow M. Synthesis. 2014; 46: 2191
    Google Scholar
  • 81 Figueras E, Martins A, Borbély A, Le Joncour V, Cordella P, Perego R, Modena D, Pagani P, Esposito S, Auciello G, Frese M, Gallinari P, Laakkonen P, Steinkühler C, Sewald N. Pharmaceutics. 2019; 11: 220
    Google Scholar
  • 82 Hofmann S, Maschauer S, Kuwert T, Beck-Sickinger AG, Prante O. Mol. Pharmacol.. 2015; 12: 1121
    Google Scholar
  • 83 Keller M, Maschauer S, Brennauer A, Tripal P, Koglin N, Dittrich R, Bernhardt G, Kuwert T, Wester H.-J, Buschauer A, Prante O. ACS Med. Chem. Lett.. 2017; 8: 304
    Google Scholar
  • 84 Borbély A, Figueras E, Martins A, Bodero L, Raposo Moreira Dias A, López Rivas P, Pina A, Arosio D, Gallinari P, Frese M, Steinkühler C, Gennari C, Piarulli U, Sewald N. ChemistryOpen. 2019; 8: 737
    Google Scholar
  • 86 Rashad AA, Song L.-R, Holmes AP, Acharya K, Zhang S, Wang Z.-L, Gary E, Xie X, Pirrone V, Kutzler MA, Long Y.-Q, Chaiken I. J. Med. Chem.. 2018; 61: 5020
    Google Scholar
  • 87 Fani M, Maecke HR, Okarvi SM. Theranostics. 2012; 2: 481
    Google Scholar
  • 88 Jackson IM, Scott PJH, Thompson S. Semin. Nucl. Med.. 2017; 47: 493
    Google Scholar
  • 89 Opalinska M, Hubalewska-Dydejczyk A, Sowa-Staszczak A. Q. J. Nucl. Med. Mol. Imaging. 2017; 61: 153
    Google Scholar
  • 90 Rangger C, Haubner R. Pharmaceuticals. 2020; 13: 38
    Google Scholar
  • 91 Morris O, Fairclough M, Grigg J, Prenant C, McMahon A. J. Labelled Compd. Radiopharm.. 2019; 62: 4
    Google Scholar
  • 92 Meyer J.-P, Adumeau P, Lewis JS, Zeglis BM. Bioconjugate Chem.. 2016; 27: 2791
    Google Scholar
  • 93 Ramenda T, Steinbach J, Wuest F. Amino Acids. 2013; 44: 1167
    Google Scholar
  • 94 Marik J, Sutcliffe JL. Tetrahedron Lett.. 2006; 47: 6681
    Google Scholar
  • 95 Iddon L, Leyton J, Indrevoll B, Glaser M, Robins EG, George AJ, Cuthbertson A, Luthra SK, Aboagye EO. Bioorg. Med. Chem. Lett.. 2011; 21: 3122
    Google Scholar
  • 96 Maschauer S, Haubner R, Kuwert T, Prante O. Mol. Pharmacol.. 2014; 11: 505
    Google Scholar
  • 97 Maschauer S, Einsiedel J, Haubner R, Hocke C, Ocker M, Hubner H, Kuwert T, Gmeiner P, Prante O. Angew. Chem. Int. Ed.. 2010; 49: 976
    Google Scholar
  • 98 Allott L, Barnes C, Brickute D, Aboagye EO. React. Chem. Eng.. 2019; 4: 569
    Google Scholar
  • 99 Dubash SR, Keat N, Mapelli P, Twyman F, Carroll L, Kozlowski K, Al-Nahhas A, Saleem A, Huiban M, Janisch R, Frilling A, Sharma R, Aboagye EO. J. Nucl. Med.. 2016; 57: 1207
    Google Scholar
  • 100 Katsamakas S, Chatzisideri T, Thysiadis S, Sarli V. Future Med. Chem.. 2017; 9: 579
    Google Scholar
  • 101 Kuijpers BHM, Groothuys S, Soede AC, Laverman P, Boerman OC, van Delft FL, Rutjes FPJT. Bioconjugate Chem.. 2007; 18: 1847
    Google Scholar
  • 102 Li Z.-B, Wu Z, Chen K, Chin FT, Chen X. Bioconjugate Chem.. 2007; 18: 1987
    Google Scholar
  • 103 Nahrwold M, Weiß C, Bogner T, Mertink F, Conradi J, Sammet B, Palmisano R, Royo Gracia S, Preuße T, Sewald N. J. Med. Chem.. 2013; 56: 1853
    Google Scholar
  • 104 Weiss C, Figueras E, Borbely AN, Sewald N. J. Pept. Sci.. 2017; 23: 514
    Google Scholar
  • 105 Borbély A, Figueras E, Martins A, Esposito S, Auciello G, Monteagudo E, Di Marco A, Summa V, Cordella P, Perego R, Kemker I, Frese M, Gallinari P, Steinkühler C, Sewald N. Pharmaceutics. 2019; 11: 151
    Google Scholar
  • 106 Essentials of Glycobiology. Varki A. Cold Spring Harbor Laboratory; Cold Spring Harbor, NY 2017
    Google Scholar
  • 107 Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X. Chem. Rev.. 2016; 116: 3086
    Google Scholar
  • 108 Lin H, Walsh CT. J. Am. Chem. Soc.. 2004; 126: 13998
    Google Scholar
  • 109 Daskhan GC, Tran HTT, Meloncelli PJ, Lowary TL, West LJ, Cairo CW. Bioconjugate Chem.. 2018; 29: 343
    Google Scholar
  • 110 Kuijpers BHM, Groothuys S, Keereweer AR, Quaedflieg PJLM, Blaauw RH, van Delft FL, Rutjes FPJT. Org. Lett.. 2004; 6: 3123
    Google Scholar
  • 111 Huang W, Groothuys S, Heredia A, Kuijpers BHM, Rutjes FPJT, van Delft FL, Wang L.-X. ChemBioChem. 2009; 10: 1234
    Google Scholar
  • 112 Groothuys S, Kuijpers BHM, Quaedflieg PJLM, Roelen HCPF, Wiertz RW, Blaauw RH, van Delft FL, Rutjes FPJT. Synthesis. 2006; 3146
    Google Scholar
  • 113 Lee DJ, Mandal K, Harris PWR, Brimble MA, Kent SBH. Org. Lett.. 2009; 11: 5270
    Google Scholar
  • 114 Lee DJ, Yang S.-H, Williams GM, Brimble MA. J. Org. Chem.. 2012; 77: 7564
    Google Scholar
  • 116 Chow HY, Zhang Y, Matheson E, Li X. Chem. Rev.. 2019; 119: 9971
    Google Scholar
  • 117 Rivera DG, Ojeda-Carralero GM, Reguera L, Van der Eycken EV. Chem. Soc. Rev.. 2020; 49: 2039
    Google Scholar
  • 120 Hacker DE, Hoinka J, Iqbal ES, Przytycka TM, Hartman MCT. ACS Chem. Biol.. 2017; 12: 795
    Google Scholar
  • 121 Springer J, de Cuba KR, Calvet-Vitale S, Geenevasen JAJ, Hermkens PHH, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem.. 2008; 2592
    Google Scholar
  • 122 Punna S, Kuzelka J, Wang Q, Finn MG. Angew. Chem. Int. Ed.. 2005; 44: 2215
    Google Scholar
  • 123 Jagasia R, Holub JM, Bollinger M, Kirshenbaum K, Finn MG. J. Org. Chem.. 2009; 74: 2964
    Google Scholar
  • 124 Angell Y, Burgess K. J. Org. Chem.. 2005; 70: 9595
    Google Scholar
  • 125 Beierle JM, Horne WS, van Maarseveen JH, Waser B, Reubi JC, Ghadiri MR. Angew. Chem. Int. Ed.. 2009; 48: 4725
    Google Scholar
  • 126 Bock VD, Speijer D, Hiemstra H, van Maarseveen JH. Org. Biomol. Chem.. 2007; 5: 971
    Google Scholar
  • 127 Horne WS, Olsen CA, Beierle JM, Montero A, Ghadiri MR. Angew. Chem. Int. Ed.. 2009; 48: 4718
    Google Scholar
  • 128 van Maarseveen JH, Horne WS, Ghadiri MR. Org. Lett.. 2005; 7: 4503
    Google Scholar
  • 129 Valverde IE, Lecaille F, Lalmanach G, Aucagne V, Delmas AF. Angew. Chem. Int. Ed.. 2012; 51: 718
    Google Scholar
  • 130 Roice M, Johannsen I, Meldal M. QSAR Comb. Sci.. 2004; 23: 662
    Google Scholar
  • 131 Cantel S, Le Chevalier-Isaad A, Scrima M, Levy JJ, DiMarchi RD, Rovero P, Halperin JA, DʼUrsi AM, Papini AM, Chorev M. J. Org. Chem.. 2008; 73: 5663
    Google Scholar
  • 132 Scrima M, Le Chevalier-Isaad A, Rovero P, Papini AM, Chorev M, DʼUrsi AM. Eur. J. Org. Chem.. 2010; 446
    Google Scholar
  • 133 Celentano V, Diana D, Di Salvo C, De Rosa L, Romanelli A, Fattorusso R, DʼAndrea LD. Chem.–Eur. J.. 2016; 22: 5534
    Google Scholar
  • 134 Diana D, Di Salvo C, Celentano V, De Rosa L, Romanelli A, Fattorusso R, DʼAndrea LD. Org. Biomol. Chem.. 2018; 16: 787
    Google Scholar
  • 136 Jacobsen , Maekawa H, Ge N.-H, Görbitz CH, Rongved P, Ottersen OP, Amiry-Moghaddam M, Klaveness J. J. Org. Chem.. 2011; 76: 1228
    Google Scholar
  • 137 Kawamoto SA, Coleska A, Ran X, Yi H, Yang C.-Y, Wang S. J. Med. Chem.. 2012; 55: 1137
    Google Scholar
  • 138 Park JH, Waters ML. Org. Biomol. Chem.. 2013; 11: 69
    Google Scholar
  • 139 Saludes JP, Morton LA, Ghosh N, Beninson LA, Chapman ER, Fleshner M, Yin H. ACS Chem. Biol.. 2012; 7: 1629
    Google Scholar
  • 140 Stefanucci A, Lei W, Pieretti S, Novellino E, Dimmito MP, Marzoli F, Streicher JM, Mollica A. Sci. Rep.. 2019; 9: 5771
    Google Scholar
  • 141 Yang J, Talibov VO, Peintner S, Rhee C, Poongavanam V, Geitmann M, Sebastiano MR, Simon B, Hennig J, Dobritzsch D, Danielson UH, Kihlberg J. ACS Omega. 2020; 5: 3979
    Google Scholar
  • 142 Lau YH, de Andrade P, McKenzie GJ, Venkitaraman AR, Spring DR. ChemBioChem. 2014; 15: 2680
    Google Scholar
  • 143 Lau YH, de Andrade P, Quah S.-T, Rossmann M, Laraia L, Sköld N, Sum TJ, Rowling PJE, Joseph TL, Verma C, Hyvönen M, Itzhaki LS, Venkitaraman AR, Brown CJ, Lane DP, Spring DR. Chem. Sci.. 2014; 5: 1804
    Google Scholar
  • 144 Turner RA, Oliver AG, Lokey RS. Org. Lett.. 2007; 9: 5011
    Google Scholar
  • 145 Reddy NC, Kumar M, Molla R, Rai V. Org. Biomol. Chem.. 2020; 18: 4669
    Google Scholar
  • 146 Ravasco JMJM, Faustino H, Trindade A, Gois PMP. Chem.–Eur. J.. 2019; 25: 43
    Google Scholar
  • 149 Voloshchuk N, Montclare JK. Mol. Biosyst.. 2010; 6: 65
    Google Scholar
  • 150 Johnson JA, Lu YY, Van Deventer JA, Tirrell DA. Curr. Opin. Chem. Biol.. 2010; 14: 774
    Google Scholar
  • 151 tom Dieck S, Müller A, Nehring A, Hinz FI, Bartnik I, Schuman EM, Dieterich DC. Curr. Protoc. Cell Biol.. 2012; 56: 7.11.1
    Google Scholar
  • 152 Dieterich DC, Link AJ, Graumann J, Tirrell DA, Schuman EM. Proc. Natl. Acad. Sci. U. S. A.. 2006; 103: 9482
    Google Scholar
  • 153 Dieterich DC, Hodas JJL, Gouzer G, Shadrin IY, Ngo JT, Triller A, Tirrell DA, Schuman EM. Nat. Neurosci.. 2010; 13: 897
    Google Scholar
  • 154 Liu CC, Schultz PG. Annu. Rev. Biochem.. 2010; 79: 413
    Google Scholar
  • 155 Davis L, Chin JW. Nat. Rev. Mol. Cell Biol.. 2012; 13: 168
    Google Scholar
  • 156 Xie J, Schultz PG. Nat. Rev. Mol. Cell Biol.. 2006; 7: 775
    Google Scholar
  • 157 Smolskaya S, Andreev YA. Biomolecules. 2019; 9: 255
    Google Scholar
  • 158 Wang L, Brock A, Herberich B, Schultz PG. Science (Washington, D. C.). 2001; 292: 498
    Google Scholar
  • 159 Xiao H, Schultz PG. Cold Spring Harbor Perspect. Biol.. 2016; 8: a023 945
    Google Scholar
  • 160 Beatty KE, Liu JC, Xie F, Dieterich DC, Schuman EM, Wang Q, Tirrell DA. Angew. Chem. Int. Ed.. 2006; 45: 7364
    Google Scholar
  • 161 Beatty KE, Xie F, Wang Q, Tirrell DA. J. Am. Chem. Soc.. 2005; 127: 14150
    Google Scholar
  • 162 Beatty KE, Tirrell DA. Bioorg. Med. Chem. Lett.. 2008; 18: 5995
    Google Scholar
  • 163 Tcherkezian J, Brittis PA, Thomas F, Roux PP, Flanagan JG. Cell. 2010; 141: 632
    Google Scholar
  • 164 Zhang MM, Tsou LK, Charron G, Raghavan AS, Hang HC. Proc. Natl. Acad. Sci. U. S. A.. 2010; 107: 8627
    Google Scholar
  • 165 Calve S, Witten AJ, Ocken AR, Kinzer-Ursem TL. Sci. Rep.. 2016; 6: 32377
    Google Scholar
  • 166 Saleh AM, Jacobson KR, Kinzer-Ursem TL, Calve S. Cell. Mol. Bioeng.. 2019; 12: 495
    Google Scholar
  • 167 Link AJ, Vink MKS, Agard NJ, Prescher JA, Bertozzi CR, Tirrell DA. Proc. Natl. Acad. Sci. U. S. A.. 2006; 103: 10180
    Google Scholar
  • 168 Ngo JT, Champion JA, Mahdavi A, Tanrikulu IC, Beatty KE, Connor RE, Yoo TH, Dieterich DC, Schuman EM, Tirrell DA. Nat. Chem. Biol.. 2009; 5: 715
    Google Scholar
  • 169 Abdeljabbar DM, Klein TJ, Zhang S, Link AJ. J. Am. Chem. Soc.. 2009; 131: 17078
    Google Scholar
  • 170 Kirshenbaum K, Carrico IS, Tirrell DA. ChemBioChem. 2002; 3: 235
    Google Scholar
  • 171 Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q. Org. Lett.. 2004; 6: 4603
    Google Scholar
  • 173 Dean KM, Palmer AE. Nat. Chem. Biol.. 2014; 10: 512
    Google Scholar
  • 175 Lin VS, Lippert AR, Chang CJ. Methods Enzymol.. 2015; 554: 63
    Google Scholar
  • 176 Speers AE, Cravatt BF. Chem. Biol.. 2004; 11: 535
    Google Scholar
  • 177 Worrell BT, Malik JA, Fokin VV. Science (Washington, D. C.). 2013; 340: 457
    Google Scholar
  • 179 Nadler A, Schultz C. Angew. Chem. Int. Ed.. 2013; 52: 2408
    Google Scholar
  • 180 Kozma E, Kele P. Org. Biomol. Chem.. 2019; 17: 215
    Google Scholar
  • 181 Deiters A, Cropp TA, Mukherji M, Chin JW, Anderson JC, Schultz PG. J. Am. Chem. Soc.. 2003; 125: 11782
    Google Scholar
  • 182 Wan W, Huang Y, Wang Z, Russell WK, Pai P.-J, Russell DH, Liu WR. Angew. Chem. Int. Ed.. 2010; 49: 3211
    Google Scholar
  • 183 Kele P, Mezo G, Achatz D, Wolfbeis OS. Angew. Chem. Int. Ed.. 2009; 48: 344
    Google Scholar
  • 184 Lin S, Zhang Z, Xu H, Li L, Chen S, Li J, Hao Z, Chen PR. J. Am. Chem. Soc.. 2011; 133: 20581
    Google Scholar
  • 185 Lim SI, Mizuta Y, Takasu A, Kim YH, Kwon I. PLoS One. 2014; 9: e98 403
    Google Scholar
  • 186 Hao Z, Song Y, Lin S, Yang M, Liang Y, Wang J, Chen PR. Chem. Commun. (Cambridge). 2011; 47: 4502
    Google Scholar
  • 188 Jiang H, Zheng T, Lopez-Aguilar A, Feng L, Kopp F, Marlow FL, Wu P. Bioconjugate Chem.. 2014; 25: 698
    Google Scholar
  • 189 Uttamapinant C, Tangpeerachaikul A, Grecian S, Clarke S, Singh U, Slade P, Gee KR, Ting AY. Angew. Chem. Int. Ed.. 2012; 51: 5852
    Google Scholar
  • 190 Bevilacqua V, King M, Chaumontet M, Nothisen M, Gabillet S, Buisson D, Puente C, Wagner A, Taran F. Angew. Chem. Int. Ed.. 2014; 53: 5872
    Google Scholar
  • 191 Li S, Wang L, Yu F, Zhu Z, Shobaki D, Chen H, Wang M, Wang J, Qin G, Erasquin UJ, Ren L, Wang Y, Cai C. Chem. Sci.. 2017; 8: 2107
    Google Scholar
  • 192 Erdmann I, Marter K, Kobler O, Niehues S, Abele J, Müller A, Bussmann J, Storkebaum E, Ziv T, Thomas U, Dieterich DC. Nat. Commun.. 2015; 6: 7521
    Google Scholar
  • 193 Hinz FI, Dieterich DC, Tirrell DA, Schuman EM. ACS Chem. Neurosci.. 2012; 3: 40
    Google Scholar
  • 194 Kos A, Wanke KA, Gioio A, Martens GJ, Kaplan BB, Aschrafi A. J. Histochem. Cytochem.. 2016; 64: 323
    Google Scholar
  • 195 Teunissen AJP, Pérez-Medina C, Meijerink A, Mulder WJM. Chem. Soc. Rev.. 2018; 47: 7027
    Google Scholar
  • 196 Lin W, Du Y, Zhu Y, Chen X. J. Am. Chem. Soc.. 2014; 136: 679
    Google Scholar
  • 197 Yang Y, Lin S, Lin W, Chen PR. ChemBioChem. 2014; 15: 1738
    Google Scholar
  • 198 Fekner T, Li X, Lee MM, Chan MK. Angew. Chem. Int. Ed.. 2009; 48: 1633
    Google Scholar
  • 199 Sasmal DK, Pulido LE, Kasal S, Huang J. Nanoscale. 2016; 8: 19928
    Google Scholar
  • 200 Milles S, Tyagi S, Banterle N, Koehler C, VanDelinder V, Plass T, Neal AP, Lemke EA. J. Am. Chem. Soc.. 2012; 134: 5187
    Google Scholar
  • 201 Hamadani KM, Howe J, Jensen MK, Wu P, Cate JHD, Marqusee S. J. Biol. Chem.. 2017; 292: 15636
    Google Scholar
  • 202 Moremen KW, Tiemeyer M, Nairn AV. Nat. Rev. Mol. Cell Biol.. 2012; 13: 448
    Google Scholar
  • 203 van Kasteren SI, Kramer HB, Jensen HH, Campbell SJ, Kirkpatrick J, Oldham NJ, Anthony DC, Davis BG. Nature (London). 2007; 446: 1105
    Google Scholar
  • 204 van Kasteren SI, Kramer HB, Gamblin DP, Davis BG. Nat. Protoc.. 2007; 2: 3185
    Google Scholar
  • 205 Kaya E, Gutsmiedl K, Vrabel M, Müller M, Thumbs P, Carell T. ChemBioChem. 2009; 10: 2858
    Google Scholar
  • 206 Lee DJ, Cameron AJ, Wright TH, Harris PWR, Brimble MA. Chem. Sci.. 2019; 10: 815
    Google Scholar
  • 207 Machida T, Winssinger N. ChemBioChem. 2016; 17: 811
    Google Scholar
  • 208 Glaser M, Robins EG. J. Labelled Compd. Radiopharm.. 2009; 52: 407
    Google Scholar
  • 209 Wangler C, Schirrmacher R, Bartenstein P, Wangler B. Curr. Med. Chem.. 2010; 17: 1092
    Google Scholar
  • 210 Chang YS, Jeong JM, Lee Y.-S, Kim HW, Rai GB, Lee SJ, Lee DS, Chung J.-K, Lee MC. Bioconjugate Chem.. 2005; 16: 1329
    Google Scholar
  • 211 Wester H.-J, Hamacher K, Stöcklin G. Nucl. Med. Biol.. 1996; 23: 365
    Google Scholar
  • 212 Boutureira O, DʼHooge F, Fernández-González M, Bernardes GJL, Sánchez-Navarro M, Koeppe JR, Davis BG. Chem. Commun. (Cambridge). 2010; 46: 8142
    Google Scholar
  • 214 Roser P, Schmidt MJ, Drescher M, Summerer D. Org. Biomol. Chem.. 2016; 14: 5468
    Google Scholar
  • 215 Kucher S, Korneev S, Tyagi S, Apfelbaum R, Grohmann D, Lemke EA, Klare JP, Steinhoff H.-J, Klose D. J. Magn. Reson.. 2017; 275: 38
    Google Scholar
  • 216 Widder P, Berner F, Summerer D, Drescher M. ACS Chem. Biol.. 2019; 14: 839
    Google Scholar
  • 217 Widder P, Schuck J, Summerer D, Drescher M. Phys. Chem. Chem. Phys.. 2020; 22: 4875
    Google Scholar
  • 218 Abdelkader EH, Feintuch A, Yao X, Adams LA, Aurelio L, Graham B, Goldfarb D, Otting G. Chem. Commun. (Cambridge). 2015; 51: 15898
    Google Scholar
  • 219 Khongorzul P, Ling CJ, Khan FU, Ihsan AU, Zhang J. Mol. Cancer Res.. 2020; 18: 3
    Google Scholar
  • 220 Chari RV, Miller ML, Widdison WC. Angew. Chem. Int. Ed.. 2014; 53: 3796
    Google Scholar
  • 221 Akkapeddi P, Azizi S.-A, Freedy AM, Cal PMSD, Gois PMP, Bernardes GJL. Chem. Sci.. 2016; 7: 2954
    Google Scholar
  • 222 Zhao P, Zhang Y, Li W, Jeanty C, Xiang G, Dong Y. Acta Pharm. Sin. B. 2020; 10: 1589
    Google Scholar
  • 223 Lambert JM, Berkenblit A. Annu. Rev. Med.. 2018; 69: 191
    Google Scholar
  • 224 Smith MEB, Schumacher FF, Ryan CP, Tedaldi LM, Papaioannou D, Waksman G, Caddick S, Baker JR. J. Am. Chem. Soc.. 2010; 132: 1960
    Google Scholar
  • 225 Bryden F, Maruani A, Savoie H, Chudasama V, Smith MEB, Caddick S, Boyle RW. Bioconjugate Chem.. 2014; 25: 611
    Google Scholar
  • 226 VanBrunt MP, Shanebeck K, Caldwell Z, Johnson J, Thompson P, Martin T, Dong H, Li G, Xu H, DʼHooge F, Masterson L, Bariola P, Tiberghien A, Ezeadi E, Williams DG, Hartley JA, Howard PW, Grabstein KH, Bowen MA, Marelli M. Bioconjugate Chem.. 2015; 26: 2249
    Google Scholar
  • 227 Swiderska KW, Szlachcic A, Czyrek A, Zakrzewska M, Otlewski J. Bioorg. Med. Chem.. 2017; 25: 3685
    Google Scholar
  • 228 Harris JM, Chess RB. Nat. Rev. Drug Discovery. 2003; 2: 214
    Google Scholar
  • 229 Roberts MJ, Bentley MD, Harris JM. Adv. Drug Delivery Rev.. 2002; 54: 459
    Google Scholar
  • 230 Turecek PL, Bossard MJ, Schoetens F, Ivens IA. J. Pharm. Sci.. 2016; 105: 460
    Google Scholar
  • 231 Belén LH, Rangel-Yagui CdO, Beltrán Lissabet JF, Effer B, Lee-Estevez M, Pessoa A, Castillo RL, Farías JG. Front. Pharmacol.. 2019; 10: 1450
    Google Scholar
  • 232 Deiters A, Cropp TA, Summerer D, Mukherji M, Schultz PG. Bioorg. Med. Chem. Lett.. 2004; 14: 5743
    Google Scholar
  • 233 Nairn NW, Shanebeck KD, Wang A, Graddis TJ, VanBrunt MP, Thornton KC, Grabstein K. Bioconjugate Chem.. 2012; 23: 2087
    Google Scholar
  • 235 Niemeyer CM. Angew. Chem. Int. Ed.. 2010; 49: 1200
    Google Scholar
  • 236 Sano T, Smith CL, Cantor CR. Science (Washington, D. C.). 1992; 258: 120
    Google Scholar
  • 237 Khatwani SL, Kang JS, Mullen DG, Hast MA, Beese LS, Distefano MD, Taton TA. Bioorg. Med. Chem.. 2012; 20: 4532
    Google Scholar
  • 238 Synakewicz M, Bauer D, Rief M, Itzhaki LS. Sci. Rep.. 2019; 9: 13820
    Google Scholar
  • 239 Witte MD, Cragnolini JJ, Dougan SK, Yoder NC, Popp MW, Ploegh HL. Proc. Natl. Acad. Sci. U. S. A.. 2012; 109: 11993
    Google Scholar
  • 240 Baalmann M, Neises L, Bitsch S, Schneider H, Deweid L, Werther P, Ilkenhans N, Wolfring M, Ziegler MJ, Wilhelm J, Kolmar H, Wombacher R. Angew. Chem. Int. Ed.. 2020; 59: 12885
    Google Scholar
  • 242 Foot JS, Lui FE, Kluger R. Chem. Commun. (Cambridge). 2009; 7315
    Google Scholar
  • 243 Bundy BC, Swartz JR. Bioconjugate Chem.. 2010; 21: 255
    Google Scholar
  • 245 Eger S, Scheffner M, Marx A, Rubini M. J. Am. Chem. Soc.. 2010; 132: 16337
    Google Scholar
  • 246 Eger S, Castrec B, Hübscher U, Scheffner M, Rubini M, Marx A. ChemBioChem. 2011; 12: 2807
    Google Scholar
  • 247 Schneider D, Schneider T, Rösner D, Scheffner M, Marx A. Bioorg. Med. Chem.. 2013; 21: 3430
    Google Scholar
  • 248 Schneider T, Schneider D, Rösner D, Malhotra S, Mortensen F, Mayer TU, Scheffner M, Marx A. Angew. Chem. Int. Ed.. 2014; 53: 12925
    Google Scholar
  • 250 Sommer S, Weikart ND, Brockmeyer A, Janning P, Mootz HD. Angew. Chem. Int. Ed.. 2011; 50: 9888
    Google Scholar
  • 251 Rösner D, Schneider T, Schneider D, Scheffner M, Marx A. Nat. Protoc.. 2015; 10: 1594
    Google Scholar