Advances in Merging Triazoles with Peptides and Proteins

Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 48)

Abstract

Five-membered heterocycles have found extensive use as peptide- and disulfide-bond mimics in peptidomimetics. The application of 1,4- and 1,5-substituted 1,2,3-triazoles has been particularly favored due to their ease of preparation by a variety of “click” methods including the copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and the ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) reactions. These heterocycles are electronically similar to amide bonds and have provided both functional and structural analogues of biologically active peptides. One advantage of triazole ring amide surrogates is their stability toward natural enzyme activity. The quantitative and orthogonal nature of the CuAAC reaction has facilitated its use in peptide macrocyclization reactions. The CuAAC reaction is particularly useful to replace disulfide bonds in order to stabilize bioactive conformations of biologically active peptides. Metal-free cycloadditions promoted by ring strain (SPAAC) have been favored for labeling in living systems in which transition metals are poorly tolerated. A range of in vivo biomolecular “click” reactions have demonstrated the versatility of SPAAC reactions in living cells and even multicellular organisms. Although azides and alkynes can conveniently be introduced in peptides during synthesis, site-specific incorporation of these functional groups into proteins is more challenging. A variety of methods has been developed to make these reactive precursors, including residue-specific replacement and genetic code expansion. Recent developments of new ligands and catalysts for the CuAAC reaction have further contributed to the promising possibilities that triazoles provide for future applications in the peptide and protein field.

Keywords

Click reaction CuAAC Macrocyclization Peptide mimetics Protein labeling RuAAC SPAAC Triazole 

References

  1. 1.
    Yan WY, Zhou JH, Sun MM, Chen JJ, Hu G, Shen BR (2014) Amino Acids 46:1419CrossRefGoogle Scholar
  2. 2.
    Fletcher MD, Campbell MM (1998) Chem Rev 98:763CrossRefGoogle Scholar
  3. 3.
    Moulin A, Bibian M, Blayo AL, El Habnouni S, Martinez J, Fehrentz JA (2010) Chem Rev 110:1809CrossRefGoogle Scholar
  4. 4.
    Borg S, Estenne-Bouhtou G, Luthman K, Csoeregh I, Hesselink W, Hacksell U (1995) J Org Chem 60:3112CrossRefGoogle Scholar
  5. 5.
    Tornøe CW, Meldal M (2001) Peptidotriazoles: copper(I)-catalyzed 1,3-dipolar cycloadditions on solid-phase. In: Lebl M, Houghten RA (eds) Peptides 2001, Proc. Am. Pept. Symp. Kluwer, San Diego, p 263Google Scholar
  6. 6.
    Agard NJ, Prescher JA, Bertozzi CR (2004) J Am Chem Soc 126:15046CrossRefGoogle Scholar
  7. 7.
    Angell YL, Burgess K (2007) Chem Soc Rev 36:1674CrossRefGoogle Scholar
  8. 8.
    Meldal M, Tornøe CW (2008) Chem Rev 108:2952CrossRefGoogle Scholar
  9. 9.
    Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA (2008) Med Res Rev 28:278CrossRefGoogle Scholar
  10. 10.
    Tornøe CW, Meldal M (2009) Dipolar cycloaddition reactions in peptide chemistry. In: Bräse S, Banert K (eds) Organic azides: syntheses and applications. Wiley, Chichester, p 285, Chapter 10CrossRefGoogle Scholar
  11. 11.
    Holub JM, Kirshenbaum K (2010) Chem Soc Rev 39:1325CrossRefGoogle Scholar
  12. 12.
    Pedersen DS, Abell A (2011) Eur J Org Chem 2011:2399CrossRefGoogle Scholar
  13. 13.
    Li X (2011) Chem Asian J 6:2606CrossRefGoogle Scholar
  14. 14.
    Pasini D (2013) Molecules 18:9512CrossRefGoogle Scholar
  15. 15.
    Ahmad Fuaad AA, Azmi F, Skwarczynski M, Toth I (2013) Molecules 18:13148CrossRefGoogle Scholar
  16. 16.
    Valverde IE, Mindt TL (2013) CHIMIA Int J Chem 67:262CrossRefGoogle Scholar
  17. 17.
    De Lombaert S, Stamford LB, Blanchard L, Tan J, Hoyer D, Diefenbacher CG, Wei D, Wallace EM, Moskal MA, Savage P, Jeng AY (1997) Bioorg Med Chem Lett 7:1059CrossRefGoogle Scholar
  18. 18.
    Cesar J, Sollner M (2000) Synth Commun 30:4147CrossRefGoogle Scholar
  19. 19.
    Hitotsuyanagi Y, Motegi S, Fukaya H, Takeya K (2002) J Org Chem 67:3266CrossRefGoogle Scholar
  20. 20.
    Hitotsuyanagi Y, Motegi S, Hasuda T, Takeya K (2004) Org Lett 6:1111CrossRefGoogle Scholar
  21. 21.
    Boeglin D, Cantel S, Heitz A, Martinez J, Fehrentz JA (2003) Org Lett 5:4465CrossRefGoogle Scholar
  22. 22.
    Bibian M, Blayo AL, Moulin A, Martinez J, Fehrentz JA (2010) Tetrahedron Lett 51:2660CrossRefGoogle Scholar
  23. 23.
    Blayo A-L, Brunel F, Martinez J, Fehrentz J-A (2011) Eur J Org Chem 2011:4293CrossRefGoogle Scholar
  24. 24.
    Schulze B, Schubert US (2014) Chem Soc Rev 43:2522CrossRefGoogle Scholar
  25. 25.
    Ramasastry SS (2014) Angew Chem Int Ed 53:14310CrossRefGoogle Scholar
  26. 26.
    Buckley BR, Heaney H (2012) Mechanistic investigations of copper (I)-catalysed alkyne-azide cycloaddition reactions. In: Košmrlj J (ed) Click triazoles. Springer, Berlin, p 1Google Scholar
  27. 27.
    Bock VD, Hiemstra H, Van Maarseveen JH (2006) Eur J Org Chem 51Google Scholar
  28. 28.
    Schoffelen S, Meldal M (2014) Alkyne-azide cycloadditions. In: Li CJ, Trost BM (eds) Modern alkyne chemistry: catalytic and atom-economic transformations. Wiley, WeinheimGoogle Scholar
  29. 29.
    Wu P, Fokin VV (2007) Aldrichchim Acta 40:7Google Scholar
  30. 30.
    Huisgen R (1963) Angew Chem Int Ed Engl 2:565CrossRefGoogle Scholar
  31. 31.
    Huisgen R, Szeimies G, Moebius L (1967) Chem Ber 100:2494CrossRefGoogle Scholar
  32. 32.
    Pokorski JK, Miller Jenkins LM, Feng H, Durell SR, Bai Y, Appella DH (2007) Org Lett 9:2381CrossRefGoogle Scholar
  33. 33.
    Horne WS, Olsen CA, Beierle JM, Montero A, Ghadiri MR (2009) Angew Chem Int Ed 48:4718CrossRefGoogle Scholar
  34. 34.
    Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057CrossRefGoogle Scholar
  35. 35.
    Bock VD, Perciaccante R, Jansen TP, Hiemstra H, Van Maarseveen JH (2006) Org Lett 8:919CrossRefGoogle Scholar
  36. 36.
    Shao C, Cheng G, Su D, Xu J, Wang X, Hu Y (2010) Adv Synth Catal 352:1587CrossRefGoogle Scholar
  37. 37.
    Berg R, Straub J, Schreiner E, Mader S, Rominger F, Straub BF (2012) Adv Synth Catal 354:3445CrossRefGoogle Scholar
  38. 38.
    Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596CrossRefGoogle Scholar
  39. 39.
    Oh K, Guan Z (2006) Chem Commun 3069Google Scholar
  40. 40.
    Worrell BT, Malik JA, Fokin VV (2013) Science 340:457CrossRefGoogle Scholar
  41. 41.
    Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) J Am Chem Soc 125:3192CrossRefGoogle Scholar
  42. 42.
    Chan TR, Hilgraf R, Sharpless KB, Fokin VV (2004) Org Lett 6:2853CrossRefGoogle Scholar
  43. 43.
    Hong V, Presolski SI, Ma C, Finn MG (2009) Angew Chem Int Ed 48:9879CrossRefGoogle Scholar
  44. 44.
    Rodionov VO, Presolski SI, Diaz DD, Fokin VV, Finn MG (2007) J Am Chem Soc 129:12705CrossRefGoogle Scholar
  45. 45.
    Michaels HA, Zhu L (2011) Chem Asian J 6:2825CrossRefGoogle Scholar
  46. 46.
    Chouhan G, James K (2011) Org Lett 13:2754CrossRefGoogle Scholar
  47. 47.
    Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998CrossRefGoogle Scholar
  48. 48.
    Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV (2008) J Am Chem Soc 130:8923CrossRefGoogle Scholar
  49. 49.
    Boz E, Tüzün NS (2013) J Organomet Chem 724:167CrossRefGoogle Scholar
  50. 50.
    Majireck MM, Weinreb SM (2006) J Org Chem 71:8680CrossRefGoogle Scholar
  51. 51.
    Kelly AR, Wei J, Kesavan S, Marié JC, Windmon N, Young DW, Marcaurelle LA (2009) Org Lett 11:2257CrossRefGoogle Scholar
  52. 52.
    Zhang JQ, Kemmink J, Rijkers DTS, Liskamp RMJ (2013) Chem Commun 49:4498CrossRefGoogle Scholar
  53. 53.
    Blomquist AT, Liu LH (1953) J Am Chem Soc 75:2153CrossRefGoogle Scholar
  54. 54.
    Wittig G, Krebs A (1961) Chem Ber 94:3260CrossRefGoogle Scholar
  55. 55.
    Jewett JC, Bertozzi CR (2010) Chem Soc Rev 39:1272CrossRefGoogle Scholar
  56. 56.
    Ahsanullah, Schmieder P, Kühne R, Rademann J (2009) Angew Chem Int Ed 48:5042CrossRefGoogle Scholar
  57. 57.
    Ahsanullah, Rademann J (2010) Angew Chem Int Ed 49:5378CrossRefGoogle Scholar
  58. 58.
    Niu T, Gu L, Wang L, Yi W, Cai C (2012) Eur J Org Chem 2012:6767CrossRefGoogle Scholar
  59. 59.
    Angelo NG, Arora PS (2005) J Am Chem Soc 127:17134CrossRefGoogle Scholar
  60. 60.
    Zhang Z, Fan E (2006) Tetrahedron Lett 47:665CrossRefGoogle Scholar
  61. 61.
    Angelo NG, Arora PS (2007) J Org Chem 72:7964CrossRefGoogle Scholar
  62. 62.
    Jochim AL, Miller SE, Angelo NG, Arora PS (2009) Bioorg Med Chem Lett 19:6023CrossRefGoogle Scholar
  63. 63.
    Aucagne V, Leigh DA (2006) Org Lett 8:4505CrossRefGoogle Scholar
  64. 64.
    Montagnat OD, Lessene G, Hughes AB (2010) J Org Chem 75:390CrossRefGoogle Scholar
  65. 65.
    Johansson JR, Hermansson E, Nordén B, Kann N, Beke-Somfai T (2014) Eur J Org Chem 2014:2703CrossRefGoogle Scholar
  66. 66.
    Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128CrossRefGoogle Scholar
  67. 67.
    Ko E, Liu J, Perez LM, Lu G, Schaefer A, Burgess K (2011) J Am Chem Soc 133:462CrossRefGoogle Scholar
  68. 68.
    Ko E, Liu J, Burgess K (2011) Chem Soc Rev 40:4411CrossRefGoogle Scholar
  69. 69.
    Abboud J-LM, Foces-Foces C, Notario R, Trifonov RE, Volovodenko AP, Ostrovskii VA, Alkorta I, Elguero J (2001) Eur J Org Chem 2001:3013CrossRefGoogle Scholar
  70. 70.
    Garnovskii AD, Kolodyazhnyi YV, Osipov OA, Minkin VI, Giller SA, Mazheika IB, Grandberg II (1971) Chem Heterocycl Compd 7:809CrossRefGoogle Scholar
  71. 71.
    Massarotti A, Aprile S, Mercalli V, Del Grosso E, Grosa G, Sorba G, Tron GC (2014) ChemMedChem 9:2497CrossRefGoogle Scholar
  72. 72.
    Horne WS, Yadav MK, Stout CD, Ghadiri MR (2004) J Am Chem Soc 126:15366CrossRefGoogle Scholar
  73. 73.
    Tornøe CW, Sanderson SJ, Mottram JC, Coombs GH, Meldal M (2004) J Comb Chem 6:312CrossRefGoogle Scholar
  74. 74.
    St Hilaire PM, Alves LC, Sanderson SJ, Mottram JC, Juliano MA, Juliano L, Coombs GH, Meldal M (2000) ChemBioChem 1:115CrossRefGoogle Scholar
  75. 75.
    Güell I, Micaló L, Cano L, Badosa E, Ferre R, Montesinos E, Bardají E, Feliu L, Planas M (2012) Peptides 33:9CrossRefGoogle Scholar
  76. 76.
    Tam A, Arnold U, Soellner MB, Raines RT (2007) J Am Chem Soc 129:12670CrossRefGoogle Scholar
  77. 77.
    Roice M, Johannsen I, Meldal M (2004) QSAR Comb Sci 23:662CrossRefGoogle Scholar
  78. 78.
    Turner RA, Oliver AG, Lokey RS (2007) Org Lett 9:5011CrossRefGoogle Scholar
  79. 79.
    Jagasia R, Holub JM, Bollinger M, Kirshenbaum K, Finn MG (2009) J Org Chem 74:2964CrossRefGoogle Scholar
  80. 80.
    Angell Y, Burgess K (2005) J Org Chem 70:9595CrossRefGoogle Scholar
  81. 81.
    Meutermans WD, Bourne GT, Golding SW, Horton DA, Campitelli MR, Craik D, Scanlon M, Smythe ML (2003) Org Lett 5:2711CrossRefGoogle Scholar
  82. 82.
    Schmidt U, Langner J (1997) J Pept Res 49:67CrossRefGoogle Scholar
  83. 83.
    Hill TA, Shepherd NE, Diness F, Fairlie DP (2014) Angew Chem Int Ed 53:13020CrossRefGoogle Scholar
  84. 84.
    Kawamoto SA, Coleska A, Ran X, Yi H, Yang CY, Wang S (2012) J Med Chem 55:1137CrossRefGoogle Scholar
  85. 85.
    de Araujo AD, Hoang HN, Kok WM, Diness F, Gupta P, Hill TA, Driver RW, Price DA, Liras S, Fairlie DP (2014) Angew Chem Int Ed 53:6965CrossRefGoogle Scholar
  86. 86.
    Ingale S, Dawson PE (2011) Org Lett 13:2822CrossRefGoogle Scholar
  87. 87.
    Jacobsen Ø, Maekawa H, Ge NH, Gőrbitz CH, Rongved P, Ottersen OP, Amiry-Moghaddam M, Klaveness J (2011) J Org Chem 76:1228CrossRefGoogle Scholar
  88. 88.
    Pehere AD, Abell AD (2012) Org Lett 14:1330CrossRefGoogle Scholar
  89. 89.
    Pehere AD, Sumby CJ, Abell AD (2013) Org Biomol Chem 11:425CrossRefGoogle Scholar
  90. 90.
    Celentano V, Diana D, De Rosa L, Romanelli A, Fattorusso R, D’Andrea LD (2012) Chem Commun 48:762CrossRefGoogle Scholar
  91. 91.
    Park JH, Waters ML (2013) Org Biomol Chem 11:69CrossRefGoogle Scholar
  92. 92.
    Empting M, Avrutina O, Meusinger R, Fabritz S, Reinwarth M, Biesalski M, Voigt S, Buntkowsky G, Kolmar H (2011) Angew Chem Int Ed 50:5207CrossRefGoogle Scholar
  93. 93.
    Holland-Nell K, Meldal M (2011) Angew Chem Int Ed 123:5310CrossRefGoogle Scholar
  94. 94.
    Kee JM, Villani B, Carpenter LR, Muir TW (2010) J Am Chem Soc 132:14327CrossRefGoogle Scholar
  95. 95.
    McAllister TE, Webb ME (2012) Org Biomol Chem 10:4043CrossRefGoogle Scholar
  96. 96.
    Mukai S, Flematti GR, Byrne LT, Besant PG, Attwood PV, Piggott MJ (2012) Amino Acids 43:857CrossRefGoogle Scholar
  97. 97.
    Buysse K, Farard J, Nikolaou A, Vanderheyden P, Vauquelin G, Sejer Pedersen D, Tourwé D, Ballet S (2011) Org Lett 13:6468CrossRefGoogle Scholar
  98. 98.
    Van der Poorten O, Fehér K, Buysse K, Feytens D, Zoi I, Schwartz SD, Martins JC, Tourwé D, Cai M, Hruby VJ, Ballet S (2014) ACS Med Chem Lett 6:192CrossRefGoogle Scholar
  99. 99.
    van der Knaap M, Lageveen LT, Busscher HJ, Mars-Groenendijk R, Noort D, Otero JM, Llamas-Saiz AL, van Raaij MJ, van der Marel GA, Overkleeft HS, Overhand M (2011) ChemMedChem 6:840CrossRefGoogle Scholar
  100. 100.
    Fittler H, Avrutina O, Glotzbach B, Empting M, Kolmar H (2013) Org Biomol Chem 11:1848CrossRefGoogle Scholar
  101. 101.
    Qiu HB, Chen XY, Li Q, Qian WJ, Yu SM, Tang GL, Yao ZJ (2014) Tetrahedron Lett 55:6055CrossRefGoogle Scholar
  102. 102.
    Kuijpers BHM, Groothuys S, Keereweer AR, Quaedflieg PJLM, Blaauw RH, Van Delft FL, Rutjes FPJT (2004) Org Lett 6:3123CrossRefGoogle Scholar
  103. 103.
    Kuijpers BH, Groothuys S, Hawner C, Dam J, Quaedflieg PJ, Schoemaker HE, Delft FL, Rutjes FP (2008) Org Process Res Dev 12:503CrossRefGoogle Scholar
  104. 104.
    Huang W, Groothuys S, Heredia A, Kuijpers BH, Rutjes FP, van Delft FL, Wang L-X (2009) ChemBioChem 10:1234CrossRefGoogle Scholar
  105. 105.
    Miller N, Williams GM, Brimble MA (2009) Org Lett 11:2409CrossRefGoogle Scholar
  106. 106.
    Capicciotti CJ, Trant JF, Leclere M, Ben RN (2011) Bioconjug Chem 22:605CrossRefGoogle Scholar
  107. 107.
    Kowalczyk R, Brimble MA, Tomabechi Y, Fairbanks AJ, Fletcher M, Hay DL (2014) Org Biomol Chem 12:8142CrossRefGoogle Scholar
  108. 108.
    Boutureira O, D’Hooge F, Fernández-González M, Bernardes GJ, Sánchez-Navarro M, Koeppe JR, Davis BG (2010) Chem Commun 46:8142CrossRefGoogle Scholar
  109. 109.
    Maschauer S, Haubner R, Kuwert T, Prante O (2013) Mol Pharm 11:505CrossRefGoogle Scholar
  110. 110.
    Lang K, Chin JW (2014) Chem Rev 114:4764CrossRefGoogle Scholar
  111. 111.
    Ngo JT, Tirrell DA (2011) Acc Chem Res 44:677CrossRefGoogle Scholar
  112. 112.
    Johnson JA, Lu YY, Van Deventer JA, Tirrell DA (2010) Curr Opin Chem Biol 14:774CrossRefGoogle Scholar
  113. 113.
    Davis L, Chin JW (2012) Nat Rev Mol Cell Biol 13:168Google Scholar
  114. 114.
    Liu CC, Schultz PG (2010) Ann Rev Biochem 79:413CrossRefGoogle Scholar
  115. 115.
    Matsumoto T, Tanaka T, Kondo A (2012) Biotechnol J 7:1137CrossRefGoogle Scholar
  116. 116.
    van Geel R, Debets MF, Lowik DWPM, Pruijn GJM, Boelens WC (2012) Amino Acids 43:1251CrossRefGoogle Scholar
  117. 117.
    Fernandez-Suarez M, Baruah H, Martinez-Hernandez L, Xie KT, Baskin JM, Bertozzi CR, Ting AY (2007) Nat Biotechnol 25:1483CrossRefGoogle Scholar
  118. 118.
    Witte MD, Cragnolini JJ, Dougan SK, Yoder NC, Popp MW, Ploegh HL (2012) Proc Natl Acad Sci U S A 109:11993CrossRefGoogle Scholar
  119. 119.
    Lin PC, Ueng SH, Tseng MC, Ko JL, Huang KT, Yu SC, Adak AK, Chen YJ, Lin CC (2006) Angew Chem Int Ed 45:4286CrossRefGoogle Scholar
  120. 120.
    Kalia J, Raines RT (2006) ChemBioChem 7:1375CrossRefGoogle Scholar
  121. 121.
    Govindaraju T, Jonkheijm P, Gogolin L, Schroeder H, Becker CFW, Niemeyer CM, Waldmann H (2008) Chem Commun 3723Google Scholar
  122. 122.
    Steinhagen M, Holland-Nell K, Meldal M, Beck-Sickinger AG (2011) ChemBioChem 12:2426CrossRefGoogle Scholar
  123. 123.
    Dirks AJ, Van Berkel SS, Hatzakis NS, Opsteen JA, Van Delft FL, Cornelissen JJLM, Rowan AE, Van Hest JCM, Rutjes FPJT, Nolte RJM (2005) Chem Commun 4172Google Scholar
  124. 124.
    van Dongen SFM, Teeuwen RLM, Nallani M, Van Berkel SS, Cornelissen JJLM, Nolte RJM, Van Hest JCM (2009) Bioconjug Chem 20:20CrossRefGoogle Scholar
  125. 125.
    Schoffelen S, van Eldijk MB, Rooijakkers B, Raijmakers R, Heck AJR, Van Hest JCM (2011) Chem Sci 2:701CrossRefGoogle Scholar
  126. 126.
    Debets MF, Van Berkel SS, Schoffelen S, Rutjes FPJT, Van Hest JCM, Van Delft FL (2010) Chem Commun 46:97CrossRefGoogle Scholar
  127. 127.
    Dommerholt J, Schmidt S, Temming R, Hendriks LJA, Rutjes FPJT, Van Hest JCM, Lefeber DJ, Friedl P, Van Delft FL (2010) Angew Chem Int Ed 49:9422CrossRefGoogle Scholar
  128. 128.
    Ning XH, Guo J, Wolfert MA, Boons GJ (2008) Angew Chem Int Ed 47:2253CrossRefGoogle Scholar
  129. 129.
    Jewett JC, Sletten EM, Bertozzi CR (2010) J Am Chem Soc 132:3688CrossRefGoogle Scholar
  130. 130.
    de Almeida G, Sletten EM, Nakamura H, Palaniappan KK, Bertozzi CR (2012) Angew Chem Int Ed 51:2443CrossRefGoogle Scholar
  131. 131.
    Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Miller IA, Lo A, Codelli JA, Bertozzi CR (2007) Proc Natl Acad Sci U S A 104:16793CrossRefGoogle Scholar
  132. 132.
    Kim EJ, Kang DW, Leucke HF, Bond MR, Ghosh S, Love DC, Ahn JS, Kang DO, Hanover JA (2013) Carbohydr Res 377:18CrossRefGoogle Scholar
  133. 133.
    van Geel R, Pruijn GJM, Van Delft FL, Boelens WC (2012) Bioconjug Chem 23:392CrossRefGoogle Scholar
  134. 134.
    Yang MY, Li J, Chen PR (2014) Chem Soc Rev 43:6511CrossRefGoogle Scholar
  135. 135.
    Uttamapinant C, Tangpeerachaikul A, Grecian S, Clarke S, Singh U, Slade P, Gee KR, Ting AY (2012) Angew Chem Int Ed 51:5852CrossRefGoogle Scholar
  136. 136.
    Uttamapinant C, Sanchez MI, Liu DS, Yao JZ, Ting AY (2013) Nat Protoc 8:1620CrossRefGoogle Scholar
  137. 137.
    Bevilacqua V, King M, Chaumontet M, Nothisen M, Gabillet S, Buisson D, Puente C, Wagner A, Taran F (2014) Angew Chem Int Ed 53:5872CrossRefGoogle Scholar
  138. 138.
    Lim SI, Mizuta Y, Takasu A, Kim YH, Kwon I (2014) PLoS One 9:e98403CrossRefGoogle Scholar
  139. 139.
    Besanceney-Webler C, Jiang H, Zheng TQ, Feng L, del Amo DS, Wang W, Klivansky LM, Marlow FL, Liu Y, Wu P (2011) Angew Chem Int Ed 50:8051CrossRefGoogle Scholar
  140. 140.
    Nairn NW, Shanebeck KD, Wang AJ, Graddis TJ, VanBrunt MP, Thornton KC, Grabstein K (2012) Bioconjug Chem 23:2087CrossRefGoogle Scholar
  141. 141.
    Dennler P, Chiotellis A, Fischer E, Bregeon D, Belmant C, Gauthier L, Lhospice F, Romagne F, Schibli R (2014) Bioconjug Chem 25:569CrossRefGoogle Scholar
  142. 142.
    Kim CH, Axup JY, Dubrovska A, Kazane SA, Hutchins BA, Wold ED, Smider VV, Schultz PG (2012) J Am Chem Soc 134:9918CrossRefGoogle Scholar
  143. 143.
    Wagner K, Kwakkenbos MJ, Claassen YB, Maijoor K, Bohne M, van der Sluijs KF, Witte MD, van Zoelen DJ, Cornelissen LA, Beaumont T, Bakker AQ, Ploegh HL, Spits H (2014) Proc Natl Acad Sci U S A 111:16820CrossRefGoogle Scholar
  144. 144.
    Wang AZ, Kluger R (2014) Biochemistry 53:6793CrossRefGoogle Scholar
  145. 145.
    Nischan N, Herce HD, Natala F, Bohlke N, Budisa N, Cardoso MC, Hackenberger CP (2015) Angew Chem Int Ed 54:1950CrossRefGoogle Scholar
  146. 146.
    Smith MT, Hawes AK, Bundy BC (2013) Curr Opin Biotechnol 24:620CrossRefGoogle Scholar
  147. 147.
    Patel KG, Swartz JR (2011) Bioconjug Chem 22:376CrossRefGoogle Scholar
  148. 148.
    Rhee JK, Baksh M, Nycholat C, Paulson JC, Kitagishi H, Finn MG (2012) Biomacromolecules 13:2333CrossRefGoogle Scholar
  149. 149.
    van Eldijk MB, Smits FCM, Vermue N, Debets MF, Schoffelen S, Van Hest JCM (2014) Biomacromolecules 15:2751CrossRefGoogle Scholar
  150. 150.
    Schneider D, Schneider T, Rosner D, Scheffner M, Marx A (2013) Bioorg Med Chem 21:3430CrossRefGoogle Scholar
  151. 151.
    van Treel ND, Mootz HD (2014) J Pept Sci 20:121CrossRefGoogle Scholar
  152. 152.
    Eger S, Scheffner M, Marx A, Rubini M (2010) J Am Chem Soc 132:16337CrossRefGoogle Scholar
  153. 153.
    Weikart ND, Sommer S, Mootz HD (2012) Chem Commun 48:296CrossRefGoogle Scholar
  154. 154.
    Schneider T, Schneider D, Rosner D, Malhotra S, Mortensen F, Mayer TU, Scheffner M, Marx A (2014) Angew Chem Int Ed 53:12925CrossRefGoogle Scholar
  155. 155.
    van Kasteren SI, Kramer HB, Jensen HH, Campbell SJ, Kirkpatrick J, Oldham NJ, Anthony DC, Davis BG (2007) Nature 446:1105CrossRefGoogle Scholar
  156. 156.
    Yi L, Abootorabi M, Wu YW (2011) ChemBioChem 12:2413CrossRefGoogle Scholar
  157. 157.
    Dong SL, Moroder L, Budisa N (2009) ChemBioChem 10:1149CrossRefGoogle Scholar
  158. 158.
    Milles S, Tyagi S, Banterle N, Koehler C, VanDelinder V, Plass T, Neal AP, Lemke EA (2012) J Am Chem Soc 134:5187CrossRefGoogle Scholar
  159. 159.
    Abdeljabbar DM, Piscotta FJ, Zhang SY, Link AJ (2014) Chem Commun 50:14900CrossRefGoogle Scholar
  160. 160.
    Neumann H, Wang KH, Davis L, Garcia-Alai M, Chin JW (2010) Nature 464:441CrossRefGoogle Scholar
  161. 161.
    Lin W, Du YF, Zhu YT, Chen X (2014) J Am Chem Soc 136:679CrossRefGoogle Scholar
  162. 162.
    Yang Y, Lin SX, Lin W, Chen PR (2014) ChemBioChem 15:1738CrossRefGoogle Scholar
  163. 163.
    Beatty KE, Fisk JD, Smart BP, Lu YY, Szychowski J, Hangauer MJ, Baskin JM, Bertozzi CR, Tirrell DA (2010) ChemBioChem 11:2092CrossRefGoogle Scholar
  164. 164.
    Yao JZ, Uttamapinant C, Poloukhtine A, Baskin JM, Codelli JA, Sletten EM, Bertozzi CR, Popik VV, Ting AY (2012) J Am Chem Soc 134:3720CrossRefGoogle Scholar
  165. 165.
    Borrmann A, Van Hest JCM (2014) Chem Sci 5:2123CrossRefGoogle Scholar
  166. 166.
    Hinz FI, Dieterich DC, Tirrell DA, Schuman EM (2012) ACS Chem Neurosci 3:40CrossRefGoogle Scholar
  167. 167.
    Rouhanifard SH, Nordstrom LU, Zheng TQ, Wu P (2013) Chem Soc Rev 42:4284CrossRefGoogle Scholar
  168. 168.
    Hong V, Steinmetz NF, Manchester M, Finn MG (2010) Bioconjug Chem 21:1912CrossRefGoogle Scholar
  169. 169.
    del Amo DS, Wang W, Jiang H, Besanceney C, Yan AC, Levy M, Liu Y, Marlow FL, Wu P (2010) J Am Chem Soc 132:16893CrossRefGoogle Scholar
  170. 170.
    Laughlin ST, Baskin JM, Amacher SL, Bertozzi CR (2008) Science 320:664CrossRefGoogle Scholar
  171. 171.
    Jiang H, Zheng TQ, Lopez-Aguilar A, Feng L, Kopp F, Marlow FL, Wu P (2014) Bioconjug Chem 25:698CrossRefGoogle Scholar
  172. 172.
    Laughlin ST, Bertozzi CR (2009) ACS Chem Biol 4:1068CrossRefGoogle Scholar
  173. 173.
    Chang PV, Prescher JA, Sletten EM, Baskin JM, Miller IA, Agard NJ, Lo A, Bertozzi CR (2010) Proc Natl Acad Sci U S A 107:1821CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Center for Evolutionary Chemical BiologyUniversity of CopenhagenCopenhagenDenmark

Personalised recommendations