Alkyne-Azide Reactions

Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations

Volumn 9783527335053, Issue , 2015, Pages 113-142

  Schoffelen, Sanne ^a   Meldal, Morten ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Bio labeling; Catalysis; Click ligands; Click optimization; Click reaction; Cu free; CuAAC; Mechanism; Solvent effect

Indexed keywords

SOLVENTS;

BIO-LABELING; CLICK LIGAND; CLICK OPTIMIZATION; CLICK REACTION; CONDITION; CU-FREE; CUAAC; LABELINGS; OPTIMISATIONS; SOLVENT EFFECTS;

LIGANDS;

EID: 84926500956     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527677894.ch5     Document Type: Chapter

References (168)

1. Kolb, H.C., Finn, M.G., and Sharpless, K.B. (2001) Angew. Chem. Int. Ed., 40, 2004-2021.
2. Tornøe, C.W. and Meldal, M. (2001) in Peptides 2001, Proceedings American Peptide Symposium (eds M. Lebl and R.A. Houghten), American Peptide Society and Kluwer Academic Publishers, San Diego, CA, pp. 263-264.
3. Huisgen, R. (1989) Pure Appl. Chem., 61, 613-678.
4. Huisgen, R., Szeimies, G., and Moebius, L. (1967) Chem. Ber., 100, 2494-2507.
5. Tornøe, C.W., Christensen, C., and Meldal, M. (2002) J. Org. Chem., 67, 3057-3064.
6. Rostovtsev, V.V., Green, L.G., Fokin, V.V., and Barry Sharpless, K. (2002) Angew. Chem. Int. Ed., 41, 2596-2599.
7. Breinbauer, R. and Köhn, M. (2003) ChemBioChem, 4, 1147-1149.
8. Speers, A.E., Adam, G.C., and Cravatt, B.F. (2003) J. Am. Chem. Soc., 125, 4686-4687.
9. Beatty, K.E., Xie, F., Wang, Q., and Tirrell, D.A. (2005) J. Am. Chem. Soc., 127, 14150-14151.
10. Beatty, K.E., Liu, J.C., Xie, F., Dieterich, D.C., Schuman, E.M., Wang, Q., and Tirrell, D.A. (2006) Angew. Chem. Int. Ed., 45, 7364-7367.
11. Deiters, A. and Schultz, P.G. (2005) Bioorg. Med. Chem. Lett., 15, 1521-1524.
12. Golas, P.L., Tsarevsky, N.V., Sumerlin, B.S., and Matyjaszewski, K. (2006) Macromolecules, 39, 6451-6457.
13. Wu, P. and Fokin, V.V. (2007) Aldrich Chim. Acta, 40, 7-17.
14. Michael, A. (1893) J. Prakt. Chem., 48, 94-95.
15. Lwowski, W. (1984) in 1,3-Dipolar Cycloaddition Chemistry (ed. A. Padwa), John Wiley & Sons, Inc., New York, pp. 559-651.
16. Boren, B.C., Narayan, S., Rasmussen, L.K., Zhang, L., Zhao, H., Lin, Z., Jia, G., and Fokin, V.V. (2008) J. Am. Chem. Soc., 130, 8923-8930.
17. Boz, E. and Tüzün, N.S. (2013) J. Organomet. Chem., 724, 167-176.
18. Kolb, H.C. and Sharpless, K.B. (2003) Drug Discovery Today, 8, 1128-1137.
19. Bock, V.D., Hiemstra, H., and Van Maarseveen, J.H. (2006) Eur. J. Org. Chem., 51-68.
20. Binder, W.H. and Sachsenhofer, R. (2007) Macromol. Rapid Commun., 28, 15-54.
21. Lutz, J.F. (2007) Angew. Chem. Int. Ed., 46, 1018-1025.
22. Gil, M.V., Arévalo, M.J., and López, Ó. (2007) Synthesis, 11, 1589-1620.
23. Li, Y., Ju, Y., and Zhao, Y.F. (2006) Chin. J. Org. Chem., 26, 1640-1646.
24. Moses, J.E. and Moorhouse, A.D. (2007) Chem. Soc. Rev., 36, 1249-1262.
25. Meldal, M. and Tornøe, C.W. (2008) Chem. Rev., 108, 2952-3015.
26. Meldal, M. (2008) Macromol. Rapid Commun., 29, 1016-1051.
27. Tornøe, C.W. and Meldal, M. (2010) in Organic Azides: Syntheses and Applications (eds S. Bräse and K. Banert), John Wiley & Sons, Ltd, Chichester, pp. 285-310.
28. Buckley, B.R. and Heaney, H. (2012) Click Triazoles, Springer, pp. 1-29.
29. Jewett, J.C. and Bertozzi, C.R. (2010) Chem. Soc. Rev., 39, 1272-1279.
30. Jones, G.O., Ess, D.H., and Houk, K.N. (2005) Helv. Chim. Acta, 88, 1702-1710.
31. Pérez, P., Domingo, L.R., Aurell, M.J., and Contreras, R. (2003) Tetrahedron, 59, 3117-3125.
32. Worrell, B.T., Malik, J.A., and Fokin, V.V. (2013) Science, 340, 457-460.
33. Kamata, K., Nakagawa, Y., Yamaguchi, K., and Mizuno, N. (2008) J. Am. Chem. Soc., 130, 15304-15310.
34. Berg, R., Straub, J., Schreiner, E., Mader, S., Rominger, F., and Straub, B.F. (2012) Adv. Synth. Catal., 354, 3445-3450.
35. Straub, B.F. (2007) Chem. Commun., 3868-3870.
36. Ahlquist, M. and Fokin, V.V. (2007) Organometallics, 26, 4389-4391.
37. Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V.V., Noodleman, L., Sharpless, K.B., and Fokin, V.V. (2005) J. Am. Chem. Soc., 127, 210-216.
38. Özen, C. and Tüzün, N.Ç. (2012) J. Mol. Graphics Modell., 34, 101-107.
39. Rodionov, V.O., Fokin, V.V., and Finn, M.G. (2005) Angew. Chem. Int. Ed., 44, 2210-2215.
40. Chen, F.F. and Wang, F. (2009) Molecules, 14, 2656-2668.
41. Cenini, S., Gallo, E., Caselli, A., Ragaini, F., Fantauzzi, S., and Piangiolino, C. (2006) Coord. Chem. Rev., 250, 1234-1253.
42. Jagasia, R., Holub, J.M., Bollinger, M., Kirshenbaum, K., and Finn, M.G. (2009) J. Org. Chem., 74, 2964-2974.
43. Roice, M., Johannsen, I., and Meldal, M. (2004) QSAR & Comb. Sci., 23, 662-673.
44. Le Chevalier, I.A., Papini, A.M., Chorev, M., and Rovero, P. (2009) J. Pept. Sci., 15, 451-454.
45. Holland-Nell, K. and Meldal, M. (2011) Angew. Chem. Int. Ed., 123, 5310-5312.
46. Ingale, S. and Dawson, P.E. (2011) Org. Lett., 13, 2822-2825.
47. Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P.,Wilhelmsson, L.M., and Brown, T. (2007) J. Am. Chem. Soc., 129, 6859-6864.
48. Kislukhin, A.A., Hong, V.P., Breitenkamp, K.E., and Finn, M.G. (2013) Bioconjugate Chem., 24, 684-689.
49. Yuan, Z., Kuang, G.C., Clark, R.J., and Zhu, L. (2012) Org. Lett., 14, 2590-2593.
50. Ingale, S.A. and Seela, F. (2013) J. Org. Chem., 78, 3394-3399.
51. Uttamapinant, C., Tangpeerachaikul, A., Grecian, S., Clarke, S., Singh, U., Slade, P., Gee, K.R., and Ting, A.Y. (2012) Angew. Chem. Int. Ed., 124, 5954-5958.
52. Uttamapinant, C., Sanchez, M.I., Liu, D.S., Yao, J.Z., and Ting, A.Y. (2013) Nat. Protoc., 8, 1620-1634.
53. Ryu, E.H. and Zhao, Y. (2005) Org. Lett., 7, 1035-1037.
54. Sumerlin, B.S., Tsarevsky, N.V., Louche, G., Lee, R.Y., and Matyjaszewski, K. (2005) Macromolecules, 38, 7540-7545.
55. Paredes, E. and Das, S.R. (2012) Bioorg. Med. Chem. Lett., 22, 5313-5316.
56. Zhang, Y.F., Han, X.D., Ren, C.Q., and Zhao, Y.L. (2013) Synth. Commun., 43, 2119-2126.
57. Grignard, B., Schmeits, S., Riva, R., Detrembleur, C., Lecomte, P., and Jérôme, C. (2009) Green Chem., 11, 1525-1529.
58. Siemsen, P., Livingston, R.C., and Diederich, F. (2000) Angew. Chem. Int. Ed., 39, 2632-2657.
59. Angell, Y. and Burgess, K. (2007) Angew. Chem. Int. Ed., 46, 3649-3651.
60. Ackermann, L., Potukuchi, H.K., Landsberg, D., and Vicente, R. (2008) Org. Lett., 10, 3081-3084.
61. Yang, D., Fu, N., Liu, Z., Li, Y., and Chen, B. (2007) Synlett, 278-282.
62. Wu, Y.M., Deng, J., and Chen, Q.Y. (2006) Synlett, 645-647.
63. Wu, Y.M., Deng, J., Li, Y., and Chen, Q.Y. (2005) Synthesis, 1314-1318.
64. Spiteri, C. and Moses, J.E. (2010) Angew. Chem. Int. Ed., 49, 31-33.
65. Hein, J.E., Tripp, J.C., Krasnova, L.B., Sharpless, K.B., and Fokin, V.V. (2009) Angew. Chem. Int. Ed., 121, 8162-8165.
66. Stefani, H.A., Silva, N.C.S., Vasconcelos, S.N.S., Manarin, F., and Souza, F.B. (2013) Tetrahedron Lett., 54, 2809-2812.
67. Partyka, D.V., Updegraff, J.B. III, Zeller, M., Hunter, A.D., and Gray, T.G. (2007) Organometallics, 26, 183-186.
68. Partyka, D.V., Gao, L., Teets, T.S., Updegraff, J.B. III, Deligonul, N., and Gray, T.G. (2009) Organometallics, 28, 6171-6182.
69. Gray, T.G., Heckler, J.E., Deligonul, N., and Rheingold, A.L. (2013) Chem. Commun., 49, 5990-5992.
70. Li, L., Zhang, G., Zhu, A., and Zhang, L. (2008) J. Org. Chem., 73, 3630-3633.
71. Yoo, E.J., Ahlquist, M., Kim, S.H., Bae, I., Fokin, V.V., Sharpless, K.B., and Chang, S. (2007) Angew. Chem. Int. Ed., 46, 1730-1733.
72. Yoo, E.J., Bae, I., Cho, S.H., Han, H., and Chang, S. (2006) Org. Lett., 8, 1347-1350.
73. Bertrand, P. and Gesso, J.P. (2007) J. Org. Chem., 72, 3596-3599.
74. Zhang, X., Li, H., You, L., Tang, Y., and Hsung, R.P. (2006) Adv. Synth. Catal., 348, 2437-2442.
75. Zhang, X., Hsung, R.P., and You, L. (2006) Org. Biomol. Chem., 4, 2679-2682.
76. Lewis, W.G., Magallon, F.G., Fokin, V.V., and Finn, M.G. (2004) J. Am. Chem. Soc., 126, 9152-9153.
77. Evans, R.A. (2007) Aust. J. Chem., 60, 384-395.
78. Finn, M.G. and Fokin, V.V. (2010) in Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) in Catalysis without Precious Metals (ed. R.M. Bullock), Wiley-VCH Verlag GmbH, pp. 235-260.
79. Nandivada, H., Jiang, X., and Lahann, J. (2007) Adv. Mater., 19, 2197-2208.
80. Jung, N. and Bräse, S. (2013) Kirk-Othmer Encycl. Chem. Technol., 1-43.
81. Crowley, J.D., Lee, A.L., and Kilpin, K.J. (2011) Aust. J. Chem., 64, 1118-1132.
82. Donnelly, P.S., Zanatta, S.D., Zammit, S.C., White, J.M., and Williams, S.J. (2008) Chem. Commun., 2459-2461.
83. Hohloch, S., Scheiffele, D., and Sarkar, B. (2013) Eur. J. Inorg. Chem., 2013, 3956-3965.
84. Díez-González, S. and Nolan, S.P. (2008) Angew. Chem. Int. Ed., 120, 9013-9016.
85. Rodionov, V.O., Presolski, S.I., Gardinier, S., Lim, Y.H., and Finn, M.G. (2007) J. Am. Chem. Soc., 129, 12696-12704.
86. Candelon, N., Lastécouères, D., Diallo, A.K., Aranzaes, J.R., Astruc, D., and Vincent, J.M. (2008) Chem. Commun., 741-743.
87. Lee, B.H., Wu, C.C., Fang, X., Liu, C.W., and Zhu, J.L. (2013) Catal. Lett., 143, 1-6.
88. Özçubukçu, S., Ozkal, E., Jimeno, C., and Pericas, M.A. (2009) Org. Lett., 11, 4680-4683.
89. Fabbrizzi, P., Cicchi, S., Brandi, A., Sperotto, E., and van Koten, G. (2009) Eur. J. Org. Chem., 2009, 5423-5430.
90. Messaoudi, S., Gabillet, M., Brion, J.D., and Alami, M. (2013) Appl. Organomet. Chem., 27, 155-158.
91. Ozkal, E., Özçubukçu, S., Jimeno, C., and Pericas, M.A. (2012) Catal. Sci. Technol., 2, 195-200.
92. Kuang, G.C., Guha, P.M., Brotherton, W.S., Simmons, J.T., Stankee, L.A., Nguyen, B.T., Clark, R.J., and Zhu, L. (2011) J. Am. Chem. Soc., 133, 13984-14001.
93. Díez-González, S., Stevens, E.D., and Nolan, S.P. (2008) Chem. Commun., 4747-4749.
94. Díez-González, S. and Nolan, S.P. (2007) Synlett, 2158-2167.
95. Díez-González, S., Correa, A., Cavallo, L., and Nolan, S.P. (2006) Chem.-Eur. J., 12, 7558-7564.
96. Gibard, C., Ibrahim, H., Gautier, A., and Cisnetti, F. (2013) Organometallics, 32, 4279-4283.
97. Hohloch, S., Sarkar, B., Nauton, L., Cisnetti, F., and Gautier, A. (2013) Tetrahedron Lett., 54, 1808-1812.
98. Gaulier, C., Legeret, B., Delmas, A.F., Aucagne, V., Cisnetti, F., and Gautier, A. (2012) Chem. Commun., 48, 4005-4007.
99. Gibard, C., Avignant, D., Cisnetti, F., and Gautier, A. (2012) Organometallics, 31, 7902-7908.
100. Teyssot, M.-L., Nauton, L., Canet, J.-L., Cisnetti, F., Chevry, A., and Gautier, A. (2010) Eur. J. Org. Chem., 2010, 3507-3515.
101. Teyssot, M.-L., Chevry, A., Traïkia, M., El-Ghozzi, M., Avignant, D., and Gautier, A. (2009) Chem.-Eur. J., 15, 6322-6326.
102. Gu, S., Huang, J., Liu, X., Liu, H., Zhou, Y., and Xu, W. (2012) Inorg. Chem. Commun., 21, 168-172.
103. Ison, E.A. and Ison, A. (2012) J. Chem. Educ., 89, 1575-1577.
104. Donnelly, K.F., Petronilho, A., and Albrecht, M. (2013) Chem. Commun., 49, 1145-1159.
105. Liu, M. and Reiser, O. (2011) Org. Lett., 13, 1102-1105.
106. Hansen, T.S., Daugaard, A.E., Hvilsted, S., and Larsen, N.B. (2009) Adv. Mater., 21, 4483-4486.
107. Nicosia, C., Krabbenborg, S.O., Chen, P., and Huskens, J. (2013) J. Mater. Chem. B, 1, 5417-5428.
108. Adzima, B.J., Tao, Y., Kloxin, C.J., DeForest, C.A., Anseth, K.S., and Bowman, C.N. (2011) Nat. Chem., 3, 256-259.
109. Sandmann, B., Happ, B., Vitz, J., Hager, M., Moszner, N., Burtscher, P., and Schubert, U.S. (2013) Polym. Chem., 4, 3938-3942.
110. Gong, T., Adzima, B.J., Baker, N.H., and Bowman, C.N. (2013) Adv. Mater., 25, 2024-2028.
111. Orain, C., Le Poul, N., Gomila, A., Kerbaol, J.-M., Cosquer, N., Reinaud, O., Conan, F., and Le Mest, Y. (2012) Chem.-Eur. J., 18, 594-602.
112. Lallana, E., Riguera, R., and Fernandez-Megia, E. (2011) Angew. Chem. Int. Ed., 50, 8794-8804.
113. Canalle, L.A., Lowik, D.W.P.M., and Van Hest, J.C.M. (2010) Chem. Soc. Rev., 39, 329-353.
114. Sletten, E.M. and Bertozzi, C.R. (2009) Angew. Chem. Int. Ed., 48, 6974-6998.
115. Thirumurugan, P., Matosiuk, D., and Jozwiak, K. (2013) Chem. Rev., 113, 4905-4979.
116. Kim, C.H., Axup, J.Y., and Schultz, P.G. (2013) Curr. Opin. Chem. Biol., 17, 412-419.
117. Nairn, N.W., Shanebeck, K.D., Wang, A.J., Graddis, T.J., VanBrunt, M.P., Thornton, K.C., and Grabstein, K. (2012) Bioconjugate Chem., 23, 2087-2097.
118. Park, S., Gildersleeve, J.C., Blixt, O., and Shin, I. (2013) Chem. Soc. Rev., 42, 4310-4326.
119. Palomo, J.M. (2013) Curr. Org. Chem., 17, 691-700.
120. Ran, Q., Peng, R., Liang, C., Ye, S.Q., Xian, Y.Z., Zhang, W.J., and Jin, L.T. (2011) Talanta, 83, 1381-1385.
121. Baradel, N., Fort, S., Halila, S., Badi, N., and Lutz, J.F. (2013) Angew. Chem. Int. Ed., 52, 2335-2339.
122. Amir, L., Carnally, S.A., Rayo, J., Rosenne, S., Yerushalmi, S.M., Schlesinger, O., Meijler, M.M., and Alfonta, L. (2013) J. Am. Chem. Soc., 135, 70-73.
123. Patel, K.G. and Swartz, J.R. (2011) Bioconjugate Chem., 22, 376-387.
124. Rubino, F.A., Oum, Y.H., Rajaram, L., Chu, Y., and Carrico, I.S. (2012) JoVE, e4246.
125. Duckworth, B.P., Chen, Y., Wollack, J.W., Sham, Y., Mueller, J.D., Taton, T.A., and Distefano, M.D. (2007) Angew. Chem. Int. Ed., 46, 8819-8822.
126. Ngo, J.T. and Tirrell, D.A. (2011) Acc. Chem. Res., 44, 677-685.
127. Chang, P.V. and Bertozzi, C.R. (2012) Chem. Commun., 48, 8864-8879.
128. Rouhanifard, S.H., Nordstrom, L.U., Zheng, T.Q., and Wu, P. (2013) Chem. Soc. Rev., 42, 4284-4296.
129. Hsu, T.L., Hanson, S.R., Kishikawa, K., Wang, S.K., Sawa, M., and Wong, C.H. (2007) Proc. Natl. Acad. Sci. U.S.A., 104, 2614-2619.
130. Dumont, A., Malleron, A., Awwad, M., Dukan, S., and Vauzeilles, B. (2012) Angew. Chem. Int. Ed., 51, 3143-3146.
131. Salic, A. and Mitchison, T.J. (2008) Proc. Natl. Acad. Sci. U.S.A., 105, 2415-2420.
132. Jao, C.Y. and Salic, A. (2008) Proc. Natl. Acad. Sci. U.S.A., 105, 15779-15784.
133. Neef, A.B. and Schultz, C. (2009) Angew. Chem. Int. Ed., 48, 1498-1500.
134. Thiele, C., Papan, C., Hoelper, D., Kusserow, K., Gaebler, A., Schoene, M., Piotrowitz, K., Lohmann, D., Spandl, J., Stevanovic, A., Shevchenko, A., and Kuerschner, L. (2012) ACS Chem. Biol., 7, 2004-2011.
135. Peters, W.,Willnow, S., Duisken, M., Kleine, H., Macherey, T., Duncan, K.E., Litchfield, D.W., Luscher, B., and Weinhold, E. (2010) Angew. Chem. Int. Ed., 49, 5170-5173.
136. van Dongen, S.F.M., Teeuwen, R.L.M., Nallani, M., Van Berkel, S.S., Cornelissen, J.J.L.M., Nolte, R.J.M., and Van Hest, J.C.M. (2009) Bioconjugate Chem., 20, 20-23.
137. Schoffelen, S., van Eldijk, M.B., Rooijakkers, B., Raijmakers, R., Heck, A.J.R., and Van Hest, J.C.M. (2011) Chem. Sci., 2, 701-705.
138. Matsumoto, T., Tanaka, T., and Kondo, A. (2012) Biotechnol. J., 7, 1137-1146.
139. van Geel, R., Debets, M.F., Lowik, D.W.P.M., Pruijn, G.J.M., and Boelens, W.C. (2012) Amino Acids, 43, 1251-1263.
140. Fernandez-Suarez, M., Baruah, H., Martinez-Hernandez, L., Xie, K.T., Baskin, J.M., Bertozzi, C.R., and Ting, A.Y. (2007) Nat. Biotechnol., 25, 1483-1487.
141. Witte, M.D., Cragnolini, J.J., Dougan, S.K., Yoder, N.C., Popp, M.W., and Ploegh, H.L. (2012) Proc. Natl. Acad. Sci. U.S.A., 109, 11993-11998.
142. Johnson, J.A., Lu, Y.Y., Van Deventer, J.A., and Tirrell, D.A. (2010) Curr. Opin. Chem. Biol., 14, 774-780.
143. Davis, L. and Chin, J.W. (2012) Nat. Rev. Mol. Cell Biol., 13, 168-182.
144. Liu, C.C. and Schultz, P.G. (2010) Annu. Rev. Biochem., 79, 413-444.
145. Jao, C.Y., Roth, M., Welti, R., and Salic, A. (2009) Proc. Natl. Acad. Sci. U.S.A., 106, 15332-15337.
146. Hang, H.C., Wilson, J.P., and Charron, G. (2011) Acc. Chem. Res., 44, 699-708.
147. Hannoush, A.N. and Sun, J. (2010) Nat. Chem. Biol., 6, 498-506.
148. Gierlich, J., Burley, G.A., Gramlich, P.M.E., Hammond, D.M., and Carell, T. (2006) Org. Lett., 8, 3639-3642.
149. Seo, T.S., Li, Z.M., Ruparel, H., and Ju, J.Y. (2003) J. Org. Chem., 68, 609-612.
150. Rao, H., Tanpure, A.A., Sawant, A.A., and Srivatsan, S.G. (2012) Nat. Protoc., 7, 1097-1112.
151. Ishizuka, T., Kimoto, M., Sato, A., and Hirao, I. (2012) Chem. Commun., 48, 10835-10837.
152. Wang, Q., Chan, T.R., Hilgraf, R., Fokin, V.V., Sharpless, K.B., and Finn, M.G. (2003) J. Am. Chem. Soc., 125, 3192-3193.
153. Agard, N.J., Prescher, J.A., and Bertozzi, C.R. (2004) J. Am. Chem. Soc., 126, 15046-15047.
154. Baskin, J.M., Prescher, J.A., Laughlin, S.T., Agard, N.J., Chang, P.V., Miller, I.A., Lo, A., Codelli, J.A., and Bertozzi, C.R. (2007) Proc. Natl. Acad. Sci. U.S.A., 104, 16793-16797.
155. Jewett, J.C., Sletten, E.M., and Bertozzi, C.R. (2010) J. Am. Chem. Soc., 132, 3688-3690.
156. Ning, X.H., Guo, J.,Wolfert, M.A., and Boons, G.J. (2008) Angew. Chem. Int. Ed., 47, 2253-2255.
157. Debets, M.F., Van Berkel, S.S., Schoffelen, S., Rutjes, F.P.J.T., Van Hest, J.C.M., and Van Delft, F.L. (2010) Chem. Commun., 46, 97-99.
158. Dommerholt, J., Schmidt, S., Temming, R., Hendriks, L.J.A., Rutjes, F.P.J.T., Van Hest, J.C.M., Lefeber, D.J., Friedl, P., and Van Delft, F.L. (2010) Angew. Chem. Int. Ed., 49, 9422-9425.
159. Hong, V., Presolski, S.I., Ma, C., and Finn, M.G. (2009) Angew. Chem. Int. Ed., 48, 9879-9883.
160. Hong, V., Steinmetz, N.F., Manchester, M., and Finn, M.G. (2010) Bioconjugate Chem., 21, 1912-1916.
161. del Amo, D.S., Wang, W., Jiang, H., Besanceney, C., Yan, A.C., Levy, M., Liu, Y., Marlow, F.L., and Wu, P. (2010) J. Am. Chem. Soc., 132, 16893-16899.
162. Besanceney-Webler, C., Jiang, H., Zheng, T.Q., Feng, L., del Amo, D.S., Wang, W., Klivansky, L.M., Marlow, F.L., Liu, Y., and Wu, P. (2011) Angew. Chem. Int. Ed., 50, 8051-8056.
163. Kennedy, D.C., McKay, C.S., Legault, M.C., Danielson, D.C., Blake, J.A., Pegoraro, A.F., Stolow, A., Mester, Z., and Pezacki, J.P. (2011) J. Am. Chem. Soc., 133, 17993-18001.
164. Beatty, K.E., Fisk, J.D., Smart, B.P., Lu, Y.Y., Szychowski, J., Hangauer, M.J., Baskin, J.M., Bertozzi, C.R., and Tirrell, D.A. (2010) ChemBioChem, 11, 2092-2095.
165. Borrmann, A., Milles, S., Plass, T., Dommerholt, J., Verkade, J.M.M., Wiessler, M., Schultz, C., Van Hest, J.C.M., Van Delft, F.L., and Lemke, E.A. (2012) ChemBioChem, 13, 2094-2099.
166. Lo Conte, M., Staderini, S., Marra, A., Sanchez-Navarro, M., Davis, B.G., and Dondoni, A. (2011) Chem. Commun., 47, 11086-11088.
167. van Geel, R., Pruijn, G.J.M., van Delft, F.L., and Boelens, W.C. (2012) Bioconjugate Chem., 23, 392-398.
168. Kim, E.J., Kang, D.W., Leucke, H.F., Bond, M.R., Ghosh, S., Love, D.C., Ahn, J.S., Kang, D.O., and Hanover, J.A. (2013) Carbohydr. Res., 377, 18-27.