Pure and Applied Chemistry

Pure Appl. Chem., 2013, Vol. 85, No. 7, pp. 1499-1513

http://dx.doi.org/10.1351/PAC-CON-13-01-08

Published online 2013-05-23

Photo-click chemistry strategies for spatiotemporal control of metal-free ligation, labeling, and surface derivatization

References

• 1. H. C. Kolb, M. G. Finn, K. B. Sharpless. Angew. Chem., Int. Ed. 40, 2004 (2001). (http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5)
• 2a. L. Nebhani, C. Barner-Kowollik. Adv. Mater. 21, 3442 (2009). (http://dx.doi.org/10.1002/adma.200900238)
• 2b. L. S. Wong, F. Khan, J. Micklefield. Chem. Rev. 109, 4025 (2009). (http://dx.doi.org/10.1021/cr8004668)
• 2c. B. D. Ratner. In Biomaterials Science: An Introduction to Materials in Medicine, A. S. Hoffman, F. J. Schoen, J. E. Lemons (Eds.), Academic Press, San Diego (2004).
• 3a. R. K. Iha, K. L. Wooley, A. M. Nyström, D. J. Burke, M. J. Kade, C. J. Hawker. Chem. Rev. 109, 5620 (2009). (http://dx.doi.org/10.1021/cr900138t)
• 3b. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless. Angew. Chem., Int. Ed. 41, 2596 (2002). (http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4)
• 3c. J. E. Hein, V. V. Fokin. Chem. Soc. Rev. 39, 1302 (2010). (http://dx.doi.org/10.1039/b904091a)
• 3d. S. K. Mamidyala, M. G. Finn. Chem. Soc. Rev. 39, 1252 (2010). (http://dx.doi.org/10.1039/b901969n)
• 3e. S. G. Im, K. W. Bong, B.-S. Kim, S. H. Baxamusa, P. T. Hammond, P. S. Doyle, K. K. Gleason. J. Am. Chem. Soc. 130, 14424 (2008). (http://dx.doi.org/10.1021/ja806030z)
• 4a. S. Fleischmann, K. Hinrichs, U. Oertel, S. Reichelt, K.-J. Eichhorn, B. Voit. Macromol. Rapid Commun. 29, 1177 (2008). (http://dx.doi.org/10.1002/marc.200800095)
• 4b. D. Fournier, R. Hoogenboom, U. S. Schubert. Chem. Rev. Soc. 36, 1369 (2007). (http://dx.doi.org/10.1039/b700809k)
• 4c. X.-L. Sun, C. L. Stabler, C. S. Cazalis, E. L. Chaikof. Bioconjugate Chem. 17, 52 (2006). (http://dx.doi.org/10.1021/bc0502311)
• 4d. O. Michel, B. J. Ravoo. Langmuir 24, 12116 (2008). (http://dx.doi.org/10.1021/la802304w)
• 4e. S.-Y. Ku, K.-T. Wong, A. Bard. J. Am. Chem. Soc. 130, 2392 (2008). (http://dx.doi.org/10.1021/ja078183d)
• 4f. J. E. Moses, A. D. Moorhouse. Chem. Soc. Rev. 36, 1242 (2007). (http://dx.doi.org/10.1039/b613014n)
• 4g. H. Nandivada, X. Jiang, J. Lahann. Adv. Mater. 19, 2197 (2007). (http://dx.doi.org/10.1002/adma.200602739)
• 5a. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless, V. V. Fokin. Angew. Chem., Int. Ed. 43, 3928 (2004). (http://dx.doi.org/10.1002/anie.200454078)
• 5b. S. Punna, E. Kaltgrad, M. G. Finn. Bioconjugate Chem. 16, 1536 (2005). (http://dx.doi.org/10.1021/bc0501496)
• 5c. S. Punna, J. Kuzelka, Q. Wang, M. G. Finn. Angew. Chem., Int. Ed. 44, 2215 (2005). (http://dx.doi.org/10.1002/anie.200461656)
• 5d. J. A. Johnson, D. R. Lewis, D. D. Diaz, M. G. Finn, J. T. Koberstein, N. J. Turro. J. Am. Chem. Soc. 128, 6564 (2006). (http://dx.doi.org/10.1021/ja0612910)
• 5e. R. J. Thibault, K. Takizawa, P. Lowenheilm, B. Helms, J. L. Mynar, J. M. J. Frechet, C. J. Hawker. J. Am. Chem. Soc. 128, 12084 (2006). (http://dx.doi.org/10.1021/ja0648209)
• 5f. M. J. Joralemon, R. K. O’Reilly, C. J. Hawker, K. L. Wooley. J. Am. Chem. Soc. 127, 16892 (2005). (http://dx.doi.org/10.1021/ja053919x)
• 5g. M. Malkoch, R. J. Thibault, E. Drockenmuller, M. Messerschmidt, B. Voit, T. P. Russell, C. J. Hawker. J. Am. Chem. Soc. 127, 14942 (2005). (http://dx.doi.org/10.1021/ja0549751)
• 6a. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn. J. Am. Chem. Soc. 125, 3192 (2003). (http://dx.doi.org/10.1021/ja021381e)
• 6b. E. Strable, D. E. Prasuhn, A. K. Udit, S. Brown, A. J. Link, J. T. Ngo, G. Lander, J. Quispe, C. S. Potter, B. Carragher, D. A. Tirrell, M. G. Finn. Bioconjugate Chem. 19, 866 (2008). (http://dx.doi.org/10.1021/bc700390r)
• 7a. G. von Maltzahn, Y. Ren, J.-H. Park, D.-H. Min, V. R. Kotamraju, J. Jayakumar, V. Fogal, M. J. Sailor, E. Ruoslahti, S. N. Bhatia. Bioconjugate Chem. 19, 1570 (2008). (http://dx.doi.org/10.1021/bc800077y)
• 7b. H. C. Kolb, K. B. Sharpless. Drug Discov. Today 8, 1128 (2003). (http://dx.doi.org/10.1016/S1359-6446(03)02933-7)
• 7c. K. B. Sharpless, R. Manetsch. Exp. Opin. Drug Discov. 1, 525 (2006). (http://dx.doi.org/10.1517/17460441.1.6.525)
• 8a. L. M. Gaetke, C. K. Chow. Toxicology 189, 147 (2003). (http://dx.doi.org/10.1016/S0300-483X(03)00159-8)
• 8b. C. J. Burrows, J. G. Muller. Chem. Rev. 98, 1109 (1998). (http://dx.doi.org/10.1021/cr960421s)
• 8c. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn. J. Am. Chem. Soc. 125, 3192 (2003). (http://dx.doi.org/10.1021/ja021381e)
• 9a. J. M. Baskin, J. A. Prescher, S. T. Laughlin, N. J. Agard, P. V. Chang, I. A. Miller, A. Lo, J. A. Codelli, C. R. Bertozzi. Proc. Natl. Acad. Sci. USA 104, 16793 (2007). (http://dx.doi.org/10.1073/pnas.0707090104)
• 9b. E. M. Sletten, C. R. Bertozzi. Org. Lett. 10, 3097 (2008). (http://dx.doi.org/10.1021/ol801141k)
• 9c. J. A. Codelli, J. M. Baskin, N. J. Agard, C. R. Bertozzi. J. Am. Chem. Soc. 130, 11486 (2008). (http://dx.doi.org/10.1021/ja803086r)
• 9d. J. Dommerholt, S. Schmidt, R. Temming, L. J. A. Hendriks, F. P. J. T. Rutjes, J. C. M. van Hest, D. J. Lefeber, P. Friedl, F. L. van Delft. Angew. Chem., Int. Ed. 49, 9422 (2010). (http://dx.doi.org/10.1002/anie.201003761)
• 10. X. Ning, J. Guo, M. A. Wolfert, G.-J. Boons. Angew. Chem., Int. Ed. 47, 2253 (2008). (http://dx.doi.org/10.1002/anie.200705456)
• 11a. J. C. Jewett, E. M. Sletten, C. R. Bertozzi. J. Am. Chem. Soc. 132, 3688 (2010). (http://dx.doi.org/10.1021/ja100014q)
• 11b. M. F. Debets, S. S. van Berkel, S. Schoffelen, F. P. J. T. Rutjes, J. C. M. van Hest, F. L. van Delft. Chem. Commun. 46, 97 (2010). (http://dx.doi.org/10.1039/b917797c)
• 11c. A. Kuzmin, A. Poloukhtine, M. Wolfert, V. V. Popik. Bioconjugate Chem. 21, 2076 (2010). (http://dx.doi.org/10.1021/bc100306u)
• 12. G. de Almeida, E. M. Sletten, H. Nakamura, K. K. Palaniappan, C. R. Bertozzi. Angew. Chem., Int. Ed. 51, 2443 (2012). (http://dx.doi.org/10.1002/anie.201106325)
• 13a. D. H. Ess, G. O. Jones, K. N. Houk. Org. Lett. 10, 1633 (2008). (http://dx.doi.org/10.1021/ol8003657)
• 13b. J. C. Jewett, C. R. Bertozzi. Chem. Soc. Rev. 39, 1272 (2010). (http://dx.doi.org/10.1039/b901970g)
• 13c. M. F. Debets, C. W. J. van der Doelen, F. P. J. T. Rutjes, F. L. van Delft. ChemBioChem 11, 1168 (2010). (http://dx.doi.org/10.1002/cbic.201000064)
• 13d. M. F. Debets, S. S. van Berkel, J. Dommerholt, A. J. Dirks, A. F. P. J. T. Rutjes, F. L. van Delft. Acc. Chem. Res. 44, 805 (2011). (http://dx.doi.org/10.1021/ar200059z)
• 13e. E. M. Sletten, C. R. Bertozzi. Acc. Chem. Res. 44, 666 (2011). (http://dx.doi.org/10.1021/ar200148z)
• 14. D. B. Ramachary, C. F. Barbas. Chem.—Eur. J. 10, 5323 (2004). (http://dx.doi.org/10.1002/chem.200400597)
• 15a. H. Durmaz, B. Colakoglu, U. Tunca, G. Hizal. J. Polym. Sci., Part A 44, 1667 (2006). (http://dx.doi.org/10.1002/pola.21275)
• 15b. A. Dag, H. Durmaz, G. Hizal, U. Tunca. J. Polym. Sci., Part A 46, 302 (2008). (http://dx.doi.org/10.1002/pola.22381)
• 15c. B. Gacal, H. Durmaz, M. A. Tasdelen, G. Hizal, U. Tunca, Y. Yagci, A. L. Demirel. Macromolecules 39, 5330 (2006). (http://dx.doi.org/10.1021/ma060690c)
• 15d. J. L. Delgado, P. de la Cruz, F. Langa, A. Urbina, J. Casado, J. T. Lopez Navarrete. Chem. Commun. 40, 1734 (2004). (http://dx.doi.org/10.1039/b402375g)
• 16a. H. A. Latham-Timmons, A. Wolter, J. S. Roach, R. Giare, M. Leuck. Nucleosides, Nucleotides Nucleic Acids 22, 1495 (2003). (http://dx.doi.org/10.1081/NCN-120023019)
• 16b. X.-L. Sun, C. L. Stabler, C. S. Cazalis, E. L. Chaikof. Bioconjugate Chem. 17, 52 (2006). (http://dx.doi.org/10.1021/bc0502311)
• 16c. M. Proupin-Perez, R. Cosstick, L. M. Liz-Marzan, V. Salgueirino-Maceira, M. Brust. Nucleosides, Nucleotides Nucleic Acids 24, 1075 (2005). (http://dx.doi.org/10.1081/NCN-200059170)
• 16d. M. N. Yousaf, B. T. Houseman, M. Mrksich. Proc. Natl. Acad. Sci. USA 98, 5992 (2001). (http://dx.doi.org/10.1073/pnas.101112898)
• 16e. W. S. Dillmore, M. N. Yousaf, M. Mrksich. Langmuir 20, 7223 (2004). (http://dx.doi.org/10.1021/la049826v)
• 16f. F. Rusmini, Z. Zhong, J. Feijen. Biomacromolecules 3, 1775 (2007). (http://dx.doi.org/10.1021/bm061197b)
• 17a. B. Seelig, A. Jaschke. Tetrahedron Lett. 38, 7729 (1997). (http://dx.doi.org/10.1016/S0040-4039(97)10151-4)
• 17b. D. Graham, A. Enright. Curr. Org. Synth. 3, 9 (2006). (http://dx.doi.org/10.2174/157017906775473920)
• 17c. V. Pozsgay, N. E. Vieira, A. Yergey. Org. Lett. 4, 3191 (2002). (http://dx.doi.org/10.1021/ol026179v)
• 17d. R. J. B. H. N. Van den Berg, D. Noort, E. S. Milder-Enacache, G. A. Van der Marel, J. H. Van Boom, H. P. Benschop. Eur. J. Org. Chem. 2593 (1999). (http://dx.doi.org/10.1002/(SICI)1099-0690(199910)1999:10<2593::AID-EJOC2593>3.0.CO;2-C)
• 17e. C. C. A. M. Peeters, P. R. Lagerman, O. de Weers, L. A. Oomen, P. Hoogerhout, M. Beurret, J. T. Poolman. In Vaccine Protocols, A. Robinson, G. Farrar, C. Wiblin (Eds.), p. 111, Humana Press, Totowa, NJ (1996).
• 17f. Methods in Enzymology, Vol. 242, Academic Press, San Diego (1994).
• 17g. In Neoglycoconjugates. Preparation and Applications, Y. C. Lee, R. T. Lee (Eds.), p. 325, Academic Press, New York (1994).
• 17h. J. B. Robbins, R. Schneerson, P. Anderson, D. H. Smith. J. Am. Med. Assoc. 276, 1181 (1996). (http://dx.doi.org/10.1001/jama.276.14.1181)
• 18a. B. Seelig, A. Jaschke. Chem. Biol. 6, 167 (1999). (http://dx.doi.org/10.1016/S1074-5521(99)89008-5)
• 18b. G. M. Husar, D. J. Anziano, M. Leuck, D. P. Sebesta. Nucleosides, Nucleotides Nucleic Acids 20, 559 (2001). (http://dx.doi.org/10.1081/NCN-100002332)
• 19a. J. L. Segura, N. Martin. Chem. Rev. 11, 3199 (1999). (http://dx.doi.org/10.1021/cr990011e)
• 19b. N. Martin, C. Seoane, M. Hanack. Org. Prep. Proc. Int. 23, 237 (1991). (http://dx.doi.org/10.1080/00304949109458320)
• 19c. W. Oppolzer. Synthesis 793 (1978). (http://dx.doi.org/10.1055/s-1978-24895)
• 20a. Y. Wang, W. Song, W. J. Hu, Q. Lin. Angew. Chem., Int. Ed. 48, 5330 (2009). (http://dx.doi.org/10.1002/anie.200901220)
• 20b. W. Song, Y. Wang, J. Qu, M. M. Madden, Q. Lin. Angew. Chem., Int. Ed. 47, 2832 (2008). (http://dx.doi.org/10.1002/anie.200705805)
• 21a. C. A. De Forest, B. D. Polizzotti, K. S. Anseth. Nat. Mater. 8, 659 (2009). (http://dx.doi.org/10.1038/nmat2473)
• 21b. M. Fiore, A. Marra, A. Dondoni. J. Org. Chem. 74, 4422 (2009). (http://dx.doi.org/10.1021/jo900514w)
• 21c. M. Fiore, A. Chambery, A. Marra, A. Dondoni. Org. Biomol. Chem. 7, 3910 (2009). (http://dx.doi.org/10.1039/b912686d)
• 21d. K. L. Killops, L. M. Campos, C. J. Hawker. J. Am. Chem. Soc. 130, 5062 (2008). (http://dx.doi.org/10.1021/ja8006325)
• 21e. L. M. Campos, K. L. Killops, R. Sakai, J. M. J. Paulusse, D. Damiron, E. Drockenmuller, B. W. Messmore, C. J. Hawker. Macromolecules 41, 7063 (2008). (http://dx.doi.org/10.1021/ma801630n)
• 21f. J. W. Chan, B. Yu, C. E. Hoyle, A. B. Lowe. Chem. Commun. 4959 (2008). (http://dx.doi.org/10.1039/b813438c)
• 22. R. M. Hensarling, V. A. Doughty, J. W. Chan, D. L. Patton. J. Am. Chem. Soc. 131, 14673 (2009). (http://dx.doi.org/10.1021/ja9071157)
• 23a. A. Poloukhtine, V. V. Popik. J. Org. Chem. 68, 7833 (2003). (http://dx.doi.org/10.1021/jo034869m)
• 23b. N. K. Urdabayev, A. Poloukhtine, V. V. Popik. Chem. Comm. 454 (2006). (http://dx.doi.org/10.1039/b513248g)
• 23c. A. Poloukhtine, V. V. Popik. J. Phys. Chem. A 110, 1749 (2006). (http://dx.doi.org/10.1021/jp0563641)
• 24a. S. E. Rokita (Ed.). Quinone Methides, Wiley Series of Reactive Intermediates in Chemistry and Biology, Vol. 1, John Wiley, Hoboken (2009).
• 24b. P. Wan, D. W. Brousmiche, C. Z. Chen, J. Cole, M. Lukeman, M. Xu. Pure Appl. Chem. 73, 529 (2001). (http://dx.doi.org/10.1351/pac200173030529)
• 24c. E. A. Leo, J. Delgado, L. R. Domingo, A. Espinos, M. A. Miranda, R. Tormos. J. Org. Chem. 68, 9647 (2003). (http://dx.doi.org/10.1021/jo034918v)
• 24d. Y. Chiang, A. J. Kresge, Y. Zhu. J. Am. Chem. Soc. 122, 9854 (2000). (http://dx.doi.org/10.1021/ja001557h)
• 25. S. Arumugam, V. V. Popik. J. Am. Chem. Soc. 131, 11892 (2009). (http://dx.doi.org/10.1021/ja9031924)
• 26a. A. A. Poloukhtine, N. E. Mbua, M. A. Wolfert, G.-J. Boons, V. V. Popik. J. Am. Chem. Soc. 131, 15769 (2009). (http://dx.doi.org/10.1021/ja9054096)
• 26b. S. V. Orski, A. A. Poloukhtine, S. Arumugam, L. Mao, V. V. Popik, J. Locklin. J. Am. Chem. Soc. 132, 11024 (2010). (http://dx.doi.org/10.1021/ja105066t)
• 26c. C. D. McNitt, V. V. Popik. Org. Biomol. Chem. 10, 8200 (2012). (http://dx.doi.org/10.1039/c2ob26581h)
• 27a. S. Arumugam, V. V. Popik. J. Am. Chem. Soc. 133, 5573 (2011). (http://dx.doi.org/10.1021/ja200356f)
• 27b. S. Arumugam, V. V. Popik. J. Am. Chem. Soc. 133, 15730 (2011). (http://dx.doi.org/10.1021/ja205652m)
• 27c. S. Arumugam, S. Orski, J. Locklin, V. V. Popik. J. Am. Chem. Soc. 134, 179 (2012). (http://dx.doi.org/10.1021/ja210350d)
• 28a. S. Arumugam, V. V. Popik. J. Am. Chem. Soc. 134, 8408 (2012). (http://dx.doi.org/10.1021/ja302970x)
• 28b. S. Arumugam, J. Guo, N. E. Mbua, E. E. Nekongo, G.-J. Boons, V. V. Popik. Chem. Sci. (2013). Submitted for publication.
• 29a. F. R. Fischer, C. Nuckolls. Angew. Chem., Int. Ed. 49, 7257 (2010); (http://dx.doi.org/10.1002/anie.201003549)
• 29b. F. Starke, M. Walter, H.-J. Pietzsch. ARKIVOC 350 (2010). (http://dx.doi.org/10.3998/ark.5550190.0011.b28)
• 30a. R. W. Van De Water, T. R. R. Pettus. Tetrahedron 58, 5367 (2002). (http://dx.doi.org/10.1016/S0040-4020(02)00496-9)
• 30b. H. Wang, Y. Wang, K.‑L. Han, X.-J. Peng. J. Org. Chem. 70, 4910 (2005). (http://dx.doi.org/10.1021/jo0479213)
• 30c. M. Fischer, Y. Shi, B.-P. Zhao, V. Snieckus, P. Wan. Can. J. Chem. 77, 868 (1999).
• 31. S. Arumugam, V. V. Popik. Photochem. Photobiol. Sci. 11, 518 (2012). (http://dx.doi.org/10.1039/c1pp05317e)
• 32. S. V. Orski, K. H. Fries, G. R. Sheppard, J. Locklin. Langmuir 26, 2136 (2010). (http://dx.doi.org/10.1021/la902553f)