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Articles

Cationic acyclic cucurbit[n]uril-type containers: synthesis and molecular recognition toward nucleotides

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Pages 825-834 | Received 19 Feb 2016, Accepted 13 Mar 2016, Published online: 13 Apr 2016

References

  • Cram, D.J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009–1020; Lehn, J.-M. Angew. Chem. Int. Ed. Engl. 1988, 27, 89–112; Pedersen, C.J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1021–1027; Gutsche, C.D. Acc. Chem. Res. 1983, 16, 161–170; Rebek, J. Acc. Chem. Res. 2009, 42, 1660–1668; Pluth, M.D.; Raymond, K.N. Chem. Soc. Rev. 2007, 36, 161–171; Yoshizawa, M.; Klosterman, J.; Fujita, M. Angew. Chem. Int. Ed. 2009, 48, 3418–3438; Kumari, H.; Deakyne, C.A.; Atwood, J.L. Acc. Chem. Res. 2014, 47, 3080–3088; Kay, E.R.; Leigh, D.A. Angew. Chem. Int. Ed. 2015, 54, 10080–10088.
  • Diederich, F. Angew. Chem. Int. Ed. Engl. 1988, 27, 362–386; Boehmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713–745; Rekharsky, M.V.; Inoue, Y. Chem. Rev. 1998, 98, 1875–1917; Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.-A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022–5023; Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Acc. Chem. Res. 2012, 45, 1294–1308. 10.1002/(ISSN)1521-3773
  • You, L.; Zha, D.; Anslyn, E.V. Chem. Rev. 2015, 115, 7840–7892.10.1021/cr5005524
  • Ma, X.; Zhao, Y. Chem. Rev. 2015, 115, 7794–7839.10.1021/cr500392w
  • Harada, A.; Takashima, Y.; Nakahata, M. Acc. Chem. Res. 2014, 47, 2128–2140.10.1021/ar500109h
  • Garcia-Simon, C.; Gramage-Doria, R.; Raoufmoghaddam, S.; Parella, T.; Costas, M.; Ribas, X.; Reek Joost, N.H. J. Am. Chem. Soc. 2015, 137, 2680–2687; Ramamurthy, V. Acc. Chem. Res. 2015, 48, 2904–2917.10.1021/ja512637k
  • Warmuth, R. Angew. Chem. Int. Ed. 1997, 36, 1347–1350; Mal, P.; Breiner, B.; Rissanen, K.; Nitschke, J.R. Science 2009, 324, 1697–1699; Cram, D.J.; Tanner, M.E.; Thomas, R. Angew. Chem. Int. Ed. 1991, 30, 1024–1027.10.1002/(ISSN)1521-3773
  • Cummings, C.G.; Hamilton, A.D. Curr. Opin. Chem. Biol. 2010, 14, 341–346.10.1016/j.cbpa.2010.04.001
  • Gassensmith, J.J.; Baumes, J.M.; Smith, B.D. Chem. Commun. 2009, 6329–6338.10.1039/b911064j
  • Lee, J.W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621–630; Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem. Int. Ed. 2005, 44, 4844–4870; Nau, W.M.; Florea, M.; Assaf, K.I. Isr. J. Chem. 2011, 51, 559–577; Assaf, K.I.; Nau, W.M. Chem. Soc. Rev. 2015, 44, 394–418; Masson, E.; Ling, X.; Joseph, R.; Kyeremeh-Mensah, L.; Lu, X. RSC Adv. 2012, 2, 1213–1247.10.1021/ar020254k
  • Barrow, S.J.; Kasera, S.; Rowland, M.J.; del Barrio, J.; Scherman, O.A. Chem. Rev. 2015, 115, 12320–12406.10.1021/acs.chemrev.5b00341
  • Freeman, W.A.; Mock, W.L.; Shih, N.-Y. J. Am. Chem. Soc. 1981, 103, 7367–7368; Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540–541; Day, A.I.; Arnold, A.P.; Blanch, R.J.; Snushall, B. J. Org. Chem. 2001, 66, 8094–8100; Day, A.I.; Blanch, R.J.; Arnold, A.P.; Lorenzo, S.; Lewis, G.R.; Dance, I. Angew. Chem. Int. Ed. 2002, 41, 275–277; Liu, S.; Zavalij, P.Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798–16799; Cheng, X.-J.; Liang, L.-L.; Chen, K.; Ji, N.-N.; Xiao, X.; Zhang, J.-X.; Zhang, Y.-Q.; Xue, S.-F.; Zhu, Q.-J.; Ni, X.-L.; Tao, Z. Angew. Chem. Int. Ed. 2013, 52, 7252–7255.10.1021/ja00414a070
  • Mock, W.L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440–4446; Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P.Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959–15967; Rekharsky, M.V.; Mori, T.; Yang, C.; Ko, Y.H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A.E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M.K.; Kim, K.; Inoue, Y. Proc. Nat. Acad. Sci. U.S.A. 2007, 104, 20737–20742; Cao, L.; Šekutor, M.; Zavalij, P.Y.; Mlinaric′-Majerski, K.; Glaser, R.; Isaacs, L. Angew. Chem. Int. Ed. 2014, 53, 988–993; Biedermann, F.; Uzunova, V.D.; Scherman, O.A.; Nau, W.M.; De Simone, A. J. Am. Chem. Soc. 2012, 134, 15318–15323; Moghaddam, S.; Yang, C.; Rekharsky, M.; Ko, Y.H.; Kim, K.; Inoue, Y.; Gilson, M.K. J. Am. Chem. Soc. 2011, 133, 3570–3581.10.1021/jo00373a018
  • Shetty, D.; Khedkar, J.K.; Park, K.M.; Kim, K. Chem. Soc. Rev. 2015, 44, 8747–8761.10.1039/C5CS00631G
  • Isaacs, L. Acc. Chem. Res. 2014, 47, 2052–2062; Del Barrio, J.; Horton, P.; Lairez, D.; Lloyd, G.; Toprakcioglu, C.; Scherman, O. J. Am. Chem. Soc. 2013, 135, 11760–11763; Ko, Y.H.; Kim, E.; Hwang, I.; Kim, K. Chem. Commun. 2007, 1305–1315; Loh, X.J.; del Barrio, J.; Toh, P.P.C.; Lee, T.-C.; Jiao, D.; Rauwald, U.; Appel, E.A.; Scherman, O.A. Biomacromolecules 2012, 13, 84–91.10.1021/ar500075g
  • Vazquez, J.; Remon, P.; Dsouza, R.N.; Lazar, A.I.; Arteaga, J.F.; Nau, W.M.; Pischel, U. Chem. Eur. J. 2014, 20, 9897–9901; Walker, S.; Oun, R.; McInnes, F.J.; Wheate, N.J. Isr. J. Chem. 2011, 51, 616–624; Dong, N.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.; Zhao, Y.; Yang, L.-X. Supramol. Chem. 2008, 20, 659–665; Macartney, D.H. Isr. J. Chem. 2011, 51, 600–615.10.1002/chem.201403405
  • Dsouza, R.; Hennig, A.; Nau, W. Chem. Eur. J. 2012, 18, 3444–3459; Ghale, G.; Lanctot, A.G.; Kreissl, H.T.; Jacob, M.H.; Weingart, H.; Winterhalter, M.; Nau, W.M. Angew. Chem. Int. Ed. 2014, 53, 2762–2765; Norouzy, A.; Azizi, Z.; Nau, W.M. Angew. Chem. Int. Ed. 2015, 54, 792–795.10.1002/chem.201103364
  • Dang, D.; Nguyen, H.; Merkx, M.; Brunsveld, L. Angew. Chem. Int. Ed. 2013, 52, 2915–2919; Lee, H.H.; Choi, T.S.; Lee, S.J.C.; Lee, J.W.; Park, J.; Ko, Y.H.; Kim, W.J.; Kim, K.; Kim, H.I. Angew. Chem. Int. Ed. 2014, 53, 7461–7465; Chinai, J.M.; Taylor, A.B.; Ryno, L.M.; Hargreaves, N.D.; Morris, C.A.; Hart, P.J.; Urbach, A.R. J. Am. Chem. Soc. 2011, 133, 8810–8813; Urbach, A.R.; Ramalingam, V. Isr. J. Chem. 2011, 51, 664–678; Smith, L.C.; Leach, D.G.; Blaylock, B.E.; Ali, O.A.; Urbach, A.R. J. Am. Chem. Soc. 2015, 137, 3663–3669; Rekharsky, M.V.; Yamamura, H.; Ko, Y.H.; Selvapalam, N.; Kim, K.; Inoue, Y. Chem. Commun. 2008, 2236–2238.10.1002/anie.201208239
  • Appel, E.; del Barrio, J.; Loh, X.; Scherman, O. Chem. Soc. Rev. 2012, 41, 6195–6214.10.1039/c2cs35264h
  • Lim, S.; Kim, H.; Selvapalam, N.; Kim, K.-J.; Cho, S.J.; Seo, G.; Kim, K. Angew. Chem. Int. Ed. 2008, 47, 3352–3355; Miyahara, Y.; Abe, K.; Inazu, T. Angew. Chem. Int. Ed. 2002, 41, 3020–3023; Tian, J.-A.; Ma, S.-Q.; Thallapally, P.K.; Fowler, D.; McGrail, B.P.; Atwood, J.L. Chem. Commun. 2011, 47, 7626–7628.10.1002/(ISSN)1521-3773
  • Jon, S.Y.; Selvapalam, N.; Oh, D.H.; Kang, J.-K.; Kim, S.-Y.; Jeon, Y.J.; Lee, J.W.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186–10187; Kim, E.; Kim, D.; Jung, H.; Lee, J.; Paul, S.; Selvapalam, N.; Yang, Y.; Lim, N.; Park, C.G.; Kim, K. Angew. Chem. Int. Ed. 2010, 49, 4405–4408; Jung, H.; Park, K.M.; Yang, J.-A.; Oh, E.J.; Lee, D.-W.; Park, K.; Ryu, S.H.; Hahn, S.K.; Kim, K. Biomaterials 2011, 32, 7687–7694; Lee, D.-W.; Park, K.; Banerjee, M.; Ha, S.; Lee, T.; Suh, K.; Paul, S.; Jung, H.; Kim, J.; Selvapalam, N.; Ryu, S.; Kim, K. Nat. Chem. 2011, 3, 154–159; Jung, H.; Park, J.S.; Yeom, J.; Selvapalam, N.; Park, K.M.; Oh, K.; Yang, J.-A.; Park, K.H.; Hahn, S.K.; Kim, K. Biomacromolecules 2014, 15, 707–714; Jang, M.; Kim, H.; Lee, S.; Kim, H.W.; Khedkar, J.K.; Rhee, Y.M.; Hwang, I.; Kim, K.; Oh, J.H. Adv. Funct. Mater. 2015, 25, 4882–4888; Yeom, J.; Kim, S.J.; Jung, H.; Namkoong, H.; Yang, J.; Hwang, B.W.; Oh, K.; Kim, K.; Sung, Y.C.; Hahn, S.K. Adv. Healthcare Mater. 2015, 4, 237–244.10.1021/ja036536c
  • Lucas, D.; Minami, T.; Iannuzzi, G.; Cao, L.; Wittenberg, J.B.; Anzenbacher, P.; Isaacs, L. J. Am. Chem. Soc. 2011, 133, 17966–17976; Cao, L.; Isaacs, L. Org. Lett. 2012, 14, 3072–3075; Vinciguerra, B.; Cao, L.; Cannon, J.R.; Zavalij, P.Y.; Fenselau, C.; Isaacs, L. J. Am. Chem. Soc. 2012, 134, 13133–13140; Cao, L.; Hettiarachchi, G.; Briken, V.; Isaacs, L. Angew. Chem. Int. Ed. 2013, 52, 12033–12037.10.1021/ja208229d
  • Zhao, N.; Lloyd, G.; Scherman, O. Chem. Commun. 2012, 48, 3070–3072; Ahn, Y.; Jang, Y.; Selvapalam, N.; Yun, G.; Kim, K. Angew. Chem. Int. Ed. 2013, 52, 3140–3144; Ayhan, M.M.; Karoui, H.; Hardy, M.; Rockenbauer, A.; Charles, L.; Rosas, R.; Udachin, K.; Tordo, P.; Bardelang, D.; Ouari, O. J. Am. Chem. Soc. 2015, 137, 10238–10245.10.1039/c2cc17433b
  • Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J.B.; Zavalij, P.Y.; Briken, V.; Isaacs, L. Nat. Chem. 2012, 4, 503–510; Ma, D.; Zhang, B.; Hoffmann, U.; Sundrup, M.G.; Eikermann, M.; Isaacs, L. Angew. Chem. Int. Ed. 2012, 51, 11358–11362; Shen, C.; Ma, D.; Meany, B.; Isaacs, L.; Wang, Y. J. Am. Chem. Soc. 2012, 134, 7254–7257; Gilberg, L.; Zhang, B.; Zavalij, P.Y.; Sindelar, V.; Isaacs, L. Org. Biomol. Chem. 2015, 13, 4041–4050.10.1038/nchem.1326
  • Zhang, B.; Isaacs, L. J. Med. Chem. 2014, 57, 9554–9563.10.1021/jm501276u
  • Zhang, B.; Zavalij, P.Y.; Isaacs, L. Org. Biomol. Chem. 2014, 12, 2413–2422.10.1039/C3OB42603C
  • Stancl, M.; Necas, M.; Taraba, J.; Sindelar, V. J. Org. Chem. 2008, 73, 4671–4675; Stancl, M.; Hodan, M.; Sindelar, V. Org. Lett. 2009, 11, 4184–4187; Stancl, M.; Gargulakova, Z.; Sindelar, V. J. Org. Chem. 2012, 77, 10945–10948; Stancl, M.; Gilberg, L.; Ustrnul, L.; Necas, M.; Sindelar, V. Supramol. Chem. 2014, 26, 168–172.10.1021/jo800699s
  • Sigwalt, D.; Ahlbrand, S.; Zhang, M.; Vinciguerra, B.; Briken, V.; Isaacs, L. Org. Lett. 2015, 5914–5917.10.1021/acs.orglett.5b03145
  • Kuchelmeister, H.Y.; Schmuck, C. Chem. Eur. J. 2011, 17, 5311–5318; Inclan, M.; Albelda, M.T.; Carbonell, E.; Blasco, S.; Bauza, A.; Frontera, A.; Garcia-Espana, E. Chem. Eur. J. 2014, 20, 3730–3741; Hosseini, M.W.; Blacker, A.J.; Lehn, J.-M. J. Am. Chem. Soc. 1990, 112, 3896–3904; Guo, Y.-H.; Ge, Q.-C.; Lin, H.; Lin, H.-K.; Zhu, S.-R. Polyhedron 2002, 21, 1005–1015; Delepine, A.-S.; Tripier, R.; Baccon, M.L.; Handel, H. Eur. J. Org. Chem. 2010, 5380–5390; Moreno-Corral, R.; Lara, K.O. Supramol. Chem. 2008, 20, 427–435; Bazzicalupi, C.; Bencini, A.; Biagini, S.; Faggi, E.; Meini, S.; Giorgi, C.; Spepi, A.; Valtancoli, B. J. Org. Chem. 2009, 74, 7349–7363; Arranz-Mascaros, P.; Bazzicalupi, C.; Bianchi, A.; Giorgi, C.; Goldino-Salido, M.L.; Gutierrez-Valero, M.D.; Lopez-Garzon, R.; Valtancoli, B. New J. Chem. 2011, 35, 1883–1891; Abe, H.; Mawatari, Y.; Teraoka, H.; Fujimoto, K.; Inouye, M. J. Org. Chem. 2004, 69, 495–504; Bencini, A.; Biagini, S.; Giorgi, C.; Handel, H.; Baccon, M.L.; Mariani, P.; Paoletti, P.; Paoli, P.; Rossi, P.; Tripier, R.; Valtancoli, B. Eur. J. Org. Chem. 2009, 5610–5621.10.1002/chem.v17.19
  • Svec, J.; Necas, M.; Sindelar, V. Angew. Chem. Int. Ed. 2010, 49, 2378–2381; Svec, J.; Dusek, M.; Fejfarova, K.; Stacko, P.; Klan, P.; Kaifer, A.E.; Li, W.; Hudeckova, E.; Sindelar, V. Chem. Eur. J. 2011, 17, 5605–5612; Havel, V.; Sindelar, V.; Necas, M.; Kaifer, A.E. Chem. Commun. 2014, 50, 1372–1374; Yawer, M.A.; Havel, V.; Sindelar, V. Angew. Chem. Int. Ed. 2015, 54, 276–279; Prigorchenko, E.; Oeren, M.; Kaabel, S.; Fomitsenko, M.; Reile, I.; Jarving, I.; Tamm, T.; Topic, F.; Rissanen, K.; Aav, R. Chem. Commun. 2015, 51, 10921–10924; Lisbjerg, M.; Jessen, B.M.; Rasmussen, B.; Nielsen, B.E.; Madsen, A.O.; Pittelkow, M. Chem. Sci. 2014, 5, 2647–2650; Lisbjerg, M.; Valkenier, H.; Jessen, B.M.; Al-Kerdi, H.; Davis, A.P.; Pittelkow, M. J. Am. Chem. Soc. 2015, 137, 4948–4951; Singh, M.; Solel, E.; Keinan, E.; Reany, O. Chem. Eur. J. 2015, 21, 536–540; Parvari, G.; Annamalai, S.; Borovoi, I.; Chechik, H.; Botoshansky, M.; Pappo, D.; Keinan, E. Chem. Commun. 2014, 50, 2494–2497.10.1002/anie.201000420
  • Ma, D.; Zavalij, P.Y.; Isaacs, L. J. Org. Chem. 2010, 75, 4786–4795.10.1021/jo100760g
  • Holliday, B.J.; Jeon, Y.-M.; Mirkin, C.A.; Stern, C.L.; Incarvito, C.D.; Zakharov, L.N.; Sommer, R.D.; Rheingold, A.L. Organomettalics 2002, 21, 5713–5725.10.1021/om020739c

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