10.1002/anie.202001369
Angewandte Chemie International Edition
COMMUNICATION
[10]
[11]
a) J. Brinkmann, D. Wasserberg, P. Jonkheijm, Eur.
Polym. J. 2016, 83, 380-389; b) J. M. Chinai, A. B. Taylor,
L. M. Ryno, N. D. Hargreaves, C. A. Morris, P. J. Hart, A.
R. Urbach, J. Am. Chem. Soc. 2011, 133, 8810-8813; c)
A. R. Urbach, V. Ramalingam, Isr. J. Chem. 2011, 51,
664-678.
a) W. L. Mock, T. A. Irra, J. P. Wepsiec, T. L. Manimaran,
J. Org. Chem. 1983, 48, 3619-3620; b) T. C. Krasia, J. H.
G. Steinke, Chem. Commun. 2002, 22-23.
dynamic biological processes. We are currently looking into
enhancing solvent and buffer tolerance to enable these
applications in living systems. Lastly, the here presented work can
be adopted to different biocompatible metal carbene catalysts
such as NHC-Pd[29] and NHC-Ru[30] in order to regulate their
catalytic activity.[31]
[12]
[13]
C. Klöck, R. N. Dsouza, W. M. Nau, Org. Lett. 2009, 11,
2595-2598.
G. Y. Tonga, Y. Jeong, B. Duncan, T. Mizuhara, R. Mout,
R. Das, S. T. Kim, Y.-C. Yeh, B. Yan, S. Hou, V. M.
Rotello, Nat. Chem. 2015, 7, 597.
a) V. Blanco, A. Carlone, K. D. Hänni, D. A. Leigh, B.
Lewandowski, Angew. Chem. Int. Ed. 2012, 51, 5166-
5169; b) V. Blanco, D. A. Leigh, U. Lewandowska, B.
Lewandowski, V. Marcos, J. Am. Chem. Soc. 2014, 136,
15775-15780; c) V. Blanco, D. A. Leigh, V. Marcos, J. A.
Morales-Serna, A. L. Nussbaumer, J. Am. Chem. Soc.
2014, 136, 4905-4908.
Acknowledgements
Generous funding by the European Research Council (ERC,
consolidator grant 726381 (RE), starting grant 639005 (SvK)) and
the Reumafonds Fundamental Research Grant (15-2-202, SvK)
is acknowledged. CJ was supported by Vrije Programma (SMPS)
of the Foundation for Fundamental Research on Matter. Dr. S. J.
Eustace is acknowledged for helping with NMR experiments.
[14]
[15]
[16]
[17]
a) P. Michael, M. Biewend, W. H. Binder, Macromol. Rapid
Commun. 2018, 39, 1800376; b) P. Michael, W. H. Binder,
Angew. Chem. Int. Ed. 2015, 54, 13918-13922.
V. Hong, A. K. Udit, R. A. Evans, M. G. Finn,
Chembiochem : a European journal of chemical biology
2008, 9, 1481-1486.
a) M. A. Tasdelen, Y. Yagci, Angew. Chem. Int. Ed. 2013,
52, 5930-5938; b) R. S. Stoll, S. Hecht, Angew. Chem. Int.
Ed. 2010, 49, 5054-5075; c) C. Maity, F. Trausel, R.
Eelkema, Chem. Sci. 2018, 9, 5999-6005.
S. De, S. Pramanik, M. Schmittel, Angew. Chem. Int. Ed.
2014, 53, 14255-14259.
C. Gaulier, A. Hospital, B. Legeret, A. F. Delmas, V.
Aucagne, F. Cisnetti, A. Gautier, Chem. Commun. 2012,
48, 4005-4007.
Keywords: Cucurbit[n]uril • protein labelling • click chemistry •
host-guest chemistry • catalysis
[1]
[2]
[3]
M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-
3015.
V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B.
Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
a) C. J. Pickens, S. N. Johnson, M. M. Pressnall, M. A.
Leon, C. J. Berkland, Bioconj. Chem. 2018, 29, 686-701;
b) L. Liang, D. Astruc, Coord. Chem. Rev. 2011, 255,
2933-2945; c) T. Murakami, H. R. Brown, C. J. Hawker, J.
Polym. Sci., Part A: Polym. Chem. 2016, 54, 1459-1467;
d) A. A. Alzahrani, M. Saed, C. M. Yakacki, H. B. Song, N.
Sowan, J. J. Walston, P. K. Shah, M. K. McBride, J. W.
Stansbury, C. N. Bowman, Polym. Chem. 2018, 9, 121-
130.
[18]
[19]
[20]
[21]
S. I. Presolski, V. Hong, S.-H. Cho, M. G. Finn, J. Am.
Chem. Soc. 2010, 132, 14570-14576.
C. Araman, L. Pieper-Pournara, T. van Leeuwen, A. S. B.
Kampstra, T. Bakkum, M. H. S. Marqvorsen, C. R.
Nascimento, G. J. Mirjam Groenewold, W. van der Wulp,
M. G. M. Camps, H. S. Overkleeft, F. A. Ossendorp, R. E.
M. Toes, S. I. van Kasteren, bioRxiv 2019, 439323.
X. Peng, E. S. Nelson, J. L. Maiers, K. A. DeMali, in Int.
Rev. Cell Mol. Biol., Vol. 287 (Ed.: K. W. Jeon), Academic
Press, 2011, pp. 191-231.
J. van Heemst, D. T. S. L. Jansen, S. Polydorides, A. K.
Moustakas, M. Bax, A. L. Feitsma, D. G. Bontrop-Elferink,
M. Baarse, D. van der Woude, G.-J. Wolbink, T. Rispens,
F. Koning, R. R. P. de Vries, G. K. Papadopoulos, G.
Archontis, T. W. Huizinga, R. E. Toes, Nat. Comm. 2015,
6, 6681.
H. Yang, Y. Liu, L. Yang, K. Liu, Z. Wang, X. Zhang,
Chem. Commun. 2013, 49, 3905-3907.
a) A. E. Kaifer, Chemphyschem 2013, 14, 1107-1108; b)
L. Peng, A. Feng, M. Huo, J. Yuan, Chem. Commun.
2014, 50, 13005-13014.
W. S. Jeon, K. Moon, S. H. Park, H. Chun, Y. H. Ko, J. Y.
Lee, E. S. Lee, S. Samal, N. Selvapalam, M. V.
Rekharsky, V. Sindelar, D. Sobransingh, Y. Inoue, A. E.
Kaifer, K. Kim, J. Am. Chem. Soc. 2005, 127, 12984-
12989.
D. V. Berdnikova, T. M. Aliyeu, T. Paululat, Y. V. Fedorov,
O. A. Fedorova, H. Ihmels, Chem. Commun. 2015, 51,
4906-4909.
[4]
[5]
[6]
a) P. E. Farahani, S. M. Adelmund, J. A. Shadish, C. A.
DeForest, J. Mater. Chem. 2017, 5, 4435-4442; b) C. P.
Ramil, Q. Lin, Curr. Opin. Chem. Biol. 2014, 21, 89-95.
F. Trausel, C. Maity, J. M. Poolman, D. S. J. Kouwenberg,
F. Versluis, J. H. van Esch, R. Eelkema, Nat. Comm.
2017, 8, 879.
a) A. Galán, G. Gil-Ramírez, P. Ballester, Org. Lett. 2013,
15, 4976-4979; b) Y.-C. Horng, P.-S. Huang, C.-C. Hsieh,
C.-H. Kuo, T.-S. Kuo, Chem. Commun. 2012, 48, 8844-
8846; c) N. Nishimura, K. Yoza, K. Kobayashi, J. Am.
Chem. Soc. 2010, 132, 777-790; d) M. L. C. Quan, D. J.
Cram, J. Am. Chem. Soc. 1991, 113, 2754-2755; e) R.
Eelkema, K. Maeda, B. Odell, H. L. Anderson, J. Am.
Chem. Soc. 2007, 129, 12384-12385.
[22]
[23]
[24]
[25]
[7]
[8]
Y. Jin Jeon, S.-Y. Kim, Y. Ho Ko, S. Sakamoto, K.
Yamaguchi, K. Kim, Org. Biomol. Chem. 2005, 3, 2122-
2125.
a) Y. Chen, Z. Huang, H. Zhao, J.-F. Xu, Z. Sun, X.
Zhang, ACS Appl. Mater. & Interfaces 2017, 9, 8602-8608;
b) R. Oun, R. S. Floriano, L. Isaacs, E. G. Rowan, N. J.
Wheate, Toxicol. Res. 2014, 3, 447-455; c) C. P.
Carvalho, V. D. Uzunova, J. P. Da Silva, W. M. Nau, U.
Pischel, Chem. Commun. 2011, 47, 8793-8795; d) S.
Walker, R. Oun, F. J. McInnes, N. J. Wheate, Isr. J. Chem.
2011, 51, 616-624; e) L. Zou, A. S. Braegelman, M. J.
Webber, ACS Cent. Sci. 2019, 5, 1035-1043.
[26]
[27]
[28]
[29]
P. Montes-Navajas, M. González-Béjar, J. C. Scaiano, H.
García, Photoch. Photobio. Sci. 2009, 8, 1743-1747.
D. Cherukaraveedu, P. T. Cowling, G. P. Birch, M.
Bradley, A. Lilienkampf, Org. Biomol. Chem. 2019, 17,
5533-5537.
a) M. Süßner, H. Plenio, Angew. Chem. Int. Ed. 2005, 44,
6885-6888; b) J. Tomasek, J. Schatz, Green Chem. 2013,
15, 2317-2338.
[9]
a) X. Lu, L. Isaacs, Angew. Chem. Int. Ed. 2016, 55, 8076-
8080; b) J. Mohanty, N. Thakur, S. Dutta Choudhury, N.
Barooah, H. Pal, A. C. Bhasikuttan, The Journal of
Physical Chemistry B 2012, 116, 130-135; c) M. Shaikh, J.
Mohanty, A. C. Bhasikuttan, V. D. Uzunova, W. M. Nau, H.
Pal, Chem. Commun. 2008, 3681-3683; d) F. Biedermann,
D. Hathazi, W. M. Nau, Chem. Commun. 2015, 51, 4977-
4980; e) G. Ghale, A. G. Lanctôt, H. T. Kreissl, M. H.
Jacob, H. Weingart, M. Winterhalter, W. M. Nau, Angew.
Chem. Int. Ed. 2014, 53, 2762-2765.
[30]
[31]
E. Peris, Chem. Rev. 2018, 118, 9988-10031.
4
This article is protected by copyright. All rights reserved.