Reversing Chemoselectivity: Simultaneous Positive and Negative Catalysis by Chemically Equivalent Rims of a Cucurbit[7]uril Host
Dr. Nazar Rad
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorDr. Oksana Danylyuk
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorCorresponding Author
Prof. Volodymyr Sashuk
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorDr. Nazar Rad
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorDr. Oksana Danylyuk
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorCorresponding Author
Prof. Volodymyr Sashuk
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Search for more papers by this authorGraphical Abstract
Double action: A cucurbit[7]uril host can promote and inhibit two reactions simultaneously, leading to the diversion of the normal reaction course with the reversal of chemoselectivity. These findings may give insight into the action of enzyme mimics and other chemical networks.
Abstract
Enzyme catalysis has always been an inspiration and an unattainable goal for chemists due to features such as high specificity, selectivity, and efficiency. Here, we disclose a feature neither common in enzymes nor ever described for enzyme mimics, but one that could prove crucial for the catalytic performance of the latter, namely the ability to catalyze and inhibit two different reactions at the same time. Remarkably, this can be realized by two identical, spatially resolved catalytic sites. In the future, such a synchronized catalyst action could be used not only for controlling chemoselectivity, as in the present case, but also for regulating other types of chemical reactivity.
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References
- 1
- 1aL. Pauling, Chem. Eng. News 1946, 24, 1375–1377;
- 1bL. Pauling, Nature 1948, 161, 707.
- 2
- 2aB. Vögeli, T. J. Erb, Curr. Opin. Chem. Biol. 2018, 47, 94–100;
- 2bJ. Rétey, Angew. Chem. Int. Ed. Engl. 1990, 29, 355–361; Angew. Chem. 1990, 102, 373–379.
- 3
- 3aE. Kuah, S. Toh, J. Yee, Q. Ma, Z. Gao, Chem. Eur. J. 2016, 22, 8404–8430;
- 3bM. Raynal, P. Ballester, A. Vidal-Ferran, P. W. N. M. van Leeuwen, Chem. Soc. Rev. 2014, 43, 1734–1787.
- 4
- 4aR. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997–2012;
- 4b“Calixarenes in Organo and Biomimetic Catalysis”: M. Yilmaz, S. Sayin, in Calixarenes and Beyond (Eds.: ), Springer International Publishing, Cham, 2016, pp. 719–742.
10.1007/978-3-319-31867-7_27 Google Scholar
- 5
- 5aC. J. Brown, F. D. Toste, R. G. Bergman, K. N. Raymond, Chem. Rev. 2015, 115, 3012–3035;
- 5bS. Zarra, D. M. Wood, D. A. Roberts, J. R. Nitschke, Chem. Soc. Rev. 2015, 44, 419–432.
- 6
- 6aQ. Zhang, L. Catti, K. Tiefenbacher, Acc. Chem. Res. 2018, 51, 2107–2114;
- 6bY. Zhu, J. Rebek, Jr., Y. Yu, Chem. Commun. 2019, 55, 3573–3577.
- 7
- 7aJ. Wu, X. Wang, Q. Wang, Z. Lou, S. Li, Y. Zhu, L. Qin, H. Wei, Chem. Soc. Rev. 2019, 48, 1004–1076;
- 7bY. Huang, J. Ren, X. Qu, Chem. Rev. 2019, 119, 4357–4412.
- 8
- 8aK. I. Assaf, W. M. Nau, Chem. Soc. Rev. 2015, 44, 394–418;
- 8bB. C. Pemberton, R. Raghunathan, S. Volla, J. Sivaguru, Chem. Eur. J. 2012, 18, 12178–12190;
- 8cL. Zheng, S. Sonzini, M. Ambarwati, E. Rosta, O. A. Scherman, A. Herrmann, Angew. Chem. Int. Ed. 2015, 54, 13007–13011; Angew. Chem. 2015, 127, 13199–13203;
- 8dA. Palma, M. Artelsmair, G. Wu, X. Lu, S. J. Barrow, N. Uddin, E. Rosta, E. Masson, O. A. Scherman, Angew. Chem. Int. Ed. 2017, 56, 15688–15692; Angew. Chem. 2017, 129, 15894–15898.
- 9
- 9aF. Tian, D. Jiao, F. Biedermann, O. A. Scherman, Nat. Commun. 2012, 3, 1207;
- 9bH.-B. Cheng, Y.-M. Zhang, C. Xu, Y. Liu, Sci. Rep. 2014, 4, 4210;
- 9cM. Baroncini, C. Gao, V. Carboni, A. Credi, E. Previtera, M. Semeraro, M. Venturi, S. Silvi, Chem. Eur. J. 2014, 20, 10737–10744;
- 9dJ. Wu, L. Isaacs, Chem. Eur. J. 2009, 15, 11675–11680;
- 9eW. Wang, X. Wang, J. Cao, J. Liu, B. Qi, X. Zhou, S. Zhang, D. Gabel, W. M. Nau, K. I. Assaf, H. Zhang, Chem. Commun. 2018, 54, 2098–2101;
- 9fH. Huang, A. Juan, N. Katsonis, J. Huskens, Tetrahedron 2017, 73, 4913–4917.
- 10H. Mutlu, C. M. Geiselhart, C. Barner-Kowollik, Mater. Horiz. 2018, 5, 162–183.
- 11S. J. Barrow, S. Kasera, M. J. Rowland, J. del Barrio, O. A. Scherman, Chem. Rev. 2015, 115, 12320–12406.
- 12
- 12aV. Sashuk, H. Butkiewicz, M. Fialkowski, O. Danylyuk, Chem. Commun. 2016, 52, 4191–4194;
- 12bC. Klöck, R. N. Dsouza, W. M. Nau, Org. Lett. 2009, 11, 2595–2598.
- 13J. Kalia, R. T. Raines, Angew. Chem. Int. Ed. 2008, 47, 7523–7526; Angew. Chem. 2008, 120, 7633–7636.
- 14
- 14aL. Scorsin, J. A. Roehrs, R. R. Campedelli, G. F. Caramori, A. O. Ortolan, R. L. T. Parreira, H. D. Fiedler, A. Acuña, L. García-Río, F. Nome, ACS Catal. 2018, 8, 12067–12079;
- 14bN. Basilio, L. García-Río, J. A. Moreira, M. Pessêgo, J. Org. Chem. 2010, 75, 848–855;
- 14cW. Gong, J. Ma, Z. Zhao, F. Gao, F. Liang, H. Zhang, S. Liu, J. Org. Chem. 2017, 82, 3298–3301.
- 15D. H. Macartney, Isr. J. Chem. 2018, 58, 230–243.
- 16H. Cong, C.-R. Li, S.-F. Xue, Z. Tao, Q.-J. Zhu, G. Wei, Org. Biomol. Chem. 2011, 9, 1041–1046.
- 17S. Senler, B. Cheng, A. E. Kaifer, Org. Lett. 2014, 16, 5834–5837.
- 18T. Ogoshi, S. Kanai, S. Fujinami, T.-a. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 2008, 130, 5022–5023.
- 19
- 19aS. Kosiorek, B. Rosa, T. Boinski, H. Butkiewicz, M. P. Szymanski, O. Danylyuk, A. Szumna, V. Sashuk, Chem. Commun. 2017, 53, 13320–13323;
- 19bS. Kosiorek, H. Butkiewicz, O. Danylyuk, V. Sashuk, Chem. Commun. 2018, 54, 6316–6319.
- 20M. Szewczyk, G. Sobczak, V. Sashuk, ACS Catal. 2018, 8, 2810–2814.
