Chemical Science
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series of homo-oligomers were synthesised, and duplex formation
was characterised by NMR titration experiments. When length
complementary oligo-triuorophenols and oligo-phosphine
oxides were combined, an order of magnitude increase in
stability was observed for every base-pair added to the duplex. The
effective molarity for the intramolecular H-bonds responsible for
zipping up the duplex is about 30 mM in toluene and in chloro-
form. The uniform increase in duplex stability with oligomer
length suggests that the backbone structure and geometry is likely
to be compatible with the formation of extended duplexes in
longer oligomers. This two-component backbone is more versa-
tile than previous designs, because it provides an opportunity for
varying the diamine component without the need to resynthesise
complex monomer building blocks. The properties of mixed
sequence oligomers and template-directed synthesis using
dynamic imine chemistry are currently under investigation.
Van, I. Verheggen, C. Hendrix and P. Herdewijn, Angew.
Chem., Int. Ed., 1995, 34, 1338–1339; (e) K.-U. Schoning,
P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy and
A. Eschenmoser, Science, 2000, 290, 1347–1351; (f)
L. Zhang, A. Peritz and E. Meggers, J. Am. Chem. Soc., 2005,
127, 4174–4175; (g) A. B. Gerber and C. J. Leumann, Chem.–
Eur. J., 2013, 19, 6990–7006.
6 (a) Z. Chen, P. A. Lichtor, A. P. Berliner, J. C. Chen and D. R. Liu,
Nat. Chem., 2018, 10, 420–427; (b) L. D. Usanov, A. I. Chan,
J. P. Maianti and D. R. Liu, Nat. Chem., 2018, 10, 704–714.
7 (a) A. P. Bisson, F. J. Carver, D. S. Eggleston,
R. C. Haltiwanger, C. A. Hunter, D. L. Livingstone,
J. F. McCabe, C. Rotger and A. E. Rowan, J. Am. Chem. Soc.,
2000, 122, 8856–8868; (b) H. Gong and M. J. Krische, J. Am.
Chem. Soc., 2005, 127, 1719–1725; (c) Y. Yang, Z. Y. Yang,
Y. P. Yi, J. F. Xiang, C. F. Chen, L. J. Wan and Z. G. Shuai,
J. Org. Chem., 2007, 72, 4936–4946.
8 R. Amemiya, N. Saito and M. Yamaguchi, J. Org. Chem., 2008,
73, 7137–7144.
Conflicts of interest
There are no conicts to declare.
9 (a) Y. Tanaka, H. Katagiri, Y. Furusho and E. Yashima,
Angew. Chem., Int. Ed., 2005, 44, 3867–3870; (b) H. Ito,
Y. Furusho, T. Hasegawa and E. Yashima, J. Am. Chem.
Soc., 2008, 130, 14008–14015.
Acknowledgements
L. G. thanks Marie Skłodowska-Curie Actions Individual 10 (a) R. Kramer, J. M. Lehn and A. Marquis-Rigault, Proc. Natl.
Fellowship (H2020-MSCA-IF-2016, DyNAmics – number 745730)
for funding.
Acad. Sci. U. S. A., 1993, 90, 5394–5398; (b) P. N. Taylor and
H. L. Anderson, J. Am. Chem. Soc., 1999, 121, 11538–11545.
11 (a) H. Ito, Y. Furusho, T. Hasegawa and E. Yashima, J. Am.
Chem. Soc., 2008, 130, 14008–14015; (b) A. E. Stross,
Notes and references
˜
`
G. Iadevaia, D. Nunez-Villanueva and C. A. Hunter, J. Am.
1 J. D. Watson and F. H. Crick, Nature, 1953, 171, 964.
Chem. Soc., 2017, 139, 12655–12663.
´
2 (a) C. Tuerk and L. Gold, Science, 1990, 249(4968), 505–510; 12 (a) F. T. Szczypinski and C. A. Hunter, Chem. Sci., 2019, 10,
´
(b) A. D. Ellington and J. W. Szostak, Nature, 1990, 346,
818–822; (c) D. L. Robertson and G. F. Joyce, Nature, 1990,
344, 467–468.
2444–2451; (b) F. T. Szczypinski, L. Gabrielli and
C. A. Hunter, Chem. Sci., 2019, 10, 5397–5404.
13 J. A. Swain, G. Iadevaia and C. A. Hunter, J. Am. Chem. Soc.,
2018, 140(36), 11526–11536.
3 (a) D. H. Appella, Curr. Opin. Chem. Biol., 2009, 13, 687–696;
˜
´
(b) H. Isobe, T. Fujino, N. Yamazaki, M. Guillot-Nieckowski 14 G. Iadevaia, D. Nunez-Villanueva, A. E. Stross and
and E. Nakamura, Org. Lett., 2008, 10, 3729–3732; (c) C. A. Hunter, Org. Biomol. Chem., 2018, 16, 4183.
K. Burgess, R. A. Gibbs, M. L. Metzker and 15 (a) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders
R. Raghavachari, J. Chem. Soc., Chem. Commun., 1994, 915.
4 (a) L. Zhang, Z. Yang, K. Sefah, K. M. Bradley, S. Hoshika,
and J. F. Stoddart, Angew. Chem., Int. Ed., 2002, 41, 898–952;
(b) P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J.-L. Wietor,
J. K. M. Sanders and S. Otto, Chem. Rev., 2006, 106, 3652–
3711; (c) J.-M. Lehn, Chem. Soc. Rev., 2007, 36, 151–160; (d)
J. Li, P. Nowak and S. Otto, J. Am. Chem. Soc., 2013, 135,
9222–9239; (e) M. Mondal and A. K. H. Hirsch, Chem. Soc.
´
M.-J. Kim, H.-J. Kim, G. Zhu, E. Jimenez, S. Cansiz,
I.-T. Teng, C. Champanhac, C. McLendon, C. Liu,
W. Zhang, D. L. Gerloff, Z. Huang, W. Tan and
S. A. Benner, J. Am. Chem. Soc., 2015, 137, 6734–6737; (b)
J. A. Piccirilli, T. Krauch, S. E. Moroney and S. A. Benner,
Nature, 1990, 343, 33–37; (c) B. A. Schweitzer and
E. T. Kool, J. Org. Chem., 1994, 59, 7238–7242; (d) H. Liu,
J. Gao, S. R. Lynch, Y. D. Saito, L. Maynard and E. T. Kool,
˜
´
Rev., 2015, 44, 2455; (f) D. Nunez-Villanueva, M. Ciaccia,
G. Iadevaia, E. Sanna and C. A. Hunter, Chem. Sci., 2019,
˜
´
10, 5258; (g) M. Ciaccia, D. Nunez-Villanueva and
C. A. Hunter, J. Am. Chem. Soc., 2019, 14(127), 10862.
Science, 2003, 302, 868–871; (e) J. C. Delaney, J. Gao, H. Liu, 16 C. A. Hunter, Angew. Chem., Int. Ed., 2004, 43, 5310–5324.
´˜
´
´
N. Shrivastav, J. M. Essigmann and E. T. Kool, Angew. 17 L. Gonzalez-Bulnes, I. Ibanez, L. M. Bedoya, M. Beltran,
´
´
Chem., Int. Ed., 2009, 48, 4524–4527.
S. Catalan, J. Alcamı, S. Fustero and J. Gallego, Angew.
5 (a) A. Eschenmoser, Origins Life Evol. Biospheres, 1997, 27,
Chem., Int. Ed., 2013, 52, 13405–13409.
535–553; (b) S. Obika, D. Nanbu, Y. Hari, K.-i. Morio, Y. In, 18 A. E. Stross, G. Iadevaia and C. A. Hunter, Chem. Sci., 2016, 7,
T. Ishida and T. Imanishi, Tetrahedron Lett., 1997, 38, 94–101.
8735–8738; (c) A. A. Koshkin, S. K. Singh, P. Nielsen, 19 (a) G. Iadevaia, A. E. Stross, A. Neumann and C. A. Hunter,
V. K. Rajwanshi, R. Kumar, M. Meldgaard, C. E. Olsen and
J. Wengel, Tetrahedron, 1998, 54, 3607–3630; (d) A. Aerschot
Chem. Sci., 2016, 7, 1760; (b) A. E. Stross, G. Iadevaia and
C. A. Hunter, Chem. Sci., 2016, 7, 5686.
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