High-Affinity Hybridization of Complementary Aromatic Oligoamide Strands in Water.
Aromatic Oligoamide
Artificial Hybridization
Double Helix
Foldamer
Self-Assembly
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
27 Nov 2023
27 Nov 2023
Historique:
received:
10
08
2023
medline:
7
10
2023
pubmed:
7
10
2023
entrez:
7
10
2023
Statut:
ppublish
Résumé
We prepared a series of water-soluble aromatic oligoamide sequences all composed of a segment prone to form a single helix and a segment prone to dimerize into a double helix. These sequences exclusively assemble as antiparallel duplexes. The modification of the duplex inner rim by varying the nature of the substituents borne by the aromatic monomers allowed us to identify sequences that can hybridize by combining two chemically different strands, with high affinity and complete selectivity in water. X-ray crystallography confirmed the expected antiparallel configuration of the duplexes whereas NMR spectroscopy and mass spectrometry allowed us to assess precisely the extent of the hybridization. The hybridization kinetics of the aromatic strands was shown to depend on both the nature of the substituents responsible for strand complementarity and the length of the aromatic strand. These results highlight the great potential of aromatic hetero-duplex as a tool to construct non-symmetrical dynamic supramolecular assemblies.
Identifiants
pubmed: 37804233
doi: 10.1002/anie.202311639
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202311639Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
J.-M. Lehn, Science 2002, 295, 2400;
M. M. Safont-Sempere, G. Fernández, F. Würthner, Chem. Rev. 2011, 111, 5784.
J. D. Watson, F. H. Crick, Nature 1953, 171, 737;
B. A. Wallace, K. Ravikumar, Science 1988, 241, 182;
D. N. Woolfson, Adv. Protein Chem. 2005, 70, 79.
B. Gong, Acc. Chem. Res. 2012, 45, 2077;
A. E. Stross, G. Iadevaia, C. A. Hunter, Chem. Sci. 2016, 7, 94;
D. Núñez-Villanueva, C. A. Hunter, Chem. Sci. 2017, 8, 206;
A. E. Stross, G. Iadevaia, G. D. Núñez-Villanueva, C. A. Hunter, J. Am. Chem. Soc. 2017, 139, 12655;
P. Troselj, P. Bolgar, P. Ballester, C. A. Hunter, J. Am. Chem. Soc. 2021, 143, 8669;
E. A. Archer, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 5074;
E. A. Archer, N. T. Goldberg, V. Lynch, M. J. Krische, J. Am. Chem. Soc. 2000, 122, 5006.
E. Yashima, N. Ousaka, D. Taura, K. Shimomura, T. Ikai, K. Maeda, Chem. Rev. 2016, 116, 13752;
D. Haldar, C. Schmuck, Chem. Soc. Rev. 2009, 38, 363;
J. Li, J. A. Wisner, M. C. Jennings, Org. Lett. 2007, 9, 3267;
H. Goto, H. Katagiri, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2006, 128, 7176;
H. Sugiura, R. Amemiya, M. Yamaguchi, Chem. Asian J. 2008, 3, 244;
C. J. Massena, D. A. Decato, O. B. Berryman, Angew. Chem. Int. Ed. 2018, 57, 16109;
Y. Liu, F. C. Parks, W. Zhao, A. H. Flood, J. Am. Chem. Soc. 2018, 140, 15477;
F. C. Parks, Y. Liu, S. Debnath, S. R. Stutsman, K. Raghavachari, A. H. Flood, J. Am. Chem. Soc. 2018, 140, 17711;
R. Kramer, J.-M. Lehn, A. Marquis-Rigault, Proc. Natl. Acad. Sci. USA 1993, 90, 5394.
C. Zhan, J.-M. Léger, I. Huc, Angew. Chem. Int. Ed. 2006, 45, 4625;
Q. Gan, F. Li, G. Li, B. Kauffmann, J. Xiang, I. Huc, H. Jiang Chem. Commun. 2010, 46, 297;
M. L. Singleton, G. Pirotte, B. Kauffmann, Y. Ferrand, I. Huc, Angew. Chem. Int. Ed. 2014, 53, 13140;
V. C. M. Smith, J.-M. Lehn, Chem. Commun. 1996, 2733.
Y. Tanaka, H. Hatagiri, Y. Furusho, E. Yashima, Angew. Chem. Int. Ed. 2005, 44, 3867;
H. Ito, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2008, 130, 14008;
H. Yamada, Z. Q. Wu, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2012, 134, 9506.
M. Thiele, F. Octa-Smolin, S. Thölke, C. Wölper, J. Linders, C. Mayer, G. Haberhauer, J. Niemeyer, Chem. Commun. 2021, 57, 9842.
V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J. M. Lehn, Nature 2000, 407, 720;
Q. Gan, C. Bao, B. Kauffmann, A. Grélard, J. Xiang, S. Liu, I. Huc, H. Jiang, Angew. Chem. Int. Ed. 2008, 47, 1715;
Q. Gan, X. Wang, B. Kauffmann, F. Rosu, Y. Ferrand, I. Huc, Nat. Nanotechnol. 2017, 12, 447.
J. Shang, Q. Gan, S. J. Dawson, F. Rosu, H. Jiang, Y. Ferrand, I. Huc, Org. Lett. 2014, 16, 4992.
V. Corvaglia, F. Sanchez, F. S. Menke, C. Douat, I. Huc, Chem. Eur. J. 2023, 29, 202300898.
Deposition numbers 2216832 ((5)2) and 2232111 ((6)2) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Y. Ferrand, N. Chandramouli, A. M. Kendhale, C. Aube, B. Kauffmann, A. Grélard, M. Laguerre, D. Dubreuil, I. Huc, J. Am. Chem. Soc. 2012, 134, 11282.
Zerbetto, Venturini, J. Am. Chem. Soc. 2004, 126, 2362;
J. Phys. Chem. B 2017, 121, 10064.