Anion Recognition and Induced Self-Assembly of an α,γ-Cyclic Peptide To Form Spherical Clusters
Nuria Rodríguez-Vázquez
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorDr. Manuel Amorín
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorDr. Ignacio Alfonso
Departamento de Química Biológica y Modelización Molecular, Instituto de Química Avanzada de Cataluña (IQAC-CSIC), Jordi Girona, 18–26, 08034 Barcelona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Juan R. Granja
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorNuria Rodríguez-Vázquez
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorDr. Manuel Amorín
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorDr. Ignacio Alfonso
Departamento de Química Biológica y Modelización Molecular, Instituto de Química Avanzada de Cataluña (IQAC-CSIC), Jordi Girona, 18–26, 08034 Barcelona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Juan R. Granja
Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Search for more papers by this authorAbstract
A cyclic octapeptide composed of hydroxy-functionalized γ-amino acids folds in a “V-shaped” conformation that allows the selective recognition of anions such as chloride, nitrate, and carbonate. The process involves the simultaneous self-assembly of six peptide subunits and the recognition of four anions to form a tetrahedral structure, in which the anions are located at the corners of the resulting structure. Each anion is coordinated to three different peptides. The structure was fully characterized by several techniques, including NMR spectroscopy and X-ray diffraction, and the material was able to facilitate the transmembrane transport of chloride ions.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange201511857-sup-0001-misc_information.pdf18.5 MB | Supplementary |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1A. C. Mendes, E. T. Baran, R. L. Reis, H. S. Azevedo, WIREs Nanomed. Nanobiotechnol. 2013, 5, 582–612.
- 2J. W. Steed, Nat. Chem. 2011, 3, 9–10.
- 3P. A. Gale, Chem. Commun. 2010, 47, 82–86; N. Busschaert, C. Caltagirone, W. Van Rossom, P. A. Gale, Chem. Rev. 2015, 115, 8038–8155; S. Kubik, Chem. Soc. Rev. 2010, 39, 3648–3663.
- 4N. H. Evans, P. D. Beer, Angew. Chem. Int. Ed. 2014, 53, 11716–11754; Angew. Chem. 2014, 126, 11908–11948.
- 5F. M. Ashcroft, Ion Channels and Disease, Academic Press, San Diego, USA, 2000.
- 6S. M. Rowe, S. Miller, E. J. Sorscher, N. Engl. J. Med. 2005, 352, 1992–2001; P. A. Gale, N. Busschaert, C. J. E. Haynes, L. E. Karagiannidis, I. L. Kirby, Chem. Soc. Rev. 2014, 43, 205–241.
- 7R. Custelcean, Chem. Soc. Rev. 2010, 39, 3675–3684; M.-O. M. Piepenbrock, G. O. Lloyd, N. Clarke, J. W. Steed, Chem. Rev. 2010, 110, 1960–2004; I. A. Riddell, M. M. J. Smulders, J. K. Clegg, Y. R. Hristova, B. Breiner, J. D. Thoburn, J. R. Nitschke, Nat. Chem. 2012, 4, 751–756.
- 8R. B. P. Elmes, K. A. Jolliffe, Chem. Commun. 2015, 51, 4951–4968;
S. Kubik, R. Goddard, R. Kirchner, D. Nolting, J. Seidel, Angew. Chem. Int. Ed. 2001, 40, 2648–2651;
10.1002/1521-3773(20010716)40:14<2648::AID-ANIE2648>3.0.CO;2-# CAS PubMed Web of Science® Google ScholarAngew. Chem. 2001, 113, 2722–2725.
- 9M. Amorín, L. Castedo, J. R. Granja, J. Am. Chem. Soc. 2003, 125, 2844–2845; M. Amorín, R. J. Brea, L. Castedo, J. R. Granja, Org. Lett. 2005, 7, 4681–4684; R. J. Brea, M. Amorín, L. Castedo, J. R. Granja, Angew. Chem. Int. Ed. 2005, 44, 5710–5713; Angew. Chem. 2005, 117, 5856–5859.
- 10R. García-Fandiño, M. Amorín, L. Castedo, J. R. Granja, Chem. Sci. 2012, 3, 3280–3285; J. Montenegro, C. Vázquez-Vázquez, A. Kalinin, K. E. Geckeler, J. R. Granja, J. Am. Chem. Soc. 2014, 136, 2484–2491; M. Cuerva, R. García-Fandiño, C. Vázquez-Vázquez, M. A. López-Quintela, J. Montenegro, J. R. Granja, ACS Nano 2015, 9, 10834–10843.
- 11
- 11aC. Reiriz, M. Amorín, R. García-Fandiño, L. Castedo, J. R. Granja, Org. Biomol. Chem. 2009, 7, 4358–4361;
- 11bN. Rodríguez-Vázquez, R. García-Fandiño, M. Amorín, J. R. Granja, Chem. Sci. 2016, 7, 183–187.
- 12N. Rodríguez-Vázquez, S. Salzinger, L. F. Silva, M. Amorín, J. R. Granja, Eur. J. Org. Chem. 2013, 3477–3482.
- 13A. A. Edwards, G. J. Sanjayan, S. Hachisu, G. E. Tranter, G. W. J. Fleet, Tetrahedron Lett. 2006, 62, 7718–7725.
- 14R. García-Fandiño, L. Castedo, J. R. Granja, S. Vázquez, J. Phys. Chem. B 2010, 114, 4973–4983; W. J. Hehre, L. Radom, P. von R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, 1st ed., Wiley, New York, 1986.
- 15C. T. Yang, Y. Fu, Y. B. Huang, J. Yi, Q. X. Guo, L. Liu, Angew. Chem. Int. Ed. 2009, 48, 7398–7401; Angew. Chem. 2009, 121, 7534–7537.
- 16N. Busschaert, P. A. Gale, Angew. Chem. Int. Ed. 2013, 52, 1374–1382; Angew. Chem. 2013, 125, 1414–1422; J. T. Davis, O. Okunola, R. Quesada, Chem. Soc. Rev. 2010, 39, 3843–3862.
- 17B. A. McNally, A. V. Koulov, B. D. Smith, J. B. Joos, A. P. Davis, Chem. Commun. 2005, 1087–1089; M. Lisbjerg, H. Valkenier, B. M. Jessen, H. Al-Kerdi, A. P. Davis, M. Pittelkow, J. Am. Chem. Soc. 2015, 137, 4948–4951.
- 18T. Takeuchi, N. Sakai, S. Matile, Faraday Discuss. 2009, 143, 187–203.
- 19J. N. Weinstein, S. Yoshikami, P. Henkart, R. Blumenthal, W. A. Hagins, Science 1977, 195, 489–492.
- 20CCDC 1443051 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.