Robust Helix Formation in a New Family of Oligoureas Based on a Constrained Bicyclic Building Block†
Dr. Baptiste Legrand
Laboratoire de Chimie-Physique Macromoléculaire, LCPM—UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
These authors contributed equally to this work.
Search for more papers by this authorChristophe André
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
These authors contributed equally to this work.
Search for more papers by this authorEmmanuel Wenger
Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
Search for more papers by this authorDr. Claude Didierjean
Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
Search for more papers by this authorDr. Marie Christine Averlant-Petit
Laboratoire de Chimie-Physique Macromoléculaire, LCPM—UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
Search for more papers by this authorProf. Jean Martinez
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Search for more papers by this authorCorresponding Author
Dr. Monique Calmes
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/Search for more papers by this authorCorresponding Author
Dr. Muriel Amblard
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/Search for more papers by this authorDr. Baptiste Legrand
Laboratoire de Chimie-Physique Macromoléculaire, LCPM—UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
These authors contributed equally to this work.
Search for more papers by this authorChristophe André
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
These authors contributed equally to this work.
Search for more papers by this authorEmmanuel Wenger
Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
Search for more papers by this authorDr. Claude Didierjean
Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
Search for more papers by this authorDr. Marie Christine Averlant-Petit
Laboratoire de Chimie-Physique Macromoléculaire, LCPM—UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
Search for more papers by this authorProf. Jean Martinez
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Search for more papers by this authorCorresponding Author
Dr. Monique Calmes
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/Search for more papers by this authorCorresponding Author
Dr. Muriel Amblard
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Universités Montpellier 1 et 2, 15 avenue Charles Flahault, 34000 Montpellier (France) http://www.ibmm.univ-montp1.fr/Search for more papers by this authorWe thank the CNRS, MESR and ANR (ANR-08-BLAN-0066-01) for financial support, and the SCBIM and Université de Lorraine for NMR and XRD facilities.
Graphical Abstract
Ein robustes Netz von Wasserstoffbrücken (gestrichelte Linien) verbindet die Carbonyl-Sauerstoffatome (rot) und die Aminogruppen (dunkelblau) in den starren helikalen Strukturen, die Systeme aus gespannten bicyclischen Bausteinen mit Harnstoff-Verknüpfungen bilden. Diese bicyclischen Aminocarbamoyl(BAC)-Foldamere wurden in Lösung (siehe Schema) und im Festkörper studiert.
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References
- 1S. H. Gellman, Acc. Chem. Res. 1998, 31, 173–180.
- 2D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893–4011.
- 3R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219–3232.
- 4D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodiversity 2004, 1, 1111–1239.
- 5C. M. Goodman, S. Choi, S. Shandler, W. F. DeGrado, Nat. Chem. Biol. 2007, 3, 252–262.
- 6 Foldamers: Structure, Properties, and Applications (Eds.: ), Wiley-VCH, Weinheim, 2007.
10.1002/9783527611478 Google Scholar
- 7D. Seebach, J. Gardiner, Acc. Chem. Res. 2008, 41, 1366–1375.
- 8T. A. Martinek, F. Fulop, Chem. Soc. Rev. 2012, 41, 687–702.
- 9R. J. Doerksen, B. Chen, J. Yuan, J. D. Winkler, M. L. Klein, Chem. Commun. 2003, 2534–2535.
- 10P. G. Vasudev, S. Chatterjee, N. Shamala, P. Balaram, Acc. Chem. Res. 2009, 42, 1628–1639.
- 11C. Fernandes, S. Faure, E. Pereira, V. Thery, V. Declerck, R. Guillot, D. J. Aitken, Org. Lett. 2010, 12, 3606–3609.
- 12P. G. Vasudev, S. Chatterjee, N. Shamala, P. Balaram, Chem. Rev. 2011, 111, 657–687.
- 13O. Songis, C. Didierjean, C. Laurent, J. Martinez, M. Calmes, Eur. J. Org. Chem. 2007, 3166–3172.
- 14C. André, B. Legrand, C. Deng, C. Didierjean, G. Pickaert, J. Martinez, M. C. Averlant-Petit, M. Amblard, M. Calmes, Org. Lett. 2012, 14, 960–963.
- 15V. Semetey, D. Rognan, C. Hemmerlin, R. Graff, J. P. Briand, M. Marraud, G. Guichard, Angew. Chem. 2002, 114, 1973–1975;
10.1002/1521-3757(20020603)114:11<1973::AID-ANGE1973>3.0.CO;2-J Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1893–1895.10.1002/1521-3773(20020603)41:11<1893::AID-ANIE1893>3.0.CO;2-F CAS PubMed Web of Science® Google Scholar
- 16L. Fischer, G. Guichard, Org. Biomol. Chem. 2010, 8, 3101–3117.
- 17T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983–1002.
- 18L. Guo, W. C. Zhang, A. G. Reidenbach, M. W. Giuliano, I. A. Guzei, L. C. Spencer, S. H. Gellman, Angew. Chem. 2011, 123, 5965–5968; Angew. Chem. Int. Ed. 2011, 50, 5843–5846.
- 19V. Semetey, C. Hemmerlin, C. Didierjean, A. P. Schaffner, A. G. Giner, A. Aubry, J. P. Briand, M. Marraud, G. Guichard, Org. Lett. 2001, 3, 3843–3846.
- 20M. Amblard, M. Rodriguez, J. Martinez, Tetrahedron 1988, 44, 5101–5108.
- 21M. Crisma, F. Formaggio, P. Ruzza, A. Calderan, S. Elardo, G. Borin, C. Toniolo, Biopolymers 2003, 71, 17–27.
- 22A. Violette, M. C. Averlant-Petit, V. Semetey, C. Hemmerlin, R. Casimir, R. Graff, M. Marraud, J. P. Briand, D. Rognan, G. Guichard, J. Am. Chem. Soc. 2005, 127, 2156–2164.
- 23D. A. Case, T. A. Darden, T. E. Cheatham III, C. L. Simmerling, J. Wang, R. E. Duke, R. Luo, M. Crowley, R. C. Walker, W. Zhang, K. M. Merz, B. Wang, S. Hayik, A. Roitberg, G. Seabra, I. Kolossváry, K. F. Wong, F. Paesani, J. Vanicek, X. Wu, S. R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, D. H. Mathews, M. G. Seetin, C. Sagui, V. Babin, P. A. Kollman, AMBER 10, University of California, San Francisco, 2008.
- 24V. Hornak, R. Abel, A. Okur, B. Strockbine, A. Roitberg, C. Simmerling, Proteins Struct. Funct. Bioinf. 2006, 65, 712–725.
- 25L. Fischer, P. Claudon, N. Pendem, E. Miclet, C. Didierjean, E. Ennifar, G. Guichard, Angew. Chem. 2010, 122, 1085–1088; Angew. Chem. Int. Ed. 2010, 49, 1067–1070.
- 26J. Fremaux, L. Fischer, T. Arbogast, B. Kauffmann, G. Guichard, Angew. Chem. 2011, 123, 11584–11587;
10.1002/ange.201105416 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 11382–11385.
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