Aromatic oligoamide foldamers:A paradigm for structure - property relationship

Current Organic Chemistry

Volumn 15, Issue 9, 2011, Pages 1293-1301

  Gan, Quan ^a   Wang, Ying ^a   Jiang, Hua ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Aromatic oligoamides; Foldamers; Helical capsules; Helices; Hydrogen bonds; Self assembly

Indexed keywords

AMPHIPHILES; AROMATIC COMPOUNDS; AROMATIZATION; BIOPOLYMERS; HYDROGEN BONDS; OLIGOMERS; STRUCTURAL PROPERTIES;

AROMATIC OLIGOAMIDE; FOLDAMERS; HELICAL CAPSULE; HELICAL STRUCTURES; HELIX; HYDROGEN BINDING; INTRAMOLECULAR HYDROGEN; PROPERTY; SECONDARY STRUCTURES; STRUCTURE-PROPERTIES RELATIONSHIPS;

SELF ASSEMBLY;

EID: 79958210846     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795378227     Document Type: Article

References (54)

1. Gellman, S. H. Foldamers: A Manifesto. Acc. Chem. Res., 1998, 31, 173-180.
2. Gong, B. Crescent oligoamides: from acyclic"macrocycles" to folding nanotubes. Chem. Eur. J., 2001, 7, 4336-4342.
3. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. A field guide to foldamers. Chem. Rev., 2001, 101, 3893-4012.
4. Cubberley, M. S.; Iverson, B. L. Models of higher-order structure: foldamers and beyond. Curr. Opin. Chem. Biol., 2001, 5, 650-653.
5. Schmuck, C. Molecules with helical structure: how to build a molecular spiral staircase. Angew. Chem. Int. Ed., 2003, 42, 2448-2452.
6. Huc, I. Aromatic oligoamide foldamers. Eur. J. Org. Chem., 2004, 17-29.
7. Cheng, R. P. Beyond de novo protein design - de novo design of non-natural folded oligomers. Curr. Opin. Chem. Biol., 2004, 14, 512-520.
8. Googman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Foldamers as versatile frameworks for the design and evolution of function. Nature Chemical Biology, 2007, 3, 252-262.
9. Li, Z. T.; Hou, J. L.; Li, C. Peptide mimics by Linear arylamides: a structural and functional diversity test. Acc. Chem. Res., 2008, 41, 1343-1353.
10. Seebach, D.; Hook, D. F.; Glattli, A. Helices and other secondary structures of β- and γ-peptides. Biopolymers, 2006, 84, 23-37.
11. Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. Design of secondary structures in unnatural peptides: stable helical γ-Tetra-, Hexa-, and octapeptides and consequences of [1]-substitution. J. Am. Chem. Soc., 1998, 120, 8569-8570.
12. Arndt, H. D.; Ziemer, B.; Koert, U. Folding propensity of cyclohexylether-[1] -peptides. Org. Lett. 2004, 6, 3269-3272.
13. Huc, I.; Maurizot, V.; Gornitzka, H.; Leger, J. M. Hydroxy-substituted oligopyridine dicarboxamide helical foldamers. Chem.Comm., 2002, 578-579.
14. Dolain, C.; Maurizot, V.; Huc, I. Protonation-induced transition between two distinct helical conformations of a synthetic oligomer via a linear intermediate. Angew. Chem. Int. Ed., 2003, 42, 2738-2740.
15. Gong, B.; Zeng H.; Zhu J.; Yuan L.; Han Y.; Cheng S.; Furukawa M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Jankun, E.S.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Creating nanocavities of tunable sizes: hollow helices. Proc. Natl. Acad. Sci. U.S.A., 2002, 99, 11583-11588.
16. Jiang, H.; Leger, J. M.; Huc, I. Aromatic δ-Peptides. J. Am. Chem. Soc., 2003, 125, 3448-3449.
17. Li, Z. T.; Hou, J. L.; Li, C.; Yi, H. P. Shape-persistent aromatic amide oligomers: new tools for supramolecular chemistry. Chem. Asian J., 2006, 1, 766-778.
18. Li, C.; Ren, S.-F.; Hou, J.-L.; Yi, H.-P.; Zhu, S.-Z.; Jiang, X.-K.; Li,Z.-T. F···H-N hydrogen bonding driven foldamers: efficient receptors for dialkylammonium ions. Angew. Chem., Int. Ed., 2005, 44, 5725-5729.
19. Gabriel, G. J.; Iverson, B. L. Aromatic Oligomers that Form hetero duplexes in aqueous solution. J. Am. Chem. Soc., 2002, 124, 15174-15175.
20. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Solvophobically driven folding of nonbiological oligomers. Science, 1997, 277, 1793-1796.
21. Hill, D. J.; Moore, J. S. Supramolecular chemistry and self-assembly special feature: helicogenicity of solvents in the conformational equilibrium of oligo (m -phenylene ethynylene)s: Implications for foldamer research. Proc. Natl. Acad. Sci. U.S.A., 2002, 99, 5053-5057.
22. Oh, K.; Jeong, K. S.; Moore, J. S. Folding-driven synthesis of oligomers. Nature, 2001, 414, 889-893.
23. Juwarker, H.; Lenhardt, J. M.; Pham, D. M.; Craig, S. L. 1,2,3-Triazole CH.Cl- contacts guide anion binding and concomitant folding in 1,4-diaryl triazole oligomers. Angew. Chem. Int. Ed., 2008, 47, 3740-3743.
24. Cuccia, L. A.; Ruiz, E.; Lehn, J.-M.; Homo, J. C.; Schmutz, M. Helical selforganization and hierarchical self-assembly of an oligoheterocyclic pyridinepyridazine strand into extended supramolecular fibers. Chem. Eur. J., 2002, 8, 3448-3457.
25. Saraogi, I.; Hamilton, A. D. Recent advances in the development of arylbased foldamers. Chem. Soc. Rev., 2009, 38, 1726-1743.
26. Haldar, D.; Schmuck, C. Metal-free double helices from abiotic backbones. Chem. Soc. Rev., 2009, 38, 363-371.
27. Berl, V.; Khoury, R. G.; Huc, I.; Krische, M. J.; Lehn, J.-M. Interconversion of single and double helices formed from synthetic molecular strands. Nature, 2000, 407, 720-723.
28. Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J.-M. Helical molecular programming: folding of oligopyridine-dicarboxamides into molecular single helices. Chem. Eur. J., 2001, 7, 2798-2809.
29. Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J.-M. Helical molecular programming: supramolecular double helices by dimerization of helical oligopyridine- dicarboxamide strands. Chem. Eur. J., 2001, 7, 2810-2820.
30. Baptiste, B.; Zhu, J.; Haldar, D.; Kauffmann, B.; Léger, J.-M.; Huc, I. Hybridization of long pyridine-dicarboxamide oligomers into multi-turn double helices: slow strand association and dissociation, solvent dependence, and solid state structures. Chem. Asian J. 2010, 5, 1364-1375.
31. Haldar, D.; Jiang, H.; Léger, J.-M.; Huc, I. interstrand side chain-side chain interactions in a double helical foldamer. Angew. Chem. Int. Ed., 2006, 45, 5483-5486.
32. Haldar, D.; Jiang, H.; Léger, J.-M.; Huc, I. Double versus single helical structures of oligopyridine-dicarboxamide strands. Part 2: the role of sidechain. Tetrahedron, 2007, 63, 6322-6330.
33. Berni, E.; Kauffmann, B.; Bao, C.; Lefeuvre, J.; Bassani, D. M.; Huc, I. Assessing the mechanical properties of a molecular spring. Chem. Eur. J., 2007, 13, 8463-8469.
34. Jiang, H.; Léger, J.-M.; Dolain, C.; Guionneau, P.; Huc. I. Aromatic δ- peptides: design, synthesis and structural studies of helical quinoline-derived oligoamide foldamers. Tetrahedron, 2003, 59, 8365-8374.
35. Gan, Q.; Bao, C.; Kauffmann, B.; Grelard, A.; Xiang, J.; Liu, S.; Huc, I.; Jiang, H. Quadruple and double helices of 8-fluoroquinoline oligoamides, Angew. Chem. Int. Ed., 2008, 47, 1715-1718.
36. Zhang, B.; Yuan, T.; Jiang, H.; Lei, M. Molecular dynamics simulations on the stability and assembly mechanisms of quadruple and double helical aromatic amide foldamers, J. Phys. Chem. B, 2009, 113, 10934-10941.
37. Zhu, Y. Y.; Yi, H. P.; Li, C.; Jiang, X. K.; Li, Z. T. The N-HX (X = Cl, Br and I) Hydrogen Bonding in Aromatic Amides: A Crystallographic and 1H NMR Study. Cryst. Growth Des., 2008, 8, 1294-1300.
38. Gan, Q.; Li, F.; Li, G.; Kauffmann, B.; Xiang, J.; Huc, I.; Jiang, H, Heteromeric double helix formation by cross-hybridization of chloro- and fluorosubstituted quinoline oligoamides. Chem. Comm., 2010, 46, 297-299.
39. Zhan, C. L.; Leger, J. M.; Huc, I. Cross-hybridization of pyridinedicarboxamide helical strands and their n-oxides. Angew. Chem. Int. Ed., 2006, 45, 4625-4628.
40. Li, C.; Wang, G.-T.; Yi, H.-P.; Jiang, X.-K.; Li, Z.-T.; Wang, R.-X. Diastereomeric recognition of chiral foldamer receptors for chiral glucoses. Org. Lett., 2007, 9, 1797-1800.
41. Hou, J.-L.; Shao, X.-B.; Chen, G.-J.; Zhou, Y.-X.; Jiang, X.-K.; Li, Z.-T. Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides. J. Am. Chem. Soc., 2004, 126, 12386-12394.
42. Stone, M. T.; Moore, J. S. A Water-Soluble m-Phenylene Ethynylene Foldamer. Org. Lett., 2004, 6, 469-472.
43. Goto, H.; Furusho,Y.; Yashima, E. Supramolecular control of unwinding and rewinding of a double helix of oligoresorcinol using cyclodextrin/ adamantane system. J. Am. Chem. Soc., 2007, 129, 109-112.
44. Zhao, Y.; Zhong, Z. Tuning the sensitivity of a foldamer-based mercury sensor by its folding energy. J. Am. Chem. Soc., 2006, 128, 9988-9989.
45. Wang, Y.; Li, F.; Han, Y.; Wang, F.; Jiang, H. Folding and aggregation of cationic oligo(aryl-triazole)s in aqueous solution. Chem. Eur. J., 2009, 15, 9424-9433.
46. Chang, K.-J.; Kang, B.-N.; Lee, M.-H.; Jeong, K.-S. Oligoindole-based foldamers with a helical conformation induced by chloride. J. Am. Chem. Soc., 2005, 127, 12214-12215.
47. Juwarker, H.; Lenhardt, J. M.; Pham, D. M.; Craig, S. L. 1,2,3-Triazole CH···Cl contacts guide anion binding and concomitant folding in 1,4-Diaryl triazole oligomers. Angew. Chem. Int. Ed., 2008, 47, 3740-3743.
48. Garric, J.; Leger, J. M.; Huc, I. molecular apple peels. Angew. Chem. Int. Ed., 2005, 44, 1954-1958.
49. Garric, J.; Leger, J.-M.; Huc, I. Encapsulation of small polar guests in molecular apple peels, Chem. Eur. J., 2007, 13, 8454-8462.
50. Bao, C.; Kauffmann, B.; Gan, Q.; Srinivas, K.; Jiang, H.; Huc, I. Converting sequences of aromatic amino acid monomers into function: second generation helical capsules. Angew. Chem. Int. Ed., 2008, 47, 4153-4156.
51. Bao, C.; Gan, Q.; Kauffmann, B.; Jiang, H.; Huc, I. Self-assembled foldamer capsule: combining single and double helical segments in one aromatic amide sequence. Chem. Eur. J., 2009, 15, 11530-11536.
52. Ernst, J. T.; Becerril, J.; Park, H. S.; Yin, H.; Hamilton, A. D. Design and application of an a-helix-mimetic scaffold based on an oligoamide-foldamer strategy: antagonism of the Bak BH3/Bcl-xL complex. Angew. Chem. Int. Ed., 2003, 42, 535-550.
53. Gillies, E. R.; Dolain, C.; Leger, J.-M.; Huc, I. Amphipathic helices from aromatic amino acid oligomers. J. Org. Chem., 2006, 71, 7931-7939.
54. Gillies, E. R.; Deiss, F.; Staedel, C.; Schmitter, J. M.; Huc, I. Development and biological assessment of fully water-soluble helical aromatic amide foldamers. Angew. Chem. Int. Ed., 2007, 46, 4081-4084.