Peptide mimics by linear arylamides: A structural and functional diversity test

Accounts of Chemical Research

Volumn 41, Issue 10, 2008, Pages 1343-1353

  Li, Zhan Ting ^a   Hou, Jun Li ^a   Li, Chuang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANISOLE; ANISOLE DERIVATIVE; ANTHRACENE DERIVATIVE; BIOMIMETIC MATERIAL; CATENANE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; HYDROGEN BOND; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMIDES; ANISOLES; ANTHRACENES; BIOMIMETIC MATERIALS; CIRCULAR DICHROISM; HYDROGEN BONDING; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES;

EID: 57149145479     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700219m     Document Type: Article

References (57)

1. Seebach, D.; Matthews, J. L. β-Peptides: A Surprise at Every Turn. Chem. Commun. 1997, 2015-2022.
2. Gellman, S. H. Foldamers: A Manifesto. Acc. Chem. Res. 1998, 31, 173-180.
3. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. β-Peptides: From Structure to Function. Chem. Rev. 2001, 101, 3219-3232.
4. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. A Field Guide to Foldamers. Chem. Rev. 2001, 101, 3893-4011.
5. Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Foldamers as Versatile Frameworks for the Design and Evolution of Function. Nat. Chem. Biol. 2007, 3, 252-262.
6. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. β- Peptide Foldamers: Robust Helix Formation in a New Family of β-Amino Acid Oligomers. J. Am. Chem. Soc. 1996, 118, 13071-13072.
7. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. β-Peptides. Synthesis by Amdt-Eistert Homologation with Concomitant Peptide Coupling. Structure Determination by NMR and CD Spectroscopy and by X-Ray Crystallography. Helical Secondary Structure of a β-Hexapeptide in Solution and Its Stability towards Pepsin. Helv. Chim. Acta 1996, 79, 913-941.
8. Gong, B. Crescent Oligoamides: From Acyclic "Macrocycles" to Folding Nanotubes. Chem. - Eur. J. 2001, 7, 4337-4342.
9. Huc, I. Aromatic Oligoamide Foldamers. Eur. J. Org. Chem. 2004, 17-29.
10. Sanford, A.; Yamato, K.; Yang, X. W.; Yuan, L. H.; Han, Y. H.; Gong, B. Well-Defined Secondary Structures: Information-Storing Molecular Duplexes and Helical Foldamers Based on Unnatural Peptide Backbones. Eur. J. Biochem. 2004, 271, 1416-1425.
11. 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.
12. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. Oligoanthranilamides. Non-Peptide Subunits That Show Formation of Specific Secondary Structure. J. Am. Chem. Soc. 1996, 118, 7529-7541.
13. Berl, V.; Huc, I.; Khoury, R. G.; Krische, M. J.; Lehn, J.-M. Interconversion of Single and Double Helices Formed from Synthetic Molecular Strands. Nature 2000, 407, 720-723.
14. Zhu, J.; Parra, R. D.; Zeng, H.; Skrzypczak-Jankun, E.; Zeng, X. C.; Gong, B. A New Class of Folding Oligomers: Crescent Oligoamides. J. Am. Chem. Soc. 2000, 122, 4219-4220.
15. Jiang, H.; Léger, J.-M.; Huc, I. Aromatic δ-Peptides. J. Am. Chem. Soc. 2003, 125, 3448-3449.
16. Corbin, P. S.; Zimmerman, S. C.; Thiessen, P. A.; Hawryluk, N. A.; Murray, T. J. Complexation-Induced Unfolding of Heterocyclic Ureas. Simple Foldamers Equilibrate with Multiply Hydrogen-Bonded Sheetlike Structures. J. Am. Chem. Soc. 2001, 123, 10475-10488.
17. Sinkeldam, R. W.; van Houtem, M. H. C. J.; Pieterse, K.; Vekemans, J. A. J. M.; Meijer, E. W. Chiral Poly(ureidophthalimide) Foldamers in Water. Chem. - Eur. J. 2006, 12, 6129-6137.
18. Baruah, P. K.; Gonnade, R.; Rajamohanan, P. R.; Hofmann, H.-J.; Sanjayan, G. J. BINOL-Based Foldamers-Access to Oligomers with Diverse Structural Architectures. J. Org. Chem. 2007, 72, 5077-5084.
19. Ernst, J. T.; Becerril, J.; Park, H. S.; Yin, H.; Hamilton, A. D. Design and Application of an α-Helix-Mimetic Scaffold Based on an Oligoamide-Foldamer Strategy: Antagonism of the Bak BH3/Bcl-xL Complex. Angew. Chem., Int. Ed. 2003, 42, 535-539.
20. Vögtle, F.; Weber, E. Multidentate Acyclic Neutral Ligands and Their Complexation. Angew. Chem., Int. Ed. Engl. 1979, 18, 753-776.
21. Berl, V.; Krische, M. J.; Huc, I.; Lehn, J.-M.; Schmutz, M. Template-Induced and Molecular Recognition Directed Hierarchical Generation of Supramolecular Assemblies from Molecular Strands. Chem. - Eur. J. 2000, 6, 1938-1946.
22. Prince, R. B.; Barnes, S. A.; Moore, J. S. Foldamer-Based Molecular Recognition. J. Am. Chem. Soc. 2000, 122, 2758-2762.
23. Stone, M. T.; Heemstra, J. M.; Moore, J. S. The Chain-Length Dependence Test. Acc. Chem. Res. 2006, 39, 11-20.
24. Yi, H.-P.; Li, C.; Hou, J.-L.; Jiang, X.-K.; Li, Z.-T. Hydrogen-Bonding-Induced Oligoanthranilamide Foldamers. Synthesis, Characterization, and Complexation for Alkyl Ammonium Ions. Tetrahedron 2005, 61, 7974-7980.
25. 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.
26. 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.
27. Yi, H.-P.; Shao, X.-B.; Hou, J.-L.; Li, C.; Jiang, X.-K.; Li, Z.-T. Hydrogen-Bonding-Mediated Oligoanthranilamide Foldamer Receptors That Efficiently Bind a Triol and Saccharides in Chloroform. New J. Chem. 2005, 29, 1213-1218.
28. Dunitz, J. D. Organic Fluorine: Odd Man Out. ChemBioChem 2004, 5, 614-621.
29. Zhu, Y.-Y.; Wu, J.; Li, C.; Zhu, J.; Hou, J.-L.; Li, C.-Z.; Jiang, X.-K.; Li, Z.-T. F⋯H-N and MeO⋯H-N Hydrogen-Bonding in the Solid States of Aromatic Amides and Hydrazides. A Comparison Study. Cryst. Growth Des. 2007, 7, 1490-1486.
30. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Dialkylammonium Ion/Crown Ether Complexes: The Forerunners of a New Family of Interlocked Molecules. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865-1869.
31. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Molecular Encapsulation. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
32. Brunsveld, L.; Folmer, B. J.; Meijer, E. W.; Sijbesma, R. P. Supramolecular Polymers. Chem. Rev. 2001, 101, 4071-4098.
33. Nowick, J. S. Chemical Models of Protein β-Sheets. Acc. Chem. Res. 1999, 32, 287-296.
34. Zhao, X.; Wang, X.-Z.; Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. Novel Hydrazide-Based Quadruply Hydrogen Bonded Heterodimers. Structure, Assembling Selectivity and Supramolecular Substitution. J. Am. Chem. Soc. 2003, 125, 15128-15139.
35. 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.
36. Maurizot, C.; Dolain, C.; Leydet, Y.; Léger, J.-M.; Guionneau, P.; Huc, I. Design of an Inversion Center between Two Helical Segments. J. Am. Chem. Soc. 2004, 126, 10049-10052.
37. Cram, D. J. The Design of Molecular Hosts, Guests, and Their Complexes. Angew. Chem., Int. Ed Engl. 1988, 27, 1009-1020.
38. Yi, H.-P.; Wu, J.; Ding, K.-L.; Jiang, X.-K.; Li, Z.-T. Hydrogen Bonding-Induced Aromatic Oligoamide Foldamers as Spherand Analogues to Accelerate the Hydrolysis of Nitro-Substituted Anisole in Aqueous Media. J. Org. Chem. 2007, 72, 870-877.
39. Wu, Z.-Q.; Jiang, X.-K.; Zhu, S.-Z.; Li, Z.-T. Hydrogen Bond-Induced Rigid Oligoanthranilamide Ribbons That Are Planar and Straight. Org. Lett. 2004, 6, 229-232.
40. Zhu, J.; Wang, X.-Z.; Chen, Y.-Q.; Jiang, X.-K.; Chen, X.-Z.; Li, Z.-T. Hydrogen Bonding-Induced Planar, Rigid, and Zigzag Oligoanthranilamides. Synthesis, Characterization, and Self-Assembly of a Metallocyclophane. J. Org. Chem. 2004, 69, 6221-6227.
41. Wu, Z.-Q.; Jiang, X.-K.; Li, Z.-T. Hydrogen Bonding-Mediated Self-Assembly of Square and Triangular Metallocyclophanes. Tetrahedron Lett. 2005, 46, 8067-8070.
42. Chen, Y.-Q.; Wang, X.-Z.; Shao, X.-B.; Hou, J.-L.; Chen, X.-Z.; Jiang, X.-K.; Li, Z.-T. Hydrogen Bonding-Mediated Self-Assembly of Rigid and Planar Metallocyclophanes and Their Recognition for Mono- and Disaccharides. Tetrahedron 2004, 60, 10253-10260.
43. Lin, J.-B.; Xu, X.-N.; Li, Z.-T. Unpublished results.
44. Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang, X.-K.; Li, Z.-T. Hydrogen-Bonding-Mediated Anthranilamide Homoduplexes. Increasing Stability through Preorganization and Iterative Arrangement of Simple Amide Binding Sites. J. Am. Chem. Soc. 2006, 128, 12307-12313.
45. Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Jiang, X.-K.; Li, Z.-T. Hydrogen Bonding-Mediated Self-Assembly of Anthranilamide-Based Homodimers through Preorganization of the Amido and Ureido Binding Sites. Tetrahedron 2006, 62, 11933-11941.
46. Wu, Z.-Q.; Shao, X.-B.; Li, C.; Hou, J.-L.; Wang, K.; Jiang, X.-K.; Li, Z. T. Hydrogen Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C60, C70 and C60 Derivatives. J. Am. Chem. Soc. 2005, 127, 17460-17468.
47. 2 in Aqueous and Polar Organic Media. Tetrahedron Lett. 2007, 48, 7327-7331.
48. Wu, Z.-Q.; Li, C.-Z.; Feng, D.-J.; Jiang, X.-K.; Li, Z.-T. Foldamer-Based Pyridine-Fullerene Tweezer Receptors for Increased Binding of Zinc Porphyrin. Tetrahedron 2006, 62, 11054-11062.
49. Hou, J.-L.; Yi, H.-P.; Shao, X.-B.; Li, C.; Wu, Z.-Q.; Jiang, X.-K.; Wu, L.-Z.; Tung, C.-H.; Li, Z.-T. Helicity Induction in Hydrogen Bonding-Driven Zinc Porphyrin Foldamers by Chiral C60-Incorporated Histidines. Angew. Chem., Int. Ed. 2006, 45, 796-800.
50. Li, C.-Z.; Zhu, J.; Wu, Z.-Q.; Hou, J.-L.; Li, C.; Shao, X.-B.; Jiang, Li, Z.-T.; Gao, X.; Wang, Q.-R. "Two-Point"-Bound Supramolecular Complexes from Semi-Rigidified Dipyridine Receptors and Zinc Porphyrins. Tetrahedron 2006, 62, 6973-6980.
51. Feng, D.-J.; Wang, G.-T.; Wu, J.; Wang, R.-X.; Li, Z.-T. Hydrogen Bonding-Driven Elastic Bis(zinc)porphyrin Receptors for Neutral and Cationic Electron-Deficient Guests with a Sandwich-Styled Complexing Pattern. Tetrahedron Lett. 2007, 48, 6181-6185.
52. Li, C.; Zhu, Y.-Y.; Yi, H.-P.; Li, C.-Z.; Jiang, X.-K.; Li, Z.-T. Strong Stacking between Hydrogen Bonded Foldamers and Fullerenes: Formation of Supramolecular Nano Networks. Chem. - Eur. J. 2007, 13, 9990-9998.
53. Wu, J.; Hou, J.-L.; Li, C.; Wu, Z.-Q.; Jiang, X.-K.; Li, Z.-T.; Yu, Y.-H. Dynamic [2]Catenanes Based on Hydrogen Bonding-Mediated Bis-Zinc Porphyrin Foldamer Tweezer: a Case Study. J. Org. Chem. 2007, 72, 2897-2905.
54. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Dynamic Combinatorial Chemistry. Chem. Rev. 2006, 106, 3652-3711.
55. Zimmerman, S. C. Rigid Molecular Tweezers as Hosts for the Complexation of Neutral Guests. Top. Curr. Chem. 1993, 165, 71-102.
56. 60. J. Am. Chem. Soc. 1999, 121, 9477-9478.
57. Yuan, L.; Zeng, H.; Yamato, K.; Sanford, A. S.; Feng, W.; Atreya, H. S.; Sukumaran, D. K.; Szyperski, T.; Gong, B. Helical Aromatic Oligoamides: Reliable, Readily Predictable Folding from the Combination of Rigidified Structural Motifs. J. Am. Chem. Soc. 2004, 126, 16528-16537.