Folding directed N-oxidation of oligopyridine-dicarboxamide strands and hybridization of oxidized oligomers

Journal of the American Chemical Society

Volumn 127, Issue 8, 2005, Pages 2400-2401

  Dolain, Christel ^a   Zhan, Chuanlang ^a   Léger, Jean Michel ^b   Daniels, Lee ^c   Huc, Ivan ^a  

^a INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

^b Laboratoire de Pharmacochimie   (France)

^c Rigaku/MSC Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DICARBOXAMIDE; OLIGOMER; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; HYBRIDIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NYLONS; OXIDATION-REDUCTION; PYRIDINES;

EID: 14744268166     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0424631     Document Type: Article

References (25)

1. (a) Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J.-M. Chem.-Eur. J. 2001, 7, 2798-2809.
2. (b) Huc, I.; Maurizot, V.; Gornitzka, H.; Léger, J.-M. Chem. Commun. 2002, 578-579.
3. (a) Berl, V.; Huc, I.; Khoury, R. G.; Krische, M. J.; Lehn, J.-M. Nature 2000, 407, 720-723.
4. (b) Berl, V.; Hue, I.; Khoury, R. G.; Lehn, J.-M. Chem.-Eur. J. 2001, 7, 2810-2820.
5. (c) Maurizot, V.; Léger, J.-M.; Guionneau, P.; Huc, I. Russ. Chem. Bull., Int. Ed. 2004, 53, 1572-1576.
6. (d) Jiang, H.; Maurizot, M.; Huc, I. Tetrahedron 2004, 60, 10029-10038.
7. For artificial hybrids that do not form well-defined double helices, see: (a) Gabriel, G. J.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 15174-15175.
8. (b) Yang, X.; Martinovic, S.; Smith, R. D.; Gong, B. J. Am. Chem. Soc. 2003, 125, 9932-9933.
9. (c) Archer, E. A.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 5074-5083.
10. (d) Moriuchi, T.; Tamura, T.; Hirao, T. J. Am. Chem. Soc. 2002, 124, 9356-9357.
11. (e) Bisson, A. P.; Carver, F. J.; Eggleston, D. S.; Haltiwanger, R. C.; Hunter, C. A.; Livingstone, D. L.; MacCabe, J. F.; Rotger, C.; Rowan, A. E. J. Am. Chem. Soc. 2000, 122, 8856-8868.
12. For reviews on helicates, see: (a) Albrecht, M. Chem. Rev. 2001, 101, 3457-3498.
13. (b) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062.
14. Acocella, A.; Venturini, A.; Zerbetto, F. J. Am. Chem. Soc. 2004, 126, 2362-2367.
15. (a) Huc, I. Eur. J. Org. Chem. 2004, 17-29. Jiang, H.; Léger, J.-M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448-3449.
16. (a) Huc, I. Eur. J. Org. Chem. 2004, 17-29. Jiang, H.; Léger, J.-M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448-3449.
17. (b) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583-11588.
18. (c) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587-10593.
19. For a noticeable exception, see: Huang, B.; Parquette, J. R. Org. Lett. 2000, 2, 239-242.
20. Unpublished work from our laboratory.
21. (a) Goswami, S.; Ghosh, K.; Mahapatra, A. K.; Nigam, G. D.; Chinnakali, K.; Fun, H.-K. Acta Crystallogr. 1999, C55, 579-581.
22. (b) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529-7541.
23. Heemstra, J. M.; Moore, J. S. Chem. Commun. 2004, 1480-1481.
24. Heemstra, J. M.; Moore, J. S. J. Am. Chem. Soc. 2004, 126, 1648-1649.
25. 2 (all data) = 0.2833. The poor quality of this structure is due to weak diffraction intensity and slow crystal decomposition.