A remarkable adenine-binding cleft based on a hydroxyimide scaffold

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7861-7864

  Lonergan, David G ^a   Deslongchamps, Ghislain ^a   Tomàs, Salvador ^b  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032558669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01759-6     Document Type: Article

References (37)

1. 1. (a) "Molecular Recognition", Gellman, S.H. Ed., Chem. Rev. 1997, 97, 1231-1734.
2. (b) Hamilton, A.D. Ed. Tetrahedron (Symposia-in-print number 56) 1995, 51, 343-648.
3. 2. For example, see (a) Kato, Y.; Conn, M.M.; Rebek, J.Jr. Proc. Natl. Acad. Sci. USA 1995, 92, 1208-1212.
4. (b) Kato, Y.; Conn, M.M.; Rebek, Jr., J. J. Am. Chem. Soc., 1994, 116, 3279-3284
5. (c) Conn, M.M.; Deslongchamps, G.; de Mendoza, J.; Rebek Jr., J., J. Am. Chem. Soc., 1993, 115, 3548-3557.
6. (d) Tjivikua, T.; Deslongchamps, G.; Rebek, J. Jr. J. Am. Chem. Soc., 1990, 112, 8408-8414.
7. (e) Huc, I.; Rebek, J. Jr. Tetrahedron Lett, 1994, 35, 1035-1038.
8. (f) Jeong, K.-S.; Cho, Y.L. Tetrahedron Lett. 1997, 38, 8337-8340.
9. 3. Tsao, B.L.; Pieters, R.J.; Rebek, J. Jr. J. Am. Chem. Soc., 1995, 117, 2210-2213.
10. 4. (a) Curran, D.P.; Jeong, K.-S.; Heffner, T.A.; Rebek, J. Jr. J. Am. Chem. Soc., 1989, 111, 9238-9240.
11. (b) Jeong, K.-S.; Parris, K.; Rebek, J.Jr. Angew. Chem. Int. Ed. Engl. 1990, 29, 555-556.
12. 5. a) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. SYNLETT 1997, 411-420.
13. (b) Potin, D.; Williams, K.; Rebek, J.Jr. Angew. Chem. Int. Ed. Engl. 1990, 29, 1420.
14. 6. Andreu, C.; Galán, A.; Kobiro, K.; de Mendoza, J.; Park, T.K.; Rebek, J.Jr.; Salmerón, A.; Usman, N. J. Am. Chem. Soc. 1994, 116, 5501-5502.
15. 7. Wang, Z.-H.; Hirose, T.; Baldwin, B.W.; Yang, Y. J Chem. Soc. Chem. Commun. 1997, 297-298 and references therein.
16. 8. Wintner, E.A.; Rebek, J. Jr. Acta Chem. Scand. 1996, 50, 469-485.
17. 9. Kato, Y.; Toledo, L.M.; Rebek, J. Jr. J. Am. Chem. Soc. 1996, 118, 8575-8579.
18. 10. Kocis, P.; Issakova, O.; Sepetov, N.F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623-6626.
19. 11. (a) Lonergan, D.G.; Riego, J.; Deslongchamps, G. Tetrahedron Lett. 1996, 37, 6109-6112.
20. (b) Lonergan, D.G.; Deslongchamps, G., submitted to Tetrahedron.
21. 12. An alternative hydroxyimide scaffold was reported recently, see Caycho, J.R.; Garcia-Tellado, F.; de Armas, P.; Marrero-Tellado, J.J. Tetrahedron Lett. 1997, 38, 7911-7912.
22. 13. Myles, A. CHEM-4000 Honours thesis, U.N.B., 1997.
23. 14. For a review on nucleotide recognition see Seel, C.; Galán, A.; de Mendoza, J. Top. Curr. Chem. 1995, 175, 101-132.
24. 15. Domanski, A.; Pielichowski, J. Zaszyty Naukowe/Wyzsza Szkoly Pedag. im Powstancow Slaskich w Opolu [Ser. A] Chem., 1981, 4, 5-37.
25. 16. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343-349.
26. 3 to host solutions.
27. -1.
28. 19. Smithrud, D.B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
29. 20. HOSTEST v5.1, Wilcox, C.S.; Glagovich, N.M. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 1994.
30. 21. Averaged values based on monitoring 3 different protons on 4, error represents ± σ.
31. 22. MicroCal MCS ITC system: Wiseman, T.; Williston, S.; Brandts, J.F.; Lin, L.-N. Anal. Biochem. 1989, 179, 131-137.
32. 23. Williams, D.H.; Westwell, M.S. Chem. Soc. Rev. 1998, 27, 57-63.
33. 24. Schneider, H.-J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1434.
34. 25. (a) Askew, B.; Ballester, P.; Buhr, C.; Jeong, K.-S.; Jones, S.; Parris, K., Williams, K.; Rebek J. Jr. J. Am. Chem. Soc. 1989, 111, 1082-1090.
35. (b) Williams, K.; Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Rebek J. Jr. J. Am. Chem. Soc. 1989, 111, 1090-1094.
36. 26. Hunter, C.A.; Sanders, J.K.M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
37. 27. Langlet, J.; Claverie, P.; Caron, F.; Boeuve, J.C. Int. J. Quantum Chem. 1981, 19, 299-338.