Synthesis and conformational studies of amide-linked cyclic homooligomers of a thymidine-based nucleoside amino acid

Tetrahedron

Volumn 61, Issue 40, 2005, Pages 9506-9512

  Chakraborty, Tushar Kanti ^a   Koley, Dipankar ^a   Prabhakar, Sripadi ^a   Ravi, Rapolu ^a   Kunwar, Ajit Chand ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Conformation; Cyclic DNAs; Cyclic peptides; Cyclic RNAs; NMR; Nucleoside amino acids

Indexed keywords

AMIDE; AMINO ACID; BIOPOLYMER; DIMER; NUCLEOSIDE; OLIGOMER; THYMIDINE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 27744432389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.089     Document Type: Article

References (64)

1. (a) Deber, C. M.; Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106-113.
2. (b) Milner-White, E. J. Trends Pharmacol. Sci. 1989, 10, 70-74.
3. (c) Fairlie, D. P.; Abbenante, G.; March, D. R. Curr. Med. Chem. 1995, 2, 654-686.
4. (d) Cuniasse, P.; Raynal, I.; Yiotakis, A.; Dive, V. J. Am. Chem. Soc. 1997, 119, 5239-5248.
5. (e) Cavallaro, V.; Thompson, P.; Hearn, M. J. Pept. Sci. 1998, 4, 335-343.
6. (f) Benito, J. M.; Blanco, J. L. J.; Mellet, C. O.; Fernández, J. M. G. Angew. Chem., Int. Ed. 2002, 41, 3674-3676.
7. (g) Fan, L.; Hindsgaul, O. Org. Lett. 2002, 4, 4503-4506.
8. (h) Jaunzems, J.; Oelze, B.; Kirschning, A. Org. Biomol. Chem. 2004, 2, 3448-3456.
9. (i) Kazmaier, U.; Hebach, C.; Watzke, A.; Maier, S.; Mues, H.; Volker Hu, V. Org. Biomol. Chem. 2005, 3, 136-145.
10. (a) Hsu, C.-Y.L.; Dennis, D. Nucleic Acids Res. 1982, 10, 5637-5647.
11. (b) Ulanovsky, L.; Bodner, M.; Trifonov, E. N.; Choder, M. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 862-866.
12. (c) Ross, P.; Weinhouse, H.; Aloni, Y.; Michaeli, D.; Weinberg-Ohana, P.; Mayer, R.; Braun, S.; de Vroom, E.; van der Marel, G. A.; van Boom, J. H.; Benziman, M. Nature 1987, 325, 279-290.
13. (d) Rao, M. V.; Reese, C. B. Nucleic Acids Res. 1989, 17, 8221-8239.
14. (e) Rumney, S., IV; Kool, E. T. Angew. Chem., Int. Ed. Engl. 1992, 31, 1617-1619.
15. (f) Prakash, G.; Kool, E. T. J. Am. Chem. Soc. 1992, 114, 3523-3527.
16. (g) Gamper, H. B.; Reed, M. W.; Cox, T.; Virosco, J. S.; Adams, A. D. Nucleic Acids Res. 1993, 21, 145-150.
17. (h) Diener, T. O. Trends Microbiol. 1993, 1, 289-294.
18. (i) Rubin, E.; Rumney, S.; Kool, E. T. Nucleic Acids Res. 1995, 23, 3547-3553.
19. (j) Kool, E. T. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 1-28.
20. (k) Mazumder, A.; Uchida, H.; Neamati, N.; Sunder, S.; Jaworska-Maslanka, M.; Wickstrom, E.; Zeng, F.; Jones, R. A.; Mandes, R. F.; Chenault, H. K.; Pommier, Y. Mol. Pharmacol. 1997, 51, 567-575.
21. (l) Kool, E. T. Acc. Chem. Res. 1998, 31, 502-510.
22. (m) Escaja, N.; Pedroso, E.; Rico, M.; Gonzalez, C. J. Am. Chem. Soc. 2000, 122, 12732-12742.
23. (n) Li, T.; Liu, D.; Chen, J.; Lee, A. H. F.; Qi, J.; Chan, A. S. C. J. Am. Chem. Soc. 2001, 123, 12901-12902.
24. (a) Hsu, C.-Y. J.; Dennis, D.; Jones, R. A. Nucleosides Nucleotides 1985, 4, 377-389.
25. (b) Barbato, S.; De Napoli, L.; Mayol, L. Tetrahedron Lett. 1987, 28, 5727-5728.
26. (c) Capobianco, M. L.; Carcuro, A.; Tondelli, L.; Garbesi, A.; Bonara, G. M. Nucleic Acids Res. 1990, 18, 2661-2669.
27. (d) Ross, P.; Mayer, R.; Weinhouse, H.; Amikam, D.; Huggirat, Y.; Benziman, M.; de Vroom, E.; Fidder, A.; de Paus, P.; Sliedregt, L. A. J.; van der Marel, G. A.; van Boom, J. H. J. Biol. Chem. 1990, 265, 18933-18943.
28. (e) De Napoli, L.; Montesarchio, D.; Picciall, G.; Santacroce, C.; Mayol, L.; Galeone, A.; Messere, A. Gazz. Chim. Ital. 1991, 121, 505-508.
29. (f) Battistini, C.; Fustinoni, S. Tetrahedron 1993, 49, 1115-1132.
30. (g) Zeng, F.; Jones, R. A. Nucleosides Nucleotides 1996, 15, 1679-1686.
31. (h) Alazzouzi, E.; Escaja, N.; Grandas, A.; Pedroso, E. Angew. Chem., Int. Ed. 1997, 36, 1506-1508.
32. (i) Frieden, M.; Grandas, A.; Pedroso, E. Chem. Commun. 1999, 1593-1594.
33. (j) Smietana, M.; Kool, E. T. Angew. Chem., Int. Ed. 2002, 41, 3704-3707.
34. (k) Smietana, M.; Johnson, R. B.; Wang, Q. M.; Kool, E. T. Chem. Eur. J. 2004, 10, 173-181.
35. (a) Lebreton, J.; Mesmaeker, A. D.; Waldner, A.; Fritsch, V.; Wolf, R. M.; Freiser, S. M. Tetrahedron Lett. 1993, 34, 6383-6386.
36. (b) Lebreton, J.; Waldner, A.; Fritsch, V.; Wolf, R. M.; Mesmaeker, A. D. Tetrahedron Lett. 1994, 35, 5225-5228.
37. (c) Mesmaeker, A. D.; Lebreton, J.; Waldner, A.; Fritsch, V.; Wolf, R. M. Bioorg. Med. Chem. Lett. 1994, 4, 873-878.
38. (d) Mesmaeker, A. D.; Waldner, A.; Lebreton, J.; Hoffmann, P.; Fritsch, V.; Wolf, R. M.; Freier, S. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 226-229.
39. (e) Bergmann, F.; Bannwarth, W.; Tam, S. Tetrahedron Lett. 1995, 36, 6823-6826.
40. (f) Waldner, A.; Mesmaeker, A. D.; Wendenborn, S. Bioorg. Med. Chem. Lett. 1996, 6, 2363-2366.
41. (g) Mesmaeker, A. D.; Lesueur, C.; Bevierre, M.-O.; Fritsch, V.; Wolf, R. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2790-2794.
42. (h) Fujii, M.; Yamamoto, K.; Hidaka, J. Tetrahedron Lett. 1997, 38, 417-420.
43. (i) Mesmaeker, A. D.; Leberton, J.; Jouanno, C.; Fritsch, V.; Wolf, R. M.; Wendeborn, S. Synlett 1997, 1287-1290.
44. (j) Goodnow, R. A., Jr.; Richou, A.-R.; Tam, S. Tetrahedron Lett. 1997, 38, 3195-3198.
45. (k) Goodnow, R. A., Jr.; Tam, S.; Pruess, D. L.; McComas, W. W. Tetrahedron Lett. 1997, 38, 3199-3202.
46. (l) Robins, M.; Doboszewski, B.; Nilsson, B. L.; Peterson, M. A. Nucleosides Nucleotides Nucleic Acids 2000, 19, 69-86.
47. (m) Wilds, C. J.; Minasov, G.; Natt, F.; von Matt, P.; Altmann, K.-H.; Egli, M. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 991-994.
48. (n) Li, X.; Zhan, Z.-Y.J.; Knipe, R.; Lynn, D. G. J. Am. Chem. Soc. 2002, 124, 746-747.
49. (o) Li, X.; Lynn, D. G. Angew. Chem., Int. Ed. 2002, 41, 4567-4569.
50. 2Et (Ref. 6). The resulting product A was then transformed into 5b following the earlier reported steps (Ref. 4h). Treatment of 5b with BOM-Cl in the presence of DBU gave 5a in 85% yield (Diagram presented)
51. Lerner, C.; Siegrist, R.; Schweizer, E.; Diederich, F.; Gramlich, V.; Jakob-Roetne, R.; Zurcher, G.; Borroni, E. Helv. Chim. Acta 2003, 86, 1045-1062.
52. (a) Bruins, A. P.; Covey, T. R.; Henion, J. D. Anal. Chem. 1987, 59, 2642-2646.
53. (b) Iribane, J. V.; Thomson, B. A. J. Chem. Phys. 1976, 64, 2287-2294.
54. Cole, R. B. Electrospray Ionization Mass Spectrometry; Wiley: New York, 1997.
55. (a) Cavanagh, J.; Fairbrother, W. J.; Palmer, A. G., III; Skelton, N. J. Protein NMR Spectroscopy; Academic: San Diego, 1996.
56. (b) Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
57. Hwang, T. L.; Shaka, A. J. J. Am. Chem. Soc. 1992, 114, 3157-3159.
58. de Leeuw, F. A. A. M.; Altona, C. Quant. Chem. Progr. Exch., No. 463, University of Indiana at Bloomington, 1983.
59. Saenger, W. Principles of Nucleic Acid Structure; Springer: New York, 1984.
60. Kessler, H.; Griesinger, C.; Lautz, J.; Müeller, A.; van Gunsteren, W. F.; Berendsen, H. J. C. J. Am. Chem. Soc. 1988, 110, 3393-3396.
61. Etezady-Esfarjani, T.; Hilty, C.; Wüthrich, K.; Rueping, M.; Schreiber, J.; Seebach, D. Helv. Chim. Acta 2002, 85, 1197-1209.
62. States, D. J.; Haberkorn, R. A.; Ruben, D. J. J. Magn. Reson. 1982, 48, 286-292.
63. For details see: (a) Sybyl Force Field Manual, version 6.6, 1999, pp 217-229 (http://www.tripos.com/custResources/applicationNotes/triad/index.html).
64. (b) Evans, J. N. S. Biomolecular NMR Spectroscopy; Oxford University Press: Oxford, 1995.