C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines: a universal linker for nucleic acids modification

Tetrahedron

Volumn 64, Issue 16, 2008, Pages 3578-3588

  Saito, Yoshio ^a   Matsumoto, Katsuhiko ^a   Bag, Subhendu Sekhar ^a   Ogasawara, Shinzi ^b   Fujimoto, Kenzo ^b   Hanawa, Kazuo ^a   Saito, Isao ^a  

^a NIHON UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; DEOXYGUANOSINE; DNA Z; NUCLEIC ACID; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL MODIFICATION; CONFORMATION; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 39849086181     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.091     Document Type: Article

References (47)

1. Mitsuya H., and Broder S. Proc. Natl. Acad. Sci. U.S.A. 83 (1986) 191l
2. DeClercq E. Adv. Drug Res. 17 (1988) 1
3. Mitsuya H., Weinhold K.J., Furmau P.A., St.Clair M.H., Lehrman S.N., Gallo R.C., Bolognesi D., Barry D.W., and Broder S. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 7096
4. Sessler J.L., Sathiosatham M., Doerr K., Lynch V., and Abboud K.A. Angew. Chem., Int. Ed. 39 (2000) 1300
5. Manet I., Francini L., Masiero S., Pieraccini S., Spada G.P., and Gottarelli G. Helv. Chim. Acta 84 (2001) 2096
6. Shi X., Mullaugh K.M., Fettinger J.C., Jiang Y., Hofstadler S.A., and Davis J.T. J. Am. Chem. Soc. 125 (2003) 10830 For examples of DNA triplexes, see:
7. Moser H.E., and Dervan P.B. Science 238 (1987) 645 For examples of guanine quadruplex formation, see:
8. Davis J.T. Angew. Chem., Int. Ed. 43 (2004) 668 and references therein
9. Zahler A.M., Williamson J.R., Cech T.R., and Prescott D.M. Nature 350 (1991) 718
10. Sen D., and Gilbert W. Nature 334 (1988) 364
11. Lyonnais S., Hounsou C., Teulade-Fichou M.-P., Jeusset J., Le Cam E., and Mirambeau G. Nucleic Acids Res. 30 (2002) 5276
12. Sundquist W.I., and Heaphy S. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 3393
13. Gottarelli G., Masiero S., Mezzina E., Pieraccini S., Spada G.P., and Mariani P. Liq. Cryst. 26 (1999) 965
14. Andrisano V., Gottarreli G., Masiero S., Heijne E.H., Pieraccini S., and Spada G.P. Angew. Chem., Int. Ed. 38 (1999) 2386
15. Forman S.L., Fettinger J.C., Pieraccini S., Gottarelli G., and Davis J.T. J. Am. Chem. Soc. 122 (2000) 4060
16. Kotch F.W., Sidorov V., Lam Y.-F., Kayser K.J., Li H., Kaucher M.S., and Davis J.T. J. Am. Chem. Soc. 125 (2003) 15140
17. Gubala V., Jesus D.D., and Rivera J.M. Tetrahedron Lett. 47 (2006) 1413
18. Kwan I.C.M., She Y.-M., and Wu G. Chem. Commun. (2007) 4286
19. See Ref. 2a;
20. Giorgi T., Lena S., Mariani P., Cremonini M.A., Masiero S., Pieraccini S., Rabe J.P., Samori P., Spada G.P., and Gottarelli G. J. Am. Chem. Soc. 125 (2003) 14741
21. Sugiyama H., Kawai K., Matsunaga A., Fujimoto K., Saito I., Robinson H., and Wang A.H.-J. Nucleic Acids Res. 24 (1996) 1272
22. Xu Y., Ikeda R., and Sugiyama H. J. Am. Chem. Soc. 125 (2003) 13519
23. Sessler J.L., Jayawickramarajah J., Sathiosatham M., Sherman C.L., and Brodbelt J.S. Org. Lett. 5 (2003) 2627
24. Sessler J.L., Jayawickramarajah J., Sherman C.L., and Brodbelt J.S. J. Am. Chem. Soc. 126 (2004) 11460
25. Davis J.T., and Spada G.P. Chem. Soc. Rev. 36 (2007) 296
26. Gubala V., Betancourt J.E., and Rivera J.M. Org. Lett. 6 (2004) 4735
27. N-Propargyltrifluoroacetamide substituted 2′-deoxyguanosine is reported. See reference:. Garg N.K., Woodroofe C.C., Lacenere C.J., Quake S.R., and Stoltz B.M. Chem. Commun. (2005) 4551
28. Saito Y., Hanawa K., Kawasaki N., Bag S.S., and Saito I. Chem. Lett. 35 (2006) 1182
29. Okamoto A., Tainaka K., and Saito I. J. Am. Chem. Soc. 125 (2003) 4972
30. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
31. Rinkel L.J., and Altona C. J. Biomol. Struct. Dyn. 4 (1987) 621
32. Rosemeyer H., Toth G., Golankiewicz B., Kazimierczuk Z., Bourgeois W., Kretschmer U., Muth H.P., and Seela F. J. Org. Chem. 55 (1990) 5784
33. Gannett P.M., and Heavner S. J. Biomol. Struct. Dyn. 23 (2005) 203
34. Brazier J.A., Shibata T., Townsley J., Taylor B.F., Frary E., Williams N.H., and Williams D.M. Nucleic Acids Res. 33 (2005) 1362
35. He J., and Seela F. Nucleic Acids Res. 30 (2002) 5485
36. Graham D., Parkinson J.A., and Brown T. J. Chem. Soc., Perkin Trans. 1 (1998) 1131
37. Hamm M.L., Rajguru S., Downs A.M., and Cholera R. J. Am. Chem. Soc. 127 (2005) 12220
38. See Supplementary data, page S12.
39. Rich A., and Zhang S. Nat. Rev. Genet. 4 (2003) 566
40. Zacharias W., O'Connor T.R., and Larson J.E. Biochemistry 27 (1988) 2970
41. Sheridan S.D., Benham C.J., and Hatfield G.W. J. Biol. Chem. 274 (1999) 8169
42. Liu R., Liu H., Chen X., Kirby M., Brown P.O., and Zhao K. Cell 106 (2001) 309
43. Schade M., Turner C.J., Kuhne R., Schmieder P., Lowenhaupt K., Herbert A., and Rich A. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 12465
44. Schwartz T., Behlke J., Lowenhaupt K., Heinemann U., and Rich A. Nat. Struct. Biol. 8 (2001) 761
45. Pohl F.M., and Jovin T.M. J. Mol. Biol. 67 (1972) 375
46. Presler R.S., Chen H.H., Colombo M.F., Choe Y., Short Jr. B.J., and Rau D.C. Biochemistry 34 (1995) 14400
47. Saenger W., Hunter W.N., and Kennard O. Nature 324 (1986) 385