8-Aza-2′-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA

Organic and Biomolecular Chemistry

Volumn 7, Issue 17, 2009, Pages 3463-3473

  Seela, Frank ^a,b   Jiang, Dawei ^a,b   Xu, Kuiying ^a,b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BASE PAIRING; BASE PAIRS; CANONICAL BASIS; DUPLEX DNA; FLUORESCENCE SENSING; GROUP PROPERTIES; NUCLEOBASES; PHOSPHORAMIDITES; SINGLE-STRANDED DNA; SOLID PHASE SYNTHESIS;

DNA; FLUORESCENCE; GENES; IONS; NUCLEIC ACIDS; OLIGONUCLEOTIDES; SYNTHESIS (CHEMICAL);

BIOMOLECULES;

DEOXYGUANOSINE; DNA; DRUG DERIVATIVE; FLUORESCENT DYE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; SINGLE STRANDED DNA;

ARTICLE; BASE MISPAIRING; BASE PAIRING; DRUG EFFECT;

BASE PAIR MISMATCH; BASE PAIRING; DEOXYGUANOSINE; DNA; DNA, SINGLE-STRANDED; FLUORESCENT DYES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 70349275267     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b908017a     Document Type: Article

References (55)

1. P. R. Callis Annu. Rev. Phys. Chem. 1983 34 329 357
2. D. C. Ward E. Reich L. Stryer J. Biol. Chem. 1969 244 1228 1237
3. S. R. Kirk N. W. Luedtke Y. Tor Bioorg. Med. Chem. 2001 9 2295 2301
4. A. Holy Collect. Czech. Chem. Commun. 1979 44 2846 2853
5. F. Seela Y. Chen U. Bindig Z. Kazimierczuk Helv. Chim. Acta 1994 77 194 202
6. F. Seela H. Steker H. Driller U. Bindig Liebigs Ann. Chem. 1987 15 19
7. F. Seela H. Steker Liebigs Ann. Chem. 1984 1719 1730
8. J. N. Wilson E. T. Kool Org. Biomol. Chem. 2006 4 4265 4274
9. J. A. Secrist III J. R. Barrio N. J. Leonard G. Weber Biochemistry 1972 11 3499 3506
10. Y. Inoue T. Kuramochi K. Imakubo Chem. Lett. 1981 1161 1164
11. J. Woo R. B. Meyer Jr. H. B. Gamper Nucleic Acids Res. 1996 24 2470 2475
12. D. A. Berry K.-Y. Jung D. S. Wise A. D. Sercel W. H. Pearson H. Mackie J. B. Randolph R. L. Somers Tetrahedron Lett. 2004 45 2457 2461
13. F. Seela E. Schweinberger K. Xu V. R. Sirivolu H. Rosemeyer E.-M. Becker Tetrahedron 2007 63 3471 3482
14. S. G. Srivatsan H. Weizman Y. Tor Org. Biomol. Chem. 2008 6 1334 1338
15. J. Ren D. J. Goss Nucleic Acids Res. 1996 24 3629 3634
16. H. Kasai M. Goto K. Ikeda M. Zama Y. Mizuno S. Takemura S. Matsuura T. Sugimoto T. Goto Biochemistry 1976 15 898 904
17. P. D. Sattsangi N. J. Leonard C. R. Frihart J. Org. Chem. 1977 42 3292 3296
18. H. Bazin X.-X. Zhou C. Glemarec J. Chattopadhyaya Tetrahedron Lett. 1987 28 3275 3278
19. F. Seela W. Bussmann Tetrahedron 1985 41 935 940
20. J. Wierzchowski B. Wielgus-Kutrowska D. Shugar Biochim. Biophys. Acta 1996 1290 9 17
21. C. P. Da Costa M. J. Fedor L. G. Scott J. Am. Chem. Soc. 2007 129 3426 3432
22. J. Davoll J. Chem. Soc. 1958 1593 1599
23. G. R. Revankar and R. K. Robins, in Chemistry of Nucleosides and Nucleotides, ed., L. B. Townsend, Plenum Press, New York, London, 1991, vol. 2, ch. 4, pp. 297-318
24. J. A. Montgomery, in Handbuch der experimentellen Pharmakologie, ed., O. Eichler, A. Farha, H. Herken, and, A. D. Welch, Springer, Heidelberg, 1974, vol. 28, p. 76
25. R. Vince M. Hua J. Med. Chem. 1990 33 17 21
26. F. Seela S. Lampe Helv. Chim. Acta 1994 77 1003 1017
27. F. Seela S. Lampe Helv. Chim. Acta 1993 76 2388 2397
28. F. Seela A. M. Jawalekar I. Münster Helv. Chim. Acta 2005 88 751 765
29. A. Albert Adv. Heterocycl. Chem. 1986 39 117 180
30. R. O. Roblin Jr. J. O. Lampen J. P. English Q. P. Cole J. R. Vaughan Jr. J. Am. Chem. Soc. 1945 67 290 294
31. G. W. Kidder V. C. Dewey R. E. Parks Jr. G. L. Woodside Science 1949 109 511 514
32. G. W. Kidder V. C. Dewey R. E. Parks Jr. G. L. Woodside Cancer. Res. 1951 11 204 211
33. R. E. F. Matthews J. D. Smith Advan. Virus. Res. 1955 3 49 148
34. J. Wierzchowski M. Ogiela B. Iwańska D. Shugar Anal. Chim. Acta 2002 472 63 74
35. J. Kára J. koda F. orm Collect. Czech. Chem. Commun. 1961 26 1386 1392
36. F. Seela K. Mersmann Helv. Chim. Acta 1993 76 2184 2193
37. W. Hutzenlaub R. L. Tolman R. K. Robins J. Med. Chem. 1972 15 879 883
38. M. H. Caruthers L. J. Mcbride L. P. Bracco J. W. Dubendorff Nucleosides Nucleotides 1985 4 95 105
39. L. G. Purnell D. J. Hodgson Organic Magnetic Resonance 1977 10 1 4
40. F. Seela W. Bussmann Nucleosides Nucleotides 1985 4 391 394
41. F. Seela H. Driller Nucleic Acids Res. 1986 14 2319 2332
42. T. Brown W. N. Hunter G. A. Leonard Chem. Br. 1993 29 484 487
43. F. Seela K. Xu Org. Biomol. Chem. 2008 6 3552 3560
44. G. Mdza J. Wierzchowski B. Kierdaszuk D. Shugar Bioorg. Med. Chem. 2009 17 2585 2591
45. Y. Chiang A. J. Kresge Org. Biomol. Chem. 2004 2 1090 1092
46. S. Acharya J. Barman P. Cheruku S. Chatterjee P. Acharya J. Isaksson J. Chattopadhyaya J. Am. Chem. Soc. 2004 126 8674 8681
47. S. Lohmann L. Lehmann K. Tabiti Biochemica 2000 23 28
48. A. Okamoto K. Tanaka T. Fukuta I. Saito J. Am. Chem. Soc. 2003 125 9296 9297
49. L. Bethge D. V. Jarikote O. Seitz Bioorg. Med. Chem. 2008 16 114 125
50. A. Okamoto K. Tainaka Y. Ochi K. Kanatani I. Saito Mol. BioSyst. 2006 2 122 127
51. A. Okamoto K. Kanatani I. Saito J. Am. Chem. Soc. 2004 126 4820 4827
52. F. Seela H. Xiong P. Leonard S. Budow Org. Biomol. Chem. 2009 7 1374 1387
53. R. Käppi Z. Kazimierczuk P. Järvinen F. Seela H. Lönnberg J. Chem. Soc. Perkin Trans. 2 1991 595 600
54. M. Hoffer Chem. Ber. 1960 93 2777 2781
55. V. Rolland M. Kotera J. Lhomme Synth. Commun. 1997 27 3505 3511