Radiolytic cyclization of stem-and-loop structured oligodeoxynucleotide with neighboring arrangement of α,ω-bis-disulfides

Organic and Biomolecular Chemistry

Volumn 8, Issue 21, 2010, Pages 4837-4842

  Tanabe, Kazuhito ^a   Matsumoto, Eiji ^a   Ito, Takeo ^a   Nishimoto, Sei Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; AQUEOUS SOLUTIONS; BINDING ACTIVITIES; CHAIN REACTION; DISULFIDE BONDS; DISULFIDE EXCHANGE; HIGH THERMAL STABILITY; HYDROGEN ATOMS; INTRAMOLECULAR EXCHANGE; LOOP STRUCTURE; MECHANISTIC STUDIES; NUCLEAR FACTORS; OLIGODEOXYNUCLEOTIDES; RADIOLYTIC METHODS; THIYL RADICALS; TRANSCRIPTIONAL FACTORS; X RAY IRRADIATION;

HYDROGEN; RADIATION CHEMISTRY; RADIOLYSIS; REACTION INTERMEDIATES; SOLUTIONS; SULFUR COMPOUNDS;

CYCLIZATION;

DISULFIDE; OLIGODEOXYRIBONUCLEOTIDE;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; X RAY;

CYCLIZATION; DISULFIDES; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; X-RAYS;

EID: 77957918630     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00275e     Document Type: Article

References (53)

1. W. Saenger, Principles of Nucleic Acid Structure, Springer-Verlag, New York, 1984
2. R. R. Sinden, DNA Structure and Function, Academic Press, New York, 1994
3. N. R. Cozzarelli, J. C. Wang, DNA Topology and Its Biological Effects, Cold Spring Harbor Laboratory Press, New York, 1990
4. G. N. Parkinson M. P. H. Lee S. Neidle Nature 2002 417 876 880
5. S. M. Gowan J. R. Harrison L. Patterson M. Valenti M. A. Read S. Neidle L. R. Kelland Mol. Pharmacol. 2002 61 1154 1162
6. M. A. Read R. J. Harrison B. Romagnoli F. A. Tanious S. Gowan A. P. Reszka W. D. Wilson L. R. Kelland S. Neidle Proc. Natl. Acad. Sci. U. S. A. 2001 98 4844 4849
7. M. Nakane S. Ichikawa A. Matsuda J. Org. Chem. 2008 73 1842 1851
8. T. Hosoya H. Takeuchi Y. Kanesaka H. Yamakawa N. Miyano-Kurosaki K. Takai N. Yamamoto H. Takaku FEBS Lett. 1999 461 136 140
9. A. Moter U. B. Göbel J. Microbiol. Methods 2000 41 85 112
10. S. Tyagi F. R. Kramer Nat. Biotechnol. 1996 14 303 308
11. S. Sando E. T. Kool J. Am. Chem. Soc. 2002 124 2096 2097
12. M. N. Stojanovic P. de Prada D. W. Landry ChemBioChem 2001 2 411 415
13. Y. Yamasaki K. Yoshikawa J. Am. Chem. Soc. 1997 119 10573 10578
14. A. Ono H. Togashi Angew. Chem., Int. Ed. 2004 43 4300 4302
15. Y. Miyake H. Togashi M. Tashiro H. Yamaguchi S. Oda M. Kudo Y. Tanaka Y. Kondo R. Sawa T. Fujimoto T. Machinami A. Ono J. Am. Chem. Soc. 2006 128 2172 2173
16. E. Meggers P. L. Holland W. B. Tolman F. E. Romesberg P. G. Schultz J. Am. Chem. Soc. 2000 122 10714 10715
17. K. Tanaka A. Tengeiji T. Kato N. Toyama M. Shionoya Science 2003 299 1212 1213
18. M. Göritz R. Krämer J. Am. Chem. Soc. 2005 127 18016 18017
19. T. Ohmichi Y. Kawamoto P. Wu D. Miyoshi H. Karimata N. Sugimoto Biochemistry 2005 44 7125 7130
20. T. Ohmichi N. Nakamura K. Yasuda N. Sugimoto J. Am. Chem. Soc. 2000 122 11286 11294
21. W. Li D. Miyoshi S. Nakano N. Sugimoto Biochemistry 2003 42 11736 11744
22. R. Iwase A. Fukui A. Kobori T. Yamaoka A. Murakami Nucleic Acids Symp. Ser. 2005 49 151 152
23. L. Kröck A. Heckel Angew. Chem., Int. Ed. 2005 44 471 473
24. G. Mayer A. Heckel Angew. Chem., Int. Ed. 2006 45 4900 4921
25. H. Asanuma T. Ito T. Yoshida X. Liang M. Komiyama Angew. Chem., Int. Ed. 1999 38 2393 2395
26. K. Tanabe H. Kanezaki H. Ishii S. Nishimoto Org. Biomol. Chem. 2007 5 1242 1246
27. K. Tanabe Z. Zhang T. Ito H. Hatta S. Nishimoto Org. Biomol. Chem. 2007 5 3745 3757
28. S. E. Osborne J. Völker S. Y. Stevens K. J. Breslauer G. D. Glick J. Am. Chem. Soc. 1996 118 11993 12003
29. M. Endo T. Majima Chem. Commun. 2004 1308 1309
30. A. A. Gorodetsky J. K. Barton J. Am. Chem. Soc. 2007 129 6074 6075
31. T. Takada C. Tanaka M. Nakamura K. Yamana Bioorg. Med. Chem. Lett. 2010 20 994 996
32. S. Antonello R. Benassi G. Gavioli F. Taddei F. Maran J. Am. Chem. Soc. 2002 124 7529 7538
33. Y. Kakizawa A. Harada K. Kataoka J. Am. Chem. Soc. 1999 121 11247 11248
34. N. K. Mathur, C. K. Narang, R. E. Williams, Polymers as Aids in Organic Chemistry, Academic Press, New York, 1980
35. M. Ishiguro, SHki no Kagaku Shuushoku, Japan Scientific Societies Press, Tokyo, 1978
36. K. Tanabe E. Kuraseko Y. Yamamoto S. Nishimoto J. Am. Chem. Soc. 2008 130 6302 6303
37. T. Ihara T. Fujii M. Mukae Y. Kitamura A. Jyo J. Am. Chem. Soc. 2004 126 8880 8881
38. Z. J. Gartner R. Grubina C. T. Calderone D. R. Liu Angew. Chem., Int. Ed. 2003 42 1370 1375
39. J. L. Czlapinski T. L. Sheppard J. Am. Chem. Soc. 2001 123 8618 8619
40. Y. Xu E. T. Kool J. Am. Chem. Soc. 2000 122 9040 9041
41. K. Fujimoto S. Matsuda N. Takahashi I. Saito J. Am. Chem. Soc. 2000 122 5646 5647
42. K. Fujimoto Y. Yoshimura T. Ikemoto A. Nakazawa M. Hayashi I. Saito Chem. Commun. 2005 3177 3179
43. G. V. Buxton C. L. Greenstock W. P. Helman A. B. Ross J. Phys. Chem. Ref. Data 1988 17 513 886
44. J. W. T. Spinks, R. J. Woods, An Introduction to Radiation Chemistry, Wiley-Interscience, New York, 1990
45. G. Wenska P. Filipiak K.-D. Asmus K. Bobrowski J. Koput B. Marciniak J. Phys. Chem. B 2008 112 10045 10053
46. M. Yamaji S. Tojo K. Takehira S. Tobita M. Fujitsuka T. Majima J. Phys. Chem. A 2006 110 13487 13491
47. M. Z. Hoffman E. Hayon J. Am. Chem. Soc. 1972 94 7950 7957
48. T. Owen D. R. Ellis Radiat. Res. 1973 53 24 32
49. M. Simic M. Z. Hoffman J. Am. Chem. Soc. 1970 92 6096 6098
50. D. Gupta A. R. Knight Can. J. Chem. 1980 58 1350 1354
51. M. Bonifacic K.-D. Asmus J. Phys. Chem. 1984 88 6286 6290
52. M. Maxam W. Gilbert Proc. Natl. Acad. Sci. U. S. A. 1977 74 560 564
53. T. Maniatis, E. F. Fritsch, J. Sambrook, J., Molecular Cloning, Cold Spring Harbor Laboratory Press, Plainview, NY, 1982