Efficient conversion of thymine glycol into the formamide lesion in oligonucleotides

Tetrahedron Letters

Volumn 50, Issue 6, 2009, Pages 723-726

  Toga, Tatsuya ^a   Yamamoto, Junpei ^a   Iwai, Shigenori ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

DNA damage; Oligonucleotides; Periodate oxidation; Thymine glycol

Indexed keywords

FORMAMIDE; GLYCOL; N (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL) FORMAMIDE; OLIGONUCLEOTIDE; PERIODATE SODIUM; THYMINE; THYMINE 5,6 DIHYDRO 5,6 DIHYDROXYTHYMIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION;

EID: 57749092636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.001     Document Type: Article

References (28)

1. Friedberg E.C., Walker G.C., Siede W., Wood R.D., Schultz R.A., and Ellenberger T. DNA Repair and Mutagenesis. 2nd ed. (2006), ASM Press, Washington DC 25-29
2. Iwai S. Angew. Chem., Int. Ed. 39 (2000) 3874
3. Iwai S. Chem. Eur. J. 7 (2001) 4343
4. Shimizu T., Manabe K., Yoshikawa S., Kawasaki Y., and Iwai S. Nucleic Acids Res. 34 (2006) 313
5. Katafuchi A., Nakano T., Masaoka A., Terato H., Iwai S., Hanaoka F., and Ide H. J. Biol. Chem. 279 (2004) 14464
6. Kusumoto R., Masutani C., Iwai S., and Hanaoka F. Biochemistry 41 (2002) 6090
7. Ide H., Kow Y.W., and Wallace S.S. Nucleic Acids Res. 13 (1985) 8035
8. Lustig M.J., Cadet J., Boorstein R.J., and Teebor G.W. Nucleic Acids Res. 20 (1992) 4839
9. Breimer L.H., and Lindahl T. Biochemistry 24 (1985) 4018
10. Olinski R., Zastawny T., Budzbon J., Skokowski J., Zegarski W., and Dizdaroglu M. FEBS Lett. 309 (1992) 193
11. Höss A., Jaruga P., Zastawny T.H., Dizdaroglu M., and Pääbo S. Nucleic Acids Res. 24 (1996) 1304
12. Cadet J., Narin R., Voituriez L., Remin M., and Hruska F.E. Can. J. Chem. 59 (1981) 3313
13. Claridge T.D.W. High-Resolution NMR Techniques in Organic Chemistry (1999), Elsevier Science, Oxford pp 313-328
14. Paul C.R., Wallace J.C., Alderfer J.L., and Box H.C. Int. J. Radiat. Biol. 54 (1988) 403
15. Wagner J.R., Decarroz C., Berger M., and Cadet J. J. Am. Chem. Soc. 121 (1999) 4101
16. Girault I., Molko D., and Cadet J. Free Radical Res. 20 (1994) 315
17. Girault I., Fort S., Molko D., and Cadet J. Free Radical Res. 26 (1997) 257
18. Luo Y., Henle E.S., and Linn S. J. Biol. Chem. 271 (1996) 21167
19. Greene K.F., Budzinski E.E., Iijima H., Dawidzik J.B., DeFedericis H.-C., Patrzyc H.B., Evans M.S., Bailey D.T., Freund H.G., and Box H.C. Radiat. Res. 167 (2007) 146
20. Maufrais C., and Boulard Y. Can. J. Physiol. Pharmacol. 80 (2002) 609
21. Czarnik A.W., and Leonard N.J. J. Am. Chem. Soc. 104 (1982) 2624
22. Gao J., Liu H., and Kool E.T. J. Am. Chem. Soc. 126 (2004) 11826
23. Guy A., Duplaa A.-M., Ulrich J., and Téoule R. Nucleic Acids Res. 19 (1991) 5815
24. Guy A., Dubet J., and Téoule R. Tetrahedron Lett. 34 (1993) 8101
25. Gasparutto D., Ait-Abbas M., Jaquinod M., Boiteux S., and Cadet J. Chem. Res. Toxicol. 13 (2000) 575
26. Sugiyama H., Matsuda S., Kino K., Zhang Q.-M., Yonei S., and Saito I. Tetrahedron Lett. 37 (1996) 9067
27. Shishkina I.G., and Johnson F. Chem. Res. Toxicol. 13 (2000) 907
28. Karino N., Ueno Y., and Matsuda A. Nucleic Acids Res. 29 (2001) 2456