Efficient C2′α-hydroxylation of deoxyribose in protein-induced Z-form DNA

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1526-1531

  Oyoshi, Takanori ^a   Kawai, Kiyohiko ^a,b   Sugiyama, Hiroshi ^a  

^a Tokyo Medical and Dental University ^*  (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; GENES; HYDROXYLATION; PHOTOCHEMICAL FORMING; PHOTOREACTIVITY; RNA;

OLIGONUCLEOTIDES;

PROTEINS;

ADENOSINE DEAMINASE; CYTOSINE; DEOXYRIBOSE; GUANINE; METHYL GROUP; OLIGONUCLEOTIDE; RIBONUCLEASE; SODIUM CHLORIDE; URACIL DERIVATIVE; 5-IODOURACIL; DNA; DNA BINDING PROTEIN; DRUG DERIVATIVE; DSRNA ADENOSINE DEAMINASE; IODOURACIL; RIBONUCLEASE T1; URACIL;

ARTICLE; CHEMICAL BINDING; CONFORMATIONAL TRANSITION; DNA BINDING; DNA CONFORMATION; DNA STRUCTURE; HYDROXYLATION; MOLECULAR STABILITY; PHOTOREACTIVITY; PROTEIN DNA INTERACTION; STEREOSPECIFICITY; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; METABOLISM; PHOTOCHEMISTRY; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM; SYNTHESIS;

ADENOSINE DEAMINASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DEOXYRIBOSE; DNA; DNA-BINDING PROTEINS; HUMANS; HYDROXYLATION; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; PHOTOCHEMISTRY; PROTEIN STRUCTURE, TERTIARY; RIBONUCLEASE T1; STEREOISOMERISM; SUBSTRATE SPECIFICITY; URACIL;

EID: 0037433033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028388g     Document Type: Article

References (41)

1. Cozzarelli, N. R.; Wang, J. C. DNA Topology and Its Biological Effects; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1990.
2. (a) Sinden, R. R. DNA Strucutre and Function; Academic Press: New York, 1994.
3. (b) Travers, A. A. Annu. Rev Biochem. 1989, 58, 427.
4. (a) Chen, T.; Cook, G. P.; Koppisch, A. T.; Greenberg, M. M. J. Am. Chem. Soc. 2000, 122, 3861.
5. (b) Cook, G. P.; Greenberg, M. M. J. Am. Chem. Soc. 1996, 118, 10025.
6. (c) Cook, G. P.; Chen, T.; Koppisch, A. T.; Greenberg, M. M. J. Am. Chem. Soc. 1999, 121, 451.
7. (a) Sugiyama, H.; Tsusumi, Y.; Saito, I. J. Am. Chem. Soc. 1990, 112, 6720.
8. (b) Sugiyama, H.; Tsutsumi, Y.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1993, 115, 4443.
9. (c) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
10. (d) Kawai, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1999, 121, 1391.
11. (e) Sugiyama, H.; Fujimoto, K.; Saito, I. Tetrahedron Lett. 1997, 38, 8057.
12. (f) Kawai, K.; Saito, I.; Kawashima, E.; Ishido, R.; Sugiyama, H. Tetrahedron Lett. 1999, 40, 2589.
13. (g) Oyoshi, T.; Wang, A. H.-J.; Sugiyama, H. J. Am. Chem. Soc. 2002, 124, 2086.
14. (h) Kawai, K.; Saito, I.; Sugiyama, H. Tetrahedron Lett. 1999, 40, 5721.
15. (a) Wolfl, S.; Martines, C.; Rich, A.; Majzoub, J. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3664.
16. (b) Herbert, A.; Rich, A. J. Biol. Chem. 1996, 271, 11595.
17. (c) Liu, R.; Liu, H.; Chen, X.; Kirby, M.; Brown, P. O.; Zhao, K. Cell 2001, 106, 309.
18. Zacharias, W.; O'Connor, T. R.; Larson, J. E. Biochemistry 1988, 27, 2970.
19. (a) Sheridan, S. D.; Benham, C. J.; Hatfield, G. W. J. Biol. Chem. 1999, 274, 8169.
20. (b) Schroth, G. P.; Chou, P.-J.; Ho, P. S. J. Biol. Chem. 1992, 267, 11846.
21. (c) Jaworski, A. J.; Higgins, N. P.; Wells, R. D.; Zacharias, W. J. Biol. Chem. 1991, 266, 2576.
22. (a) Herbert, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12132.
23. (b) Brown, B. A., II; Lowenhaupt, K.; Wilbert, C. M.; Hanlon, E. B.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13532.
24. (c) Schade, M.; Turner, C. J.; Kuhne, R.; Schmieder, P.; Lowenhaupt, K.; Herbert, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12465.
25. (d) Herbert, A. G.; Spitzner, J. R.; Lowenhaupt, K.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 3339.
26. (e) Herbert, A.; Spitner, J.; Lowenhaupt, K.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7550.
27. (f) Schwartz, T.; Rould, M. A.; Lowenhaupt, K.; Herbert, A.; Rich, A. Science 1999, 284, 1841.
28. Schwartz, T.; Behlke, J.; Lowenhaupt, K.; Heinemann, U.; Rich, A. Nat. Struct. Biol. 2001, 8, 761.
29. (a) Sugiyama, H.; Kawai, K.; Matsunaga, A.; Fujimoto, K.; Saito, I.; Robinson, H.; Wang, A. H.-J. Nucleic Acids Res. 1996, 24, 1272.
30. (b) Van Liar, J. J. C.; Smits, M. T.; Buck, H. M. Eur. J. Biochem. 1983, 132, 55.
31. Berger, I.; Willam, W.; Manoharan, R.; Schwartz, T.; Alfken, J.; Kim, Y.-G.; Lowenhaupt, K.; Herbert, A.; Rich, A. Biochemistry 1998, 37, 13313.
32. (a) Kim, Y.-G.; Kim, P. S.; Herbert, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12875.
33. (b) Johnston, B. H.; Rich, A. Cell 1985, 42, 713.
34. (c) Barton, J. K. Science 1986, 233, 727.
35. (d) Nordheim, A.; Pardue, M. L.; Lafer, E. M.; Moller, A.; Stollar, B. D.; Rich, A. Nature 1981, 294, 417.
36. (a) Herbert, A.; Rich, A. Nucleic Acids Res. 1993, 21, 2669.
37. (b) Herbert, A.; Alfken, J.; Kim, Y.-G.; Mian, I. S.; Nishikura, K.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 8421.
38. (d) Herbert, A.; Schade, M.; Lowenhaupt, K.; Alfken, J.; Schwartz, T.; Shlyakhtenko, L. S.; Lyubchenko, Y. L.; Rich, A. Nucleic Acids Res. 1998, 26, 3486.
39. Herbert, A.; Alfken, J.; Kim, Y.-G.; Mian, I. S.; Nishikura, K.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 8421.
40. (a) Wagenknecht, H.-A.; Rajski, A. R.; Pascaly, M.; Stemp, E. D. A.; Barton, J. K. J. Am. Chem. Soc. 2001, 123, 4400.
41. (b) Rajski, S. R.; Barton, J. K. Biochemistry 2001, 40, 5556.