Conformation-dependent photochemistry of 5-halouracil-containing DNA: Stereospecific 2'α-hydroxylation of deoxyribose in Z-form DNA [7]

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1391-1392

  Kawai, Kiyohiko ^a   Saito, Isao ^a   Sugiyama, Hiroshi ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DNA; DNA Z; URACIL DERIVATIVE;

DNA DETERMINATION; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; LETTER; PHOTOCHEMISTRY; PROTEIN DNA INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033576988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9827200     Document Type: Letter

References (19)

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6. Recently, Rich and colleagues have reported the creation of a Z-form-specific endonuclease as a probe for Z-DNA. (a) Kim, Y.-G.; Kim, P. S.; Herbert, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12875.
7. (b) Herbert, A.; Lowenhaupt, K.; Spitzer, J.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7550.
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10. (c) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
11. (d) Sugiyama, H.; Fujimoto, K.; Saito, I. Tetrahedron Lett. 1997, 38, 8057.
12. Johnston, B. H.; Rich, A. Cell 1985, 42, 713.
13. Sugiyama, H.; Kawai, K.; Matsunaga, A.; Fujimoto, K.; Sailo, I.; Robinson, H.; Wang, A. H.-J. Nucleic Acids Res. 1996, 24, 1272.
14. 5a Formation of these photoproducts was further confirmed by ESMS. ESMS (negative); 4: calcd 2277.5, found 2277.1. 5: calcd 2265.5, found 2264.8.
15. 1U with NaCl will be reported elesewhere.
16. ESMS (negative); 7: calcd 2428.6. found 2428.2.
17. 18O atom into the C2′-hydroxylation product.
18. The molecular basis for the preferential hydroxylation in the Z-form DNA is not fully understood; however, the structural characteristics of Z-form DNA such as C3 endo sugar puckering and alternative syn-anti conformation might effect the partitioning of the decomposition paths of hydroperoxide intermediate 8.
19. Xodo, L.-E.; Manzini, G.; Quadrifoglio, F.; van der Marel, G. A.; van Boom, J. H. Biochemistry 1988, 27, 6327.