REACTIVITY TOWARD SINGLET OXYGEN OF A 7,8-DIHYDRO-8-OXOGUANOSINE (8-HYDROXYGUANOSINE) FORMED BY PHOTOOXIDATION OF A GUANOSINE DERIVATIVE

被引:126
作者
SHEU, C [1 ]
FOOTE, CS [1 ]
机构
[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024
关键词
D O I
10.1021/ja00129a004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total quenching (k(r) + k(q)) and chemical reaction rates (k(r)) for the removal of singlet oxygen by 2,3',5'-tris((tert-butyldimethylsilyl)oxy)guanos (1) and its oxidation product, 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-7,8-dihydro-8-oxoguanosine (2), were determined by the time-resolved infrared luminescence technique and competition experiments, respectively. Compound 2 is two orders of magnitude more reactive with singlet oxygen than 1. A mechanism for the formation of 2 from 1 with singlet oxygen is proposed.
引用
收藏
页码:6439 / 6442
页数:4
相关论文
共 32 条
  • [1] Stich H.F., Karim J., Koropatnick J., Lo L., Nature, 260, pp. 722-724, (1976)
  • [2] Kasai H., Nishimura S., Nucleic Acids Res., 12, pp. 2137-2145, (1984)
  • [3] Dizdaroglu M., Biochemistry, 24, pp. 4476-4481, (1985)
  • [4] Epe B., Mutzel P., Adam W., Chem.-Biol. Interact., 67, pp. 149-165, (1988)
  • [5] Floyd R.A., West M.S., Eneff K.L., Hogsett W.E., Tingey D.T., Arch. Biochem. Biophys., (1988)
  • [6] Matsugo S., Kumaki S., Shimasaki C., Mori T., Saito I., Chem. Lett., pp. 453-456, (1993)
  • [7] Cho B.P., Kadlubar F.F., Culp S.J., Evans F.E., Chem. Res. Toxicol., 3, pp. 445-452, (1990)
  • [8] Culp S.J., Cho B.P., Kadlubar F.F., Evans F.E., Chem. Res. Toxicol., 2, pp. 416-422, (1989)
  • [9] Holmes R.E., Robins R.K., J. Am. Chem. Soc., 87, pp. 1772-1776, (1965)
  • [10] Oda Y., Uesugi S., Ikehara M., Nishimura S., Kawase Y., Ishikawa H., Inoue H., Ohtsuka E., Nucleic Acids Res., 19, pp. 1407-1412, (1991)