Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils. Catalysis by nicotine and trimethylamine.

@article{Masuda2001ChlorinationOG,
  title={Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils. Catalysis by nicotine and trimethylamine.},
  author={Mitsuharu Masuda and Tsutomu Suzuki and Marlin D. Friesen and Jean Luc Ravanat and Jean Cadet and Brigitte Pignatelli and Hoyoku Nishino and Hiroshi Ohshima},
  journal={The Journal of biological chemistry},
  year={2001},
  volume={276 44},
  pages={40486-96}
}
Activated human neutrophils secrete myeloperoxidase, which generates HOCl from H2O2 and Cl(-). We have found that various (2'-deoxy)nucleosides react with HOCl to form chlorinated (2'-deoxy)nucleosides, including novel 8-chloro(2'-deoxy)guanosine, 5-chloro(2'-deoxy)cytidine, and 8-chloro(2'-deoxy)adenosine formed in yields of 1.6, 1.6, and 0.2%, respectively, when 0.5 mM nucleoside reacted with 0.5 mM HOCl at pH 7.4. The relative chlorination, oxidation, and nitration activities of HOCl… CONTINUE READING
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