Mild generation of 5-(2'-deoxyuridinyl)methyl radical from a phenyl selenide precursor.
[reaction: see text] 5-(2'-Deoxyuridinyl)methyl radical (1) resulting from formal hydrogen atom abstraction from the methyl group of thymidine is produced from the respective phenyl selenide precursor (2) via 350 nm photolysis or mild thermolysis (37 degrees C in the presence of glutathione) under aerobic or anaerobic conditions. The mild thermal generation of a nucleoside radical provides an alternative to previously reported photochemical methods, which are not always compatible with nucleic acids.
Hong
In Seok
IS
Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Baltimore, Maryland 21218, USA.
Greenberg
Marc M
MM
D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D010777:Photochemistry
C510308:5-(2'-deoxyuridinyl)methyl; D005609:Free Radicals; D016566:Organoselenium Compounds; D003857:Deoxyuridine