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. Author manuscript; available in PMC: 2019 May 20.
Published in final edited form as: Free Radic Biol Med. 2018 Mar 11;120:89–101. doi: 10.1016/j.freeradbiomed.2018.03.010

Scheme 2.

Scheme 2

Proposed mechanism of hydroxyl radical-induced DPC formation between thymidine in DNA and tyrosine residue in proteins. Hydroxyl radicals abstract a hydrogen from the 5-methyl position of thymidine to yield a reactive thymidine radical (1), which undergoes a one-electron addition to the 3-position of a tyrosine to yield a stable methylene linkage. Subsequent hydrogen abstraction from the 3-position of tyrosine (2) rearomatizes the phenol ring to yield the stable DNA-protein cross-link (3).