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Selenium‐Mediated Dehalogenation of Halogenated Nucleosides and its Relevance to the DNA Repair Pathway
Author(s) -
Mondal Santanu,
Manna Debasish,
Mugesh Govindasamy
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503598
Subject(s) - halogenation , chemistry , deoxyribose , dna , uracil , dna glycosylase , ribose , moiety , nucleic acid , biochemistry , selenium , dna repair , dna synthesis , combinatorial chemistry , stereochemistry , enzyme , organic chemistry
Halogenated nucleosides can be incorporated into the newly synthesized DNA of replicating cells and therefore are commonly used in the detection of proliferating cells in living tissues. Dehalogenation of these modified nucleosides is one of the key pathways involved in DNA repair mediated by the uracil‐DNA glycosylase. Herein, we report the first example of a selenium‐mediated dehalogenation of halogenated nucleosides. We also show that the mechanism for the debromination is remarkably different from that of deiodination and that the presence of a ribose or deoxyribose moiety in the nucleosides facilitates the deiodination. The results described herein should help in understanding the metabolism of halogenated nucleosides in DNA and RNA.