Organic Letters
Organic Letters
5 years ago

Independent Photochemical Generation and Reactivity of Nitrogen-Centered Purine Nucleoside Radicals from Hydrazines

Independent Photochemical Generation and Reactivity of Nitrogen-Centered Purine Nucleoside Radicals from Hydrazines
Liwei Zheng, Michael D. Sevilla, Marc M. Greenberg, Lu Lin, Amitava Adhikary, Ke Qu
Photochemical precursors that produce dA• and dG(N2–H)• are needed to investigate their reactivity. The synthesis of two 1,1-diphenylhydrazines (1, 2) and their use as photochemical sources of dA• and dG(N2–H)• is presented. Trapping studies indicate production of these radicals with good fidelity, and 1 was incorporated into an oligonucleotide via solid-phase synthesis. Cyclic voltammetric studies show that reduction potentials of 1 and 2 are lower than those of widely used “hole sinks”, e.g., 8-oxodGuo and 7-deazadGuo, to investigate DNA–hole transfer processes. These molecules could be useful (a) as sources of dA• and dG(N2–H)• at specific sites in oligonucleotides and (b) as “hole sinks” for the study of DNA–hole transfer processes.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03368

DOI: 10.1021/acs.orglett.7b03368

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