Yibin Wang1, Shuo Liu2, Zechao Lin1, Yukai Fan1, Yinsheng Wang2, Xiaohua Peng1. 1. Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States. 2. Department of Chemistry, University of California Riverside , 501 Big Springs Road, Riverside, California 92521-0403, United States.
Abstract
UV irradiation of several aryl boronates efficiently produced bifunctional benzyl cations that selectively form guanine-cytosine cross-links in DNA. Photoinduced homolysis of the C-Br bond took place with the aryl boronate bromides 3a and 4a, generating free radicals that were oxidized to benzyl cations via electron transfer. However, photoirradiation of the quaternary ammonium salts 3b and 4b led to heterolysis of C-N bond, directly producing benzyl cations. The electron-donating group in the aromatic ring greatly enhanced cross-linking efficiency.
UV irradiation of several n class="Chemical">aryl boronates efficiently produced bifunctional benzyl cations that selectively form guanine-cytosine cross-links in DNA. Photoinduced homolysis of the C-Br bond took place with the aryl boronate bromides 3a and 4a, generating free radicals that were oxidized to benzyl cations via electron transfer. However, photoirradiation of the quaternary ammonium salts 3b and 4b led to heterolysis of C-N bond, directly producing benzyl cations. The electron-donating group in the aromatic ring greatly enhanced cross-linking efficiency.
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