Photochemical Generation of Benzyl Cations That Selectively Cross-Link Guanine and Cytosine in DNA

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• 作者：Yibin Wang ; Shuo Liu ; Zechao Lin ; Yukai Fan ; Yinsheng Wang ; Xiaohua Peng
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：18
• 期：11
• 页码：2544-2547
• 全文大小：326K
• 年卷期：0
• ISSN：1523-7052

文摘

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.