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Photochemical Generation of Benzyl Cations That Selectively Cross-Link Guanine and Cytosine in DNA.
Wang, Yibin; Liu, Shuo; Lin, Zechao; Fan, Yukai; Wang, Yinsheng; Peng, Xiaohua.
Affiliation
  • Wang Y; Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
  • Liu S; Department of Chemistry, University of California Riverside , 501 Big Springs Road, Riverside, California 92521-0403, United States.
  • Lin Z; Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
  • Fan Y; Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
  • Wang Y; Department of Chemistry, University of California Riverside , 501 Big Springs Road, Riverside, California 92521-0403, United States.
  • Peng X; Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
Org Lett ; 18(11): 2544-7, 2016 06 03.
Article in En | MEDLINE | ID: mdl-27191599
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Benzene Derivatives / Cross-Linking Reagents / Cytosine / Guanine Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2016 Document type: Article Affiliation country: Country of publication:
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Benzene Derivatives / Cross-Linking Reagents / Cytosine / Guanine Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2016 Document type: Article Affiliation country: Country of publication: