DNA alkylation promoted by an electron-rich quinone methide intermediate

作     者：Chengyun Huang Steven E. Rokita 

作者机构：Department of Chemistry and Biochemistry University of Maryland College Park MD 20742 USA Sichuan Institute of Geological Engineering Investigation Chengdu 610072 China Department of Chemistry Johns Hopkins University Baltimore MD 21218 USA 

出 版 物：《Frontiers of Chemical Science and Engineering》 (化学科学与工程前沿（英文版）)

年 卷 期：2016年第10卷第2期

页      面：213-221页

核心收录：

学科分类：0710[理学-生物学] 071010[理学-生物化学与分子生物学] 081702[工学-化学工艺] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 

基　　金：the NIH for partial support of this project 

主　　题：quione methide DNA alkylation reversible covalent reaction bioconjugation target-directed modification of nucleic acids 

摘      要：Biological application of conjugates derived from oligonucleotides and quinone methides have pre- viously been limited by the slow exchange of their covalent self-adducts and subsequent alkylation of target nucleic acids. To enhance the rates of these processes, a new quinone methide precursor with an electron donating substituent has been prepared. Additionally, this substi- tuent has been placed para to the nascent exo-methylene group of the quinone methide for maximum effect. A conjugate made from this precursor and a 5＇-aminohex- yloligonucleotide accelerates formation of its reversible self-adduct and alkylation of its complementary DNA as predicted from prior model studies.