The Journal of organic chemistry

Trapping phosphodiester-quinone methide adducts through in situ lactonization

Q Zhou, KD Turnbull

Index: Zhou, Qibing; Turnbull, Kenneth D. Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2022 - 2029

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Citation Number: 18

Abstract

The goal of in situ modification of DNA via phosphodiester alkylation has led to our design of quinone methide derivatives capable of alkylating dialkyl phosphates. A series of catechol derivatives were investigated to trap the phosphodiester-quinone methide alkylation adduct through in situ lactonization. The catechol derivatives were uniquely capable of characterizable p-quinone methide formation for mechanistic clarity. These investigations ...