MacFarland J G, Kirk M C, Ludlum D B
Department of Pharmacology, University of Massachusetts Medical School, Worcester 01655.
Biochem Pharmacol. 1990 Jan 1;39(1):33-6. doi: 10.1016/0006-2952(90)90645-2.
The 2-haloethylnitrosoureas have been shown to form the cross-linked structure 1-(3-cytosinyl),2-(1-guanyl)ethane in DNA. This cross-link has now been synthesized by the reaction of O6-(2-fluoroethyl)guanosine with deoxycytidine in dimethyl sulfoxide followed by removal of the sugars by acid hydrolysis. This synthetic route supports the mechanism for cross-link formation in DNA that involves an initial attack on the O6-position of guanine, followed by a rearrangement and subsequent reaction with cytosine. It also provides a practical route to the synthesis of 1-(3-cytosinyl),2-(1-guanyl)ethane for studies involving formation of this cross-link in DNA.
已证明2-卤代乙基亚硝基脲可在DNA中形成交联结构1-(3-胞嘧啶基),2-(1-鸟嘌呤基)乙烷。现在通过在二甲基亚砜中使O6-(2-氟乙基)鸟苷与脱氧胞苷反应，然后通过酸水解去除糖，合成了这种交联物。这条合成路线支持了DNA中交联形成的机制，该机制涉及对鸟嘌呤O6位的初始攻击，随后进行重排并与胞嘧啶发生后续反应。它还为合成1-(3-胞嘧啶基),2-(1-鸟嘌呤基)乙烷提供了一条实用路线，用于涉及DNA中这种交联形成的研究。
