引用本文:
胡兴邦, 李浩然, 梁婉春, 韩世钧. 水对5-氟尿嘧啶质子转移影响规律的研究[J]. 物理化学学报,
2005, 21(09): 952-956.
doi:
10.3866/PKU.WHXB20050902
Citation: HU Xing-bang, LI Hao-ran, LIANG Wan-chun, HAN Shi-jun. Explore the Effect Induced by Water in the Proton Transfer Process of 5-fluorouracil[J]. Acta Physico-Chimica Sinica, 2005, 21(09): 952-956. doi: 10.3866/PKU.WHXB20050902
Citation: HU Xing-bang, LI Hao-ran, LIANG Wan-chun, HAN Shi-jun. Explore the Effect Induced by Water in the Proton Transfer Process of 5-fluorouracil[J]. Acta Physico-Chimica Sinica, 2005, 21(09): 952-956. doi: 10.3866/PKU.WHXB20050902
水对5-氟尿嘧啶质子转移影响规律的研究
摘要:
采用密度泛函理论(DFT)B3LYP方法, 在6-311++G(d, p)基组上研究了由质子转移引起的5-氟尿嘧啶(5-FU)的异构化反应. 共研究了38个含水与不含水的构型, 其中包括15个过渡态结构. 研究发现, 在5-氟尿嘧啶周围存在两类不同的区域, 在其中一类区域中, 水分子能促进质子转移的发生；而在另一类区域中, 水分子却能阻碍质子转移的发生. 通过与尿嘧啶质子转移过程相比较, 发现在各种情况下5-氟尿嘧啶异构化为烯醇式的几率均比尿嘧啶的大, 在一定程度上解释了为什么5-氟尿嘧啶具有优良抗癌作用的同时具有一定的毒副作用.
English
Explore the Effect Induced by Water in the Proton Transfer Process of 5-fluorouracil
Abstract:
In order to investigate the tautomerism of 5-fluorouracil (5-FU) induced by proton transfer, we describe a study of structural tautomer interconversion using density functional theory (DFT) calculations at B3LYP/6-311++G(d, p) level of the theory. Thirty-eight geometries including fifteen transition states with and without water molecule were studied. The calculated results indicate that there are two absolutely opposite regions in the vicinity of 5-FU. In one of the regions, water molecules can assist the tautomerism from 5-FU to its enol form (5-FU*), whereas in another region, water molecules can protect 5-FU from tautomerizing to 5-FU*. Furthermore, compared with the tautomerizing processes of uracil, the probability of 5-FU to tautomerize to its enol form is much higher. Based on such facts, the reason why 5-FU is an effective anticancer medicament but with some of toxicity is explained to some extent.
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