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Acta Phys. -Chim. Sin.  2005, Vol. 21 Issue (09): 952-956    DOI: 10.3866/PKU.WHXB20050902
Explore the Effect Induced by Water in the Proton Transfer Process of 5-fluorouracil
HU Xing-bang; LI Hao-ran; LIANG Wan-chun; HAN Shi-jun
Department of Chemistry, Zhejiang University, Hangzhou 310027
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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.

Key wordsDensity functional theory      5-fluorouracil      Proton transfer      Tautomerism      Water     
Received: 03 December 2004      Published: 15 September 2005
Corresponding Authors: LI Hao-ran     E-mail: lihr@zju. edu. cn
Cite this article:

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. Acta Phys. -Chim. Sin., 2005, 21(09): 952-956.

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