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Hydrolytic Deamination Mechanisms of Guanosine Monophosphate: A Computational Study
Computational and Theoretical Chemistry ( IF 3.0 ) Pub Date : 2020-01-27 , DOI: 10.1016/j.comptc.2020.112732
Mansour H. Almatarneh , Reema A. Omeir , Saddam AL Demour , Ismael A. Elayan , Shahidul Islam , Raymond A. Poirier

The computational importance of guanosine monophosphate (GMP) comes from its importance in the synthesis of nucleic acids. Deamination reaction mechanisms, kinetics, and thermodynamics of GMP with 3H2O and 2H2O/OH to produce xanthosine monophosphate (XMP) have been investigated. The proposed reactions were optimized in the gas-phase and in an aqueous medium. Two key steps were found for the proposed pathways: a tetrahedral intermediate formation and a single water-mediated six-membered ring transition state, yielding the desired product. The deamination of GMP with 2H2O/OH yield deprotonated XMP with only one pathway, which is highly exothermic, and the activation energy is significantly lower (33 kJ mol-1 at M11/6-31G(d)) compared to the other pathways. Our results suggest that pathway C is the most kinetically and thermodynamically favorable mechanism for the deamination of GMP with 3H2O with the lowest energy barrier of 123 kJ mol-1, due to multiple functions of water that enhance the reaction profile.



中文翻译:

鸟苷一磷酸的水解脱氨机理:计算研究

鸟苷一磷酸(GMP)的计算重要性来自其在核酸合成中的重要性。脱氨反应的机制,动力学,并用3H GMP的热力学2 O和2H 2 O / OH -以产生黄苷单磷酸(XMP)进行了研究。拟议的反应在气相和水性介质中进行了优化。对于拟议的途径,发现了两个关键步骤:四面体中间体的形成和单水介导的六元环过渡态,产生了所需的产物。GMP与2H脱氨2 O / OH -屈服去质子XMP -与其他途径相比,只有一个途径是高度放热的,活化能明显较低(在M11 / 6-31G(d)处为33 kJ mol -1)。我们的结果表明,途径3 C是用3H 2 O脱氨GMP的动力学和热力学上最有利的机理,其最低能垒为123 kJ mol -1,这是由于水的多种功能增强了反应特性。

更新日期:2020-01-27
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