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Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2018-03-19 , DOI: 10.1016/j.bioorg.2018.03.018
M. Antonela Zígolo , Maximiliano Salinas , Laura Alché , Alicia Baldessari , Guadalupe García Liñares

We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. Moreover, in order to explain the reactivity of glycyrrhetinic acid and the acetylated derivative to different nucleophiles in the enzymatic reactions, molecular docking studies were carried out. In addition, one of the synthesized compounds exhibited remarkable antiviral activity against TK + and TK- strains of Herpes simplex virus type 1 (HSV-1), sensitive and resistant to acyclovir (ACV) treatment.



中文翻译:

化学酶法合成具有抗病毒活性的新的甘草次酸衍生物。分子对接研究

我们提出了一种合成一系列甘草次酸衍生物的有效方法。通过化学酶促反应获得了六种衍生物,其中五种是新化合物,而且收率非常好。为了找到最佳的反应条件,研究了酶源,亲核试剂:底物比例,酶:底物比例,溶剂和温度等各种参数的影响。考虑到它们的优点,例如温和的反应条件和低的环境影响,通过脂肪酶催化获得的优异结果使该方法非常有效。此外,为了解释在酶促反应中甘草次酸和乙酰化衍生物对不同亲核试剂的反应性,进行了分子对接研究。此外,

更新日期:2018-03-19
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