通过在二元溶剂混合物中高区域选择性酶酰化作用高效合成 1-β-D-阿拉伯呋喃糖基胞嘧啶 5'-O-月桂酸酯。
Efficient synthesis of 5'-O-laurate of 1-beta-D-arabinofuranosylcytosine via highly regioselective enzymatic acylation in binary solvent mixtures.
机构信息
State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Wushan Road 381, Guangzhou 510641, China.
出版信息
Bioorg Med Chem Lett. 2010 Jul 15;20(14):4125-7. doi: 10.1016/j.bmcl.2010.05.077. Epub 2010 Jun 10.
Regioselective enzymatic acylations of 1-beta-D-arabinofuranosylcytosine (ara-C) with vinyl laurate (VL) in binary organic solvents were explored for the preparation of 5'-O-laurate of ara-C. Among the nine kinds of enzymes, Novozym 435 showed the highest regioselectivity (>99.9%) towards the 5'-OH of ara-C. This lipase showed higher catalytic activity in hexane-pyridine than in other tested solvent mixtures. The most suitable VL to ara-C molar ratio, initial water activity, and reaction temperature were shown to be 15:1, 0.07, and 50 degrees C, respectively, under which the initial reaction rate and the maximum substrate conversion were as high as 84.0 mmol L(-1) h(-1) and 98.1%, respectively. The product of Novozym 435-catalyzed acylation was characterized by (13)C NMR and confirmed to be 5'-O-laurate of ara-C.
研究了 1-β-D-阿拉伯呋喃糖基胞嘧啶（ara-C）与月桂烯酸乙烯酯（VL）在二元有机溶剂中的区域选择性酶酰化反应，以制备 5'-O-月桂酸酯的 ara-C。在 9 种酶中，Novozym 435 对 ara-C 的 5'-OH 表现出最高的区域选择性（>99.9%）。这种脂肪酶在正己烷-吡啶中的催化活性高于其他测试的溶剂混合物。结果表明，最适宜的 VL 与 ara-C 的摩尔比、初始水活度和反应温度分别为 15:1、0.07 和 50°C，在此条件下，初始反应速率和最大底物转化率分别高达 84.0mmol/L·h 和 98.1%。Novozym 435 催化酰化的产物通过（13）C NMR 进行了表征，并确认为 ara-C 的 5'-O-月桂酸酯。
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