Lu Huiling, Drelich Audrey, Omri Mehdi, Pezron Isabelle, Wadouachi Anne, Pourceau Gwladys
TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France.
LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France.
Molecules. 2016 Sep 28;21(10):1301. doi: 10.3390/molecules21101301.
Large quantities (>3 g) of a new series of alkyl uronates were synthesized in two steps from commercial methyl hexopyranosides. Firstly, several tens of grams of free methyl α-d-glucopyranoside were selectively and quantitatively oxidized into corresponding sodium uronate using 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO)-catalyzed oxidation. Hydrophobic chains of different length were then introduced by acid-mediated esterification with fatty alcohols (ethyl to lauryl alcohol) leading to the desired alkyl glucuronates with moderate to good yields (49%-72%). The methodology was successfully applied to methyl α-d-mannopyranoside and methyl β-d-galactopyranoside. Physicochemical properties, such as critical micelle concentration (CMC), equilibrium surface tension at CMC (γ), solubility, and Krafft temperature were measured, and the effect of structural modifications on surface active properties and micelle formation was discussed.
以市售甲基己吡喃糖苷为原料，分两步合成了大量（>3 g）的一系列新型烷基糖醛酸盐。首先，使用2,2,6,6-四甲基-1-哌啶氧基自由基（TEMPO）催化氧化，将几十克游离甲基α-d-吡喃葡萄糖苷选择性地定量氧化为相应的糖醛酸钠。然后通过与脂肪醇（从乙醇到月桂醇）进行酸介导的酯化反应引入不同长度的疏水链，从而以中等到良好的产率（49%-72%）得到所需的烷基葡萄糖醛酸盐。该方法成功应用于甲基α-d-甘露吡喃糖苷和甲基β-d-半乳糖吡喃糖苷。测定了临界胶束浓度（CMC）、CMC时的平衡表面张力（γ）、溶解度和克拉夫特温度等物理化学性质，并讨论了结构修饰对表面活性性质和胶束形成的影响。
