Huang G
College of Chemistry, Chongqing Normal University, Chongqing, China.
J Enzyme Inhib Med Chem. 2009 Apr;24(2):453-6. doi: 10.1080/14756360802188545.
The synthesis and stability of 4-methylumbelliferyl (1 --> 3)-beta-D-pentaglucoside 3 are described. The (1 --> 3)-beta-D-glucan isolated from the cell walls of Saccharomyces cerevisiae was recovered from the aqueous medium as water-insoluble particles by the spray drying (GS) method. The acid-solubilized (1 --> 3)-beta-D-oligoglucosides were prepared by partial acid hydrolysis of glucan. The peracetylated (1 --> 3)-beta-D-pentaglucoside 1 was obtained by isolation of peracetylated (1 --> 3)-beta-D-oligoglucoside mixture. The peracetylated 4-methylumbelliferyl (1 --> 3)-beta-D-pentaglucoside 2 was synthesized by treating compound 1 with the 4-methylumbelliferone and a Lewis acid (SnCl4) catalyst. NaOMe in dry methanol was used for the deacetylation of the blocked derivative, to give the target compound 3 in an overall yield of 35%. Activity assays with beta-glucosidase indicated that compound 3 was much more stable than the corresponding pentasaccharide.
描述了4-甲基伞形酮基（1→3）-β-D-五葡糖苷3的合成与稳定性。从酿酒酵母细胞壁分离得到的（1→3）-β-D-葡聚糖通过喷雾干燥（GS）法从水介质中回收为水不溶性颗粒。酸溶性（1→3）-β-D-寡葡糖苷通过葡聚糖的部分酸水解制备。通过分离全乙酰化的（1→3）-β-D-寡葡糖苷混合物得到全乙酰化的（1→3）-β-D-五葡糖苷1。全乙酰化的4-甲基伞形酮基（1→3）-β-D-五葡糖苷2通过用4-甲基伞形酮和路易斯酸（SnCl4）催化剂处理化合物1合成。干燥甲醇中的NaOMe用于对封闭衍生物进行脱乙酰化，以35%的总收率得到目标化合物3。用β-葡萄糖苷酶进行的活性测定表明，化合物3比相应的五糖稳定得多。
