College of Chemistry, Chongqing Normal University, Chongqing 400047, China.
Int J Biol Macromol. 2009 Nov 1;45(4):381-3. doi: 10.1016/j.ijbiomac.2009.07.002. Epub 2009 Jul 25.
The synthesis of 4-methylumbelliferyl (UMB)-penta-N-acetylchitopentaoside 4 and its inhibition effect on chitinase are described. The fluorophore-assisted carbohydrate electrophoresis (FACE) analysis showed that the partially N-acetylated chitooligosaccharide (COS) mixture mainly contained glucosamine (GlcN) and oligomers [(GlcN)n, n=2-7]. The peracetylated COSs [(GlcNAc)(n), n=1-7] were synthesized by treating the partially N-acetylated COS mixture with Ac2O-NaOAc. The peracetylated chitopentaoside 1 was obtained by isolation of peracetylated COS mixture. The peracetylated UMB chitopentaoside 3 was synthesized by treating compound 1 with 4-methylumbelliferone and a Lewis acid (SnCl4) catalyst. NaOMe in dry methanol was used for deacetylation of the blocked derivative, to give the target compound 4 in an overall yield of 32%. In binding chitinase assay, it indicates that compound 4 is much more stable than the corresponding penta-N-acetylchitopentaose 2.
描述了 4-甲基伞形酮基（UMB）-五-N-乙酰壳五糖苷 4 的合成及其对几丁质酶的抑制作用。荧光辅助碳水化合物电泳（FACE）分析表明，部分 N-乙酰化壳寡糖（COS）混合物主要含有葡萄糖胺（GlcN）和低聚物[（GlcN）n，n=2-7]。通过用 Ac2O-NaOAc 处理部分 N-乙酰化 COS 混合物，合成了全乙酰化的 COS[（GlcNAc）（n），n=1-7]。通过分离全乙酰化的 COS 混合物得到全乙酰化壳五糖苷 1。通过用 4-甲基伞形酮和路易斯酸（SnCl4）催化剂处理化合物 1，合成了全乙酰化 UMB 壳五糖苷 3。在封闭衍生物的脱乙酰化中，使用甲醇中的 NaOMe，以 32%的总收率得到目标化合物 4。在结合几丁质酶的测定中，表明化合物 4 比相应的五-N-乙酰壳五糖苷 2 更稳定。
