Huang Gang-Liang, Liu Man-Xi, Mei Xin-Ya, Cao Yuan-Cheng
School of Life Science and Technology, Huazhong University of Science and Technology (East Campus), 1037 Luoyu Lu, Wuhan, 430074, China.
Glycoconj J. 2004;20(7-8):427-33. doi: 10.1023/B:GLYC.0000038289.48502.0a.
We describe a approach for the synthesis of (1-->3)-beta-D-oligosaccharide derivatives 10-18. 1-9 were synthesized by treating peracetylated (1-->3)-beta-D-oligosaccharides with the corresponding alkenyl alcohols and Lewis acid (SnCl(4)) catalyst. Epoxidation of the corresponding alkenyl oligoglucosides took place by m-CPBA. NaOMe in dry methanol was used for the deacetylation of the blocked derivatives, to give 10-18 in an overall yields of 25-32%. In subsequent glucan-binding protein of soybean assays, we found that 16 was most active, with an IC(50) value of 9 mM. However, the activities of 17, 18, 13, 14, 15, 10, 11, and 12 were gradually decreased. At the same time, we found 16 was most active as compared to the other (1-->3)-beta-D- oligoglucoside derivatives in eliciting phytoalexin accumulation in soybean cotyledon tissue, and 16 was kept longer time than (1-->3)-beta-D-glucohexaose, which indicated 16 is much more stable than (1-->3)-beta-D-glucohexaose.
我们描述了一种合成(1→3)-β-D-寡糖衍生物10 - 18的方法。通过用相应的链烯醇和路易斯酸（SnCl₄）催化剂处理全乙酰化的(1→3)-β-D-寡糖来合成1 - 9。相应的链烯基寡葡糖苷通过间氯过氧苯甲酸进行环氧化。在干燥甲醇中使用NaOMe对封闭的衍生物进行脱乙酰化，以25 - 32%的总收率得到10 - 18。在随后的大豆葡聚糖结合蛋白测定中，我们发现16活性最高，IC₅₀值为9 mM。然而，17、18、13、14、15、10、11和12的活性逐渐降低。同时，我们发现与其他(1→3)-β-D-寡葡糖苷衍生物相比，16在引发大豆子叶组织中植保素积累方面活性最高，并且16比(1→3)-β-D-葡萄糖六糖保持的时间更长，这表明16比(1→3)-β-D-葡萄糖六糖更稳定。
