Synthesis, protein-binding ability and phytoalexin-elicitor activity of epoxyalkyl (1→3)-β-D-oligoglucosides

Abstract

We describe a approach for the synthesis of (1→3)-β-D-oligosaccharide derivatives 10–18. 1–9 were synthesized by treating peracetylated (1→3)-β-D-oligosaccharides with the corresponding alkenyl alcohols and Lewis acid (SnCl₄) 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 IC₅₀ 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)-β-D- oligoglucoside derivatives in eliciting phytoalexin accumulation in soybean cotyledon tissue, and 16 was kept longer time than (1→3)-β-D-glucohexaose, which indicated 16 is much more stable than (1→3)-β-D-glucohexaose. Published in 2004.