Synthesis of ss-glucan oligosaccharides and their biological evaluation

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In this report, we describe the synthesis and biological evaluation of β (1,3) oligosaccharides possessing an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benziliden protecting group finctioned as an effective glycosyl acceptor for the synthesis ofβ ・1,3)linked glycosides. Using a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors permitted β ・1,3)linear octa-to hexadecasaccharides and branched nona- to heptadecasaccharides to be prepared in good total yields. Measurements of the competitive effects of oligosaccharides on the binding of a soluble dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasacccharide and the linear hexadecasacccharides 2 also have binding activity for to dectine-1. In addition, the two oligosaccharides exhibited agonist activity in a luciferase-assisted NF-kB assay. This represents the first demonstration of a purely synthetic oligosaccahrides stimulating immunity mediated by dectin-1.