オリゴサッカリンの化学合成 : ファイトアレキシンエリシターについて

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In this article are described the synthetic studies on two types of “oligosaccharins”, oligosaccharides from both fungal and plant origins, that elicit phytoalexin accumulation in soybean.<BR>Two research groups have synthesized oligosaccharides related to β-glucan elicitor derived from pathogenic fungal cell wall.<BR>Biological examination of the chemically synthesized oligo-β-glucosides revealed that minimum structure required for the elicitor activity is β-D-glucohexaoside, and that the branched trisaccharide at nonreducing end of the oligoglucosides is essential for maximum elicitor activity.<BR>α- (1→4) -Linked oligogalacturonic acids (d.p. 10-13) derived from plant cell wall pectic polysaccharides are the “endogeneous elicitors” of phytoalexin accumulation in soybean.<BR>Total synthesis of dodecagalacturonic acid was achieved by way of highly stereoselective glycosylation that involved glycosyl fluorides as the donors and oxidation of the twelve primary hydroxy groups in the α- (1→4) -linked galactododecaoside derivative. The synthetic dodecagalacturonic acid was active as an elicitor of soybean phytoalexin and was synergistic with the hepta-β-glucoside elicitor.
社団法人有機合成化学協会の論文