S-Linked Thiomimetics of Phytoalexin-Elicitor-Active, Branched Oligosaccharides, Their Synthesis, Protein-Binding Ability and Phytoalexin-Inducing Activity

✍ Scribed by Yili Ding; Marie-Odile Contour-Galcera; Jürgen Ebel; Carmen Ortiz-Mellet; Jacques Defaye

• Book ID: 101279141
• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 379 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199905)1999:5<1143::aid-ejoc1143>3.0.co;2-u

✦ Synopsis

A further reaction, involving the sodium salt of the peracetylated β-isomeric pentathiohexa-and hexathioheptasaccharides 12,34 and 28,39, respectively, were all found to be active in 1-thio derivative of 12 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6iodo-β-D-glucopyranose ( 26), afforded the homologous eliciting phytoalexin accumulation in soybean cotyledon tissue and in binding to a glucan-binding protein of soybean, sulfur-linked hexathioheptasaccharide 3 II ,3 V -di-β-D-glucopyranosylthiogentiopentaose (28). Related sulfur-linked although to a lesser extent than the corresponding O-oligosaccharides, the alternate thiohexa-and thiohepta-positional isomers 3 II ,3 IV -di-D-β-glucopyranosylthiogentiotetraose (34) and 3 III ,3 V -di-β-D-glucopyranosylthiogentio-saccharides 12,28 being more active as compared to the geminally branched isomers 34,39. pentaose (39) have been prepared using analogous synthetic strategies. Thus, S N 2 displacement of the iodine atom in 10 S-linked thio analogs of oligosaccharins might be expected