4-Thiocellooligosaccharides : Their Synthesis and use as Inhibitors of Cellulases

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Abstract
Methyl 4,4′-dithio-α-cellotrioside 1, its terra- and pentasaccharide homologues 8 and 14 were conveniently synthesized by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-α-D-galactoside 6 with the respective peracetylated 1,4-dithio-, l, 4, 4′-trithio- and l, 4, 4′, 4″-tetrathiocellooligomers, in the presence of cysteamine and dimiocrythritol in N′, N″, N″-hexamethylphosphoramide. These methyl thiocellooligosaccharides were found to be excellent inhibitors of cellulases EGI and CBHII from Humicola insolens. The affinity increased strongly with an increasing number of glycosyl units in the thiooligosaccharides.