Design and chemoenzymatic synthesis of thiooligosaccharide inhibitors of 1,3:1,4-β-D-glucanases

Vincent Moreau, Josep Lluis Viladot, Eric Samain, Antoni Planas, Hugues Driguez

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A successful chemoenzymatic synthesis of oligosaccharides with an interglucosidic sulfur atom as inhibitors of 1,3:1,4-β-D-glucanases is described. The key compound 3a was synthesized from acetylated 1-thio-β-laminaribiose 4 and the methyl 4'-O-triflyl-lactoside 5. After de-O-acylation, the tetrasaccharide 3b was used as an acceptor and glucose-1-P as a donor in a phosphorolytic elongation catalysed by cellodextrin phosphorylase from Clostridium thermocellum. The expected pentasaccharide 2a and hexasaccharide 1 were isolated in 56% and 13% yield, respectively. As expected, the thiooligosaccharides 1, 2a, and 3b were resistant to enzymatic cleavage by 1,3:1,4-β-D-glucanase isolated from Bacillus licheniformis. Furthermore, they have been shown to act as competitive inhibitors of the hydrolysis of the chromophoric trisaccharide substrate 11 by this enzyme.

Idioma originalAnglès
Pàgines (de-a)1849-1855
Nombre de pàgines7
RevistaBioorganic and Medicinal Chemistry
Estat de la publicacióPublicada - de nov. 1996


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