Synthesis of Novel Thioglycoside Analogs as the Substrates and/or the Inhibitors of Cellobiohydrolases

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  • Terauchi Takeshi
    Biomolecular Engineering Laboratory, National Food Research Institute, NARO
  • Koyama Yoshiyuki
    Enzymology and Molecular Biology Laboratory, Department of Agricultural and Biological Chemistry, Nihon University
  • Machida Sachiko
    Biomolecular Engineering Laboratory, National Food Research Institute, NARO
  • Kasumi Takafumi
    Enzymology and Molecular Biology Laboratory, Department of Agricultural and Biological Chemistry, Nihon University
  • Komba Shiro
    Biomolecular Engineering Laboratory, National Food Research Institute, NARO

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Abstract

A series of β-(1→4)-thiooligosaccharide analogs, O-β-D-glucopyranosyl-(1→4)-S-β-D- glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (1: Glc-O-Glc-S-Glc), S-β-D-glucopyranosyl- (1→4)-O-(4-deoxy-4-thio-β-D-glucopyranosyl)-(1→4)-D-glucopyranose (2: Glc-S-Glc-O-Glc), S-β-D-glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (3: Glc-S-Glc), O-β-D-galactopyranosyl-(1→4)-S-β-D-glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (4: Gal-O-Glc-S-Glc) and O-β-D-glucopyranosyl-(1→4)-S-β-D-glucopyranosyl-(1→4)-O- (4-deoxy-4-thio-β-D-glucopyranosyl)-(1→4)-D-glucopyranose (5: Glc-O-Glc-S-Glc-O-Glc), including novel compounds were synthesized for the substrates and/or the inhibitors of cellobiohydrolases for the evaluation of cellulolytic activities. The triflated acceptors were constructed in two reaction steps, regioselective benzoylation and triflation. After S-glycosylation of these triflated acceptors, acyl protecting group was deprotected to yield target compounds. In this way, all target compounds were successfully synthesized in short-step (four reaction steps).

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