Bioorganic & Medicinal Chemistry 2011-06-15

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases.

Shogo Noguchi, Shintaro Takemoto, Shun-ichi Kidokoro, Kazunori Yamamoto, Masaru Hashimoto, Shogo Noguchi, Shintaro Takemoto, Shun-ichi Kidokoro, Kazunori Yamamoto, Masaru Hashimoto

Index: Bioorg. Med. Chem. 19 , 3812, (2011)

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Abstract

Cellotriose and cellotetraose analogues carrying cyclohexene rings were developed as molecular probes which are expected to mimic the transition state conformation of hydrolysis by cellulases. The cyclohexene ring was placed at the pyranose ring being expected to locate the -1 subsite of the enzyme. In order to evaluate these probes, sulfur derivatives of cellotriose and cellotetraose were also synthesized as the enzyme tolerant analogues which mimic the stable conformations of the natural cellulose. The binding assays using differential scanning calorimetry revealed that introduction of the cyclohexene ring is effective to the complexation with an endoglucanase, NCE5 from Humicola insolens.Copyright © 2011 Elsevier Ltd. All rights reserved.