|Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥1,200,000 (Direct Cost: ¥1,200,000)
Synthesis of 6-O-substituted guaiacyl and p-nitrophenyl glucosides together with p-nitrophenyl 6.6'-di-O-methyl-cellobioside were attempted. A route consisting of tosylation of 6-OH and protection of other hydroxyl groups with vinylethyl ether followed by substitution of tosyl groups by various alkoxy anions was adopted for the synthesis of these cellulose model compounds. Thus, 6-O-methyl-, 6-O-ethyl-, 6-O-butyl-, and 6-O-isobutyl-derivatives of guaiacyl glucoside were obtained successfully after removal of ethoxyethyl substituents with acetic acid, whereas those of p-nitrophenyl glucoside could not be synthesized by this procedure. Then, these synthesized compounds were subjected to cellulase treatment in order to examine the influence of substituents at the 6-positon toward enzymatic hydrolysis. Two methods, high pressure liquid chromatography and DELTA epsilon method, were checked to measure the amount of phenols produced from aryl glucosides or the degree of hydrolysis, and the latter was found to be usable. The resistance to hydrolysis of glucosidic bonds caused by introduction of a substituent at 6-position is still under measurement. On the other hand, a study on the distribution of methyl groups along a cellulose chain by the use of enzymatic hydrolysis was completed. This revealed that commercial methyl cellulose are substituted heterogeneously along a cellulose chain, but more homogeneously than that prepared by the use of nonaqueous cellulose solvent, powdered sodium hydroxide and methyl iodide.