Synthesis of alternatingly 6-O-methylated cellulose via enzymatic polymerization of a substituted cellobiosyl fluoride monomer catalyzed by cellulase

Novel cellobiose derivatives, 6-O-methyl, 6′-O-methyl, 6,6′-di-O-methyl- β-cellobiosyl fluorides, have been prepared and their hydrolytic behaviour as well as polymerizability by a purified cellulase from Trichoderma viride were investigated. Among these compounds, 6-O-methyl-β-cellobiosyl fluoride...

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Bibliographic Details
Published in:Cellulose (London) 1997-06, Vol.4 (2), p.161-172
Main Authors: Okamoto, ETSUYA, Kiyosada, TOSHITSUGU, SHIN-ICHIRO Shoda, Kobayashi, SHIRO
Format: Article
Language:English
Subjects:
Acetonitrile
Catalysis
Cellulase
Cellulose
Fluorides
Fungi
Low molecular weights
Oligomers
Polymerization
Stereoselectivity
Substrates
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Summary:Novel cellobiose derivatives, 6-O-methyl, 6′-O-methyl, 6,6′-di-O-methyl- β-cellobiosyl fluorides, have been prepared and their hydrolytic behaviour as well as polymerizability by a purified cellulase from Trichoderma viride were investigated. Among these compounds, 6-O-methyl-β-cellobiosyl fluoride was found to polymerize by the cellulase catalysis in a mixed solvent of acetonitrile and acetate buffer (pH 5.0), giving rise to an alternatingly 6-O-methylated cellulose derivative. The stereoselective formation of the β(1 ← 4) glycosidic bond is explained by a mechanism involving double inversion at the C1 carbon of the substrate. Another cellobiose derivative, 6′O-methyl-β-cellobiosyl fluoride, gave a mixture of low molecular weight oligomers. The difference in the observed polymerizability was explained by assuming a difference in steric repulsions between the methyl groups and an amino acid residue at the enzyme catalytic site
ISSN:0969-0239
1572-882X
DOI:10.1023/A:1018479621509