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

Etsuya Okamoto, Toshitsugu Kiyosada, Shin Ichiro Shoda, Shiro Kobayashi

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46 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)161-172
Number of pages12
JournalCellulose
Volume4
Issue number2
DOIs
Publication statusPublished - 1997

Keywords

  • 6-O-methyl- -cellobiosyl fluoride
  • Alternatingly 6-O-methylated cellulose
  • Cellulase
  • Enzymatic polymerization

ASJC Scopus subject areas

  • Polymers and Plastics

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