Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition Via β-Elimination

Takahito Kajiki; Kazuhiro Yoshinaga; Shiro Komba; Motomitsu Kitaoka

doi:10.5458/jag.jag.JAG-2017_010

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Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition Via β-Elimination

Takahito Kajiki, Kazuhiro Yoshinaga, Shiro Komba, Motomitsu Kitaoka

著者情報

キーワード: 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose, 1,5-anhydro-D-fructose, cellobiose phosphorylase, β-elimination, ascopyrone

ジャーナルフリー早期公開

論文ID: jag.JAG-2017_010

DOI https://doi.org/10.5458/jag.jag.JAG-2017_010

この記事には本公開記事があります。

The final version of this article is now available: Vol. 64 (2017), No. 4

詳細

抄録

Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.

責任著者(Corresponding author)

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