2017年
Synthesis of 3-Keto-levoglucosan Using Pyranose Oxidase and Its Spontaneous Decomposition via beta-Elimination
JOURNAL OF APPLIED GLYCOSCIENCE
- 巻
- 64
- 号
- 4
- 開始ページ
- 99
- 終了ページ
- 107
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.5458/jag.jag.JAG-2017_013
- 出版者・発行元
- 日本応用糖質科学会
<p>3-Keto-levoglucosan (3ketoLG) has been postulated to be the product of a reaction catalyzed by levoglucosan dehydrogenase (LGDH), a bacterial enzyme involved in the metabolism of levoglucosan (LG). To investigate the LG metabolic pathway catalyzed by LGDH, 3ketoLG is needed. However, 3ketoLG has not been successfully isolated from the LGDH reaction. This study investigated the ability of pyranose oxidase to convert LG into 3ketoLG by oxidizing the C3 hydroxyl group. During the oxidation of LG, 3ketoLG was spontaneously crystallized in the reaction mixture. Starting with 500 mM LG, the isolation yield of 3ketoLG was 80 %. Nuclear magnetic resonance analyses revealed that a part of 3ketoLG dimerized in aqueous solution, explaining its poor solubility. Even under normal conditions, 3ketoLG was unstable in aqueous solution, with a half-life of 16 h at pH 7.0 and 30 °C. The decomposition proceeded through β-elimination of the C–O bonds at both C1 and C5, as evidenced by decomposition products. This instability explains the difficulty in obtaining 3ketoLG via the LGDH reaction.</p>
- リンク情報
- ID情報
-
- DOI : 10.5458/jag.jag.JAG-2017_013
- ISSN : 1344-7882
- CiNii Articles ID : 130006164490
- Web of Science ID : WOS:000416863300003