ArticleJournal of applied glycoscience2017
Synthesis of 3-Keto-levoglucosan Using Pyranose Oxidase and Its Spontaneous Decomposition via β-Elimination.
Article in Journal of applied glycoscience, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 9 citations in OpenAlex.
- Comprehensive Analysis of Histidine158 Variants Reveals Histidine Is Essential for Covalent Flavin Attachment in Pyranose 2-Oxidase.Journal of applied glycoscience · 2025Article
- Molecular Basis of Absorption at 340 nm of 3-Ketoglucosides under Alkaline Conditions.Journal of applied glycoscience · 2024Article
- FAD-dependentProceedings of the National Academy of Sciences of the United States of America · 2021Article
- Conversion of levoglucosan into glucose by the coordination of four enzymes through oxidation, elimination, hydration, and reduction.Scientific reports · 2020Article
- Deglycosylation of the IsoflavoneApplied and environmental microbiology · 2020Article
- Epimerization and Decomposition of Kojibiose and Sophorose by Heat Treatment under Neutral pH Conditions.Journal of applied glycoscience · 2019Article
- Identification, functional characterization, and crystal structure determination of bacterial levoglucosan dehydrogenase.The Journal of biological chemistry · 2018Article
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Authors and funding
1 author at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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