Conversion of d-glucose to d-erythro-hexos-2,3-diulose (2,3-diketo-d-glucose) by enzyme preparations from the basidiomycete Oudemansiella mucida

✍ Scribed by Jindřich Volc; Petr Sedmera; Vladimír Havlíček; Věra Přikrylová; Geoffrey Daniel

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 665 KB
• Volume: 278
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00247-3

✦ Synopsis

Aerobic incubation of crude enzyme extracts from the white rot fungus Oudemansiella mucida with o-glucose resulted in transient accumulation of D-arabino-hexos-2-ulose (1, 2-keto-D-glucose) which was subsequently quantitatively converted into a new tricarbonyl sugar metabolite, D-erythro-hexos-2,3-diulose (2, 2,3-diketo-D-glucose). The latter end-product was derivatized with N,N-diphenylhydrazine: its structure was deduced from formulae of the four major hvdrazones isolated from the reaction mixture using thin layer chromatography, and identified by nuclear magnetic resonance and mass spectroscopy. 2 was also obtained on incubations with chemically synthesized 1, and with partially purified preparations of pyranose 2-oxidase. A hypothetical reaction scheme was proposed for two step oxidation of D-glucose to 2 by a single enzyme, pyranose 2-oxidase (EC 1.1.3.1l)).