Conversion of D-galactose to D-threo-hexos-2,3-diulose by fungal pyranose oxidase

Journal of Carbohydrate Chemistry

Volumn 22, Issue 3-4, 2003, Pages 207-216

  Volc, Jindřich ^a   Sedmera, Petr ^a   Halada, Petr ^a   Dwivedi, Padmanabh ^a,c   Costa Ferreira, Maria ^b  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b INETI   (Portugal)

^c RAJIV GANDHI UNIVERSITY   (India)

Author keywords

D Galactose; D lyxo Hexos 2 ulose; D threo Hexos 2,3 diulose; Oudemansiella mucida; Pyranose dehydrogenase; Pyranose oxidase; Trametes versicolor

Indexed keywords

CARBOHYDRATE DERIVATIVE; FUNGAL ENZYME; GALACTOSE; OXIDOREDUCTASE; PHENYLHYDRAZONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DECARBOXYLATION; DERIVATIZATION; ELUTION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME DEGRADATION; ENZYME PURIFICATION; EVAPORATION; GLUCOSE OXIDATION; INCUBATION TIME; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; TRAMETES VERSICOLOR;

FUNGI; OUDEMANSIELLA MUCIDA; TRAMETES VERSICOLOR;

EID: 0038819616     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120021701     Document Type: Article

References (17)

1. Giffhorn, F.; Köpper, S.; Huwig, A.; Freimund, S. Rare sugars and sugar-based synthons by chemo-enzymatic synthesis. Enzyme Microb. Technol. 2000, 27, 734-742.
2. Giffhorn, F. Fungal pyranose oxidases: occurrence, properties and biotechnical applications in carbohydrate chemistry. Appl. Microbiol. Biotechnol. 2000, 54, 727-740.
3. Volc, J.; Kubátová, E.; Wood, D.; Daniel, G. Pyranose 2-dehydrogenase, a novel sugar oxidoreductase from the basidiomycete fungus Agaricus bisporus. Arch. Microbiol. 1997, 167, 119-125.
4. Ruelius, H.W.; Kerwin, R.M.; Janssen, F.W. Carbohydrate oxidase, a novel enzyme from Polyporus obtusus II. Specificity and characterization of reaction products. Biochim. Biophys. Acta 1968, 167, 501-510.
5. Freimund, S.; Huwig, A.; Giffhorn, F.; Köpper, S. Rare keto-aldoses from enzymatic oxidation: substrates and oxidation products of pyranose 2-oxidase. Chem. Eur. J. 1998, 4 (12), 2442-2455.
6. Volc, J.; Sedmera, P.; Havlíček, V.; Přikrylová, V.; Daniel, G. Conversion of D-glucose to D-erythro-hexos-2,3-diulose (2,3-diketo-D-glucose) by enzyme preparations from the basidiomycete Oudemansiella mucida. Carbohydr. Res. 1995, 278, 59-70.
7. Danneel, H.J.; Rossner, E.; Zeeck, A.; Giffhorn, F. Purification and characterization of pyranose oxidase from the basidiomycete Peniophora gigantea and chemical analyses of its reaction products. Eur. J. Biochem. 1993, 214, 795-802.
8. Masuda-Nishimura, I.; Minamihara, T.; Koyama, Y. Improvement in thermal stability and reactivity of pyranose oxidase from Coriolus versicolor by random mutagenesis. Biotechnol. Lett. 1999, 21, 203-207.
9. Machida, Y.; Nakanishi, T. Purification and properties of pyranose oxidase from Coriolus versicolor. Agr. Biol. Chem. 1984, 48, 2463-2470.
10. Freimund, S.; Huwig, A.; Giffhorn, F.; Köpper, S. Convenient chemo-enzymatic synthesis of D-tagatose. J. Carbohydr. Chem. 1996, 15 (1), 115-120.
11. Haltrich, D.; Leitner, C.; Neuhauser, W.; Nidetzky, B.; Kulbe, K.D.; Volc, J. A convenient enzymatic procedure for the production of aldose free D-tagatose. Ann. N.Y. Acad. Sci. 1998, 864, 296-313.
12. Volc, J.; Sedmera, P.; Halada, P.; Přikrylová, V.; Daniel, G. C-2 and C-3 oxidation of D-Glc, and C-2 oxidation of D-Gal by pyranose dehydrogenase from Agaricus bisporus. Carbohydr. Res. 1998, 310, 151-156.
13. Volc, J.; Kubátová, E.; Daniel, G.; Sedmera, P.; Haltrich, D. Screening of basidiomycete fungi for the quinone-dependent sugar C-2/C-3 oxidoreductase, pyranose dehydrogenase, and properties of the enzyme from Macrolepiota rhacodes. Arch. Microbiol. 2001, 176, 178-186.
14. Volc, J.; Sedmera, P.; Halada, P.; Přikrylová, V.; Haltrich, D. Double oxidation of D-xylose to D-glycero-pentos-2,3-diulose (2,3-diketo-D-xylose) by pyranose dehydrogenase from the mushroom Agaricus bisporus. Carbohydr. Res. 2000, 329, 219-225.
15. Sedmera, P.; Volc, J.; Havlíček, V.; Pakhomova, S.; Jegorov, A. Structural analysis of crystalline D-erythro-hexos-2,3-diulose (2,3-diketo-D-glucose) prepared enzymatically from D-glucose. Carbohydr. Res. 1997, 297, 375-378.
16. Volc, J.; Leitner, C.; Sedmera, P.; Halada, P.; Haltrich, D. Enzymatic formation of dicarbonyl sugars: C-2 Oxidation of 1 → 6 disaccharides gentiobiose, isomaltose and melibiose by pyranose 2-oxidase from Trametes multicolor. J. Carbohydr. Chem. 1999, 18, 999-1007.
17. Volc, J.; Kubátová, E.; Sedmera, P.; Daniel, G.; Gabriel, J. Pyranose oxidase and pyranosone dehydratase: enzymes responsible for conversion of D-glucose to cortalcerone by the basidiomycete Phanerochaete chrysosporium. Arch. Microbiol. 1991, 156, 297-301.