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Gewählte Publikation:

Sedmera, P., Halada, P., Kubátová, E., Haltrich, D., Prikrylová, V., Volc, J..
(2006): New biotransformations of some reducing sugars to the corresponding (di)dehydro(glycosyl) aldoses or aldonic acids using fungal pyranose dehydrogenase
J. Mol. Catal. B: Enzymatic, 41, 32–42 FullText FullText_BOKU

Abstract:
The fungal enzyme pyranose dehydrogenase (PDH) (EC 1.1.99.29) purified to apparent homogeneity from culture media of Agaricus meleagris catalyzed the substrate-dependent C-1, C-2, C-3, C-1,3' or C-2,3(') (di)oxidation of a number of mono- and disaccharides with 1,4-benzoquinone as an electron acceptor. D-Ribose, D-allose, D-gulose and D-talose were oxidized to the corresponding aldonic acids. L-Arabinose was converted exclusively to 2-dehydro-(L)-arabinose ((L)-erythro-pentos-2-ulose) whereas (D)-xylose underwent competing C-2 and C-3 oxidation followed by dioxidation to 2,3-didehydro-(D)-arabinose ((D)-glycero-pentos-2,3-diulose). The major final oxidation products of maltose and cellobiose were the novel compounds 2,3'-didehydromaltose and 2,3'-didehydrocellobiose (alpha- and beta-(D)-ribo-hexos-3-ulopyranosyl-(1 -> 4)-(D)-arabino-hexos-2-ulose), formed via 2- and 3'-monooxidation intermediates. Minor concomitant (di)oxidation at C-1,(3') to the corresponding bionic acids also took place. Maltotriose was preferentially oxidized at C-3 '' of the terminal glucopyranosyl unit and at C-1 of the reducing moiety. The structures of these sugar oxidation products were established by in situ 1D and 2D NMR spectroscopy and ESI-MS. Based on HPLC analysis, conversions of (glycosyl)aldoses in non-buffered systems were nearly quantitative within 3-24 h, depending on the substrate. As the enzyme allows an easy access to highly reactive di- or tricarbonyl sugars, it might become a useful catalyst in carbohydrate chemistry, (c) 2006 Elsevier B.V. All rights reserved.
Autor*innen der BOKU Wien:
Haltrich Dietmar
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Find related publications in this database (Keywords)
aldonic acids
biotransformations
2-dehydro-L-arabinose
dicarbonyl sugars
pyranose dehydrogenase


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