Quantitative Comparison of Pyranose Dehydrogenase Action on Diverse Xylooligosaccharides

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dc.contributorAalto-yliopistofi
dc.contributorAalto Universityen
dc.contributor.authorKarppi, Johannaen_US
dc.contributor.authorZhao, Hongboen_US
dc.contributor.authorChong, Sun Lien_US
dc.contributor.authorKoistinen, Antti E.en_US
dc.contributor.authorTenkanen, Maijaen_US
dc.contributor.authorMaster, Emmaen_US
dc.contributor.departmentDepartment of Bioproducts and Biosystemsen
dc.contributor.groupauthorProtein Technologyen
dc.contributor.organizationUniversity of Helsinkien_US
dc.date.accessioned2020-03-06T15:24:33Z
dc.date.available2020-03-06T15:24:33Z
dc.date.issued2020-01-28en_US
dc.description.abstractPyranose dehydrogenases (PDHs; EC 1.1.99.29; AA3_2) demonstrate ability to oxidize diverse carbohydrates. Previous studies of these enzymes have also uncovered substrate-dependent regioselectivity, along with potential to introduce more than one carbonyl into carbohydrate substrates. Enzymatic oxidation of carbohydrates facilitates their further derivatization or polymerization into bio-based chemicals and materials with higher value; accordingly, PDHs that show activity on xylooligosaccharides could offer a viable approach to extract higher value from hemicelluloses that are typically fragmented during biomass processing. In this study, AbPDH1 from Agaricus bisporus and AmPDH1 from Leucoagaricus meleagris were tested using linear xylooligosaccharides, along with xylooligosaccharides substituted with either arabinofuranosyl or 4-O-(methyl)glucopyranosyluronic acid residues with degree of polymerization of two to five. Reaction products were characterized by HPAEC-PAD to follow substrate depletion, UPLC-MS-ELSD to quantify the multiple oxidation products, and ESI-MSn to reveal oxidized positions. A versatile method based on product reduction using sodium borodeuteride, and applicable to carbohydrate oxidoreductases in general, was established to facilitate the identification and quantification of oxidized products. AbPDH1 activity toward the tested xylooligosaccharides was generally higher than that measured for AmPDH1. In both cases, activity values decreased with increasing length of the xylooligosaccharide and when using acidic rather than neutral substrates; however, AbPDH1 fully oxidized all linear xylooligosaccharides, and 60–100% of all substituted xylooligosaccharides, after 24 h under the tested reaction conditions. Oxidation of linear xylooligosaccharides mostly led to double oxidized products, whereas single oxidized products dominated in reactions containing substituted xylooligosaccharides. Notably, oxidation of specific secondary hydroxyls vs. the reducing end C-1 depended on both the enzyme and the substrate. For all substrates, however, oxidation by both AbPDH1 and AmPDH1 was clearly restricted to the reducing and non-reducing xylopyranosyl residues, where increasing the length of the xylooligosaccharide did not lead to detectable oxidation of internal xylopyranosyl substituents. This detailed analysis of AbPDH1 and AmPDH1 action on diverse xylooligosaccharides reveals an opportunity to synthesize bifunctional molecules directly from hemicellulose fragments, and to enrich for specific products through appropriate PDH selection.en
dc.description.versionPeer revieweden
dc.format.mimetypeapplication/pdfen_US
dc.identifier.citationKarppi, J, Zhao, H, Chong, S L, Koistinen, A E, Tenkanen, M & Master, E 2020, ' Quantitative Comparison of Pyranose Dehydrogenase Action on Diverse Xylooligosaccharides ', Frontiers in Chemistry, vol. 8, 11 . https://doi.org/10.3389/fchem.2020.00011en
dc.identifier.doi10.3389/fchem.2020.00011en_US
dc.identifier.issn2296-2646
dc.identifier.otherPURE UUID: 062a0ad5-0f87-4763-b9bc-7558eff4d63fen_US
dc.identifier.otherPURE ITEMURL: https://research.aalto.fi/en/publications/062a0ad5-0f87-4763-b9bc-7558eff4d63fen_US
dc.identifier.otherPURE LINK: http://www.scopus.com/inward/record.url?scp=85079494630&partnerID=8YFLogxKen_US
dc.identifier.otherPURE FILEURL: https://research.aalto.fi/files/41383882/CHEM_Karppi_et_al_2020_Quantitative_Comparison_ChemProEng.pdfen_US
dc.identifier.urihttps://aaltodoc.aalto.fi/handle/123456789/43365
dc.identifier.urnURN:NBN:fi:aalto-202003062408
dc.language.isoenen
dc.publisherFRONTIERS MEDIA SA
dc.relation.ispartofseriesFrontiers in Chemistryen
dc.relation.ispartofseriesVolume 8en
dc.rightsopenAccessen
dc.subject.keywordcarbohydrate oxidoreductasesen_US
dc.subject.keyworddegree of oxidationen_US
dc.subject.keywordpyranose dehydrogenaseen_US
dc.subject.keywordtelechelic moleculesen_US
dc.subject.keywordxylooligosaccharideen_US
dc.titleQuantitative Comparison of Pyranose Dehydrogenase Action on Diverse Xylooligosaccharidesen
dc.typeA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessäfi
dc.type.versionpublishedVersion
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